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Inclusive Leadership Discussion Guide

Part I (June 18, 2020)

Pre-reading

Discussion recording

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Additional resources

Propel crowd-sourced reading/listening list on DEI, anti-racism, inclusive leadership
DEI training and consulting groups: Black Owned DEI Consultants List, Culture Amp, Awaken, Project Include, MESH Diversity, The Rise Journey, Crescendo, LifeLabs Inclusion Audit Tool, Perception Institute, APA Solutions

Ground rules for continuing courageous conversations

Read more about Glenn E. Singleton's framework here.

Courageous conversations are dialogues in which participants commit to engage each other with honesty, open-mindedness, and vulnerability; to listen deeply to better understand each other’s perspective; and to “sustain the conversation when it gets uncomfortable or diverted.”

The goal of Ground Rules for Continuing Courageous Conversations is to be able to have a conversation about race without excessive fear of being labeled racist, biased or bigoted, to avoid blaming or being blamed, and to avoid discounting or invalidating the experiences and feelings of others. To that end, we agree to follow these ground rules:

Four agreements:

1. Stay Engaged

Give yourself permission to focus fully on the conversation topic or exercise at hand.
Share a story, state your opinion, ask a question—risk and grow! Mistakes are part of this work.

2. Speak Your Truth

Honor confidentiality - what is shared here, stays here.
Value everyone’s thoughts.
Start by assuming good intentions.
Speak from your own experience and use “I” statements, as in “I think”, “I feel”, “I believe”, or “I want”
It’s important that we create a safe environment where everyone is free to speak openly.
Keep in mind that people are in different places in this work. In order for us to grow, people need to be able to share thoughts in a way that’s comfortable for them.
Be aware of non-verbal communication.
Before speaking, think about what you want others to know. How can they best hear you?
Mistakes are part of success. Don’t be overly cautious about being politically correct – this is a learning process.
Disagree respectfully.

3. Listen for Understanding

Be comfortable with being uncomfortable
Listen without thinking about how you are going to respond.
Try to understand where another person is coming from as best you can.
Be careful not to compare your experiences with another person’s. This often invalidates or minimizes a person’s experiences.
If someone is pointing out how what you said left them feeling, try not to explain or rationalize what you said or why you said it. Sometimes positive intent is not enough. Sometimes it’s necessary to just say, “I didn’t realize what I said was inappropriate…or hurt you in that way, I’m sorry,” etc.

4. Expect and Accept Non-closure

Engaging in race conversations is ongoing work that does not necessarily leave a person walking away feeling everything turned out the way they hoped. Accept that much of this is about changing yourself, not others.
“Hang out in uncertainty” and not rush to quick solutions, especially in relation to racial understanding, which requires ongoing dialogue.

Responsibility to each other and to the courageous conversation process

Group members will encourage each other to follow the ground rules.

Becoming anti-racist: fear, learning, growth zones

Chart was adapted by Andrew M. Ibrahim MD, MSc from “Who Do I Want to Be During COVID-19” chart (original author unknown) with some ideas pulled from Ibram X. Kendi’s work. https://www.socialwork.career/2020/06/anti-racism-resources-for-social-workers-and-therapists.html

Why be an inclusive leader?

“Diversity” and “inclusion” are so often lumped together that they’re assumed to be the same thing. Diversity speaks to who is on the team, but inclusion focused on who is really in the game.

However, diversity and inclusion alone aren't enough to build a culture that is psychologically safe. In “Belonging: A Conversation about Equity, Diversity, and Inclusion,” Krys Burnette talks about why you need all 3 DEI elements. You can’t only have two elements.

Inclusive leadership is a conglomeration of behaviors such as:

Ensuring that team members speak up and are heard
Making it safe to propose novel ideas
Empowering team members to make decisions
Taking advice and implementing feedback
Giving actionable feedback
Sharing credit for team success

What other tactics can you action to be inclusive?

Authenticity
Networking and visibility
Clear career paths

Definitions from which we can all work for this discussion:

Belonging at work: an outcome of diversity, equity, and inclusion coexisting within teams and an organization; individuals who feel that they belong feel more empowered to speak up, make change, and shift the culture. Leads to resiliency and engagement and therefore everyone is able to achieve better outcomes

Diversity at work: having representation of folks with a variety of identities, backgrounds, and experiences, ideas. This can refer to people of various races, genders, socioeconomic status, sexual orientation, religions, ethnicity, national origins, mental or physical abilities, cognitions, and cultures.

Equity at work: Equity involves trying to understand and give people what they need to enjoy full, healthy lives. Equity at work is committing to constantly and consistently implementing systems and processes that recognize and redistribute power to all individuals, such as ensuring they are able to contribute, obtain professional development, and have clear pathways to leadership

Inclusion at work: ensuring that all individuals feel welcomed, safe, and valued to share their thoughts, ideas, and perspectives

Anti-racism: actively opposing racism by advocating for changes in political, economic, and social life

Bias: associations that people consciously and unconsciously hold. Unconscious or implicit biases are expressed automatically without conscious awareness and may affect our decisions and actions

Anti-bias: acknowledging the existence of biases and actively confronting how they can inform attitudes and actions as individuals, organizations, and a society

Equality: Aims to ensure that everyone gets the same things in order to enjoy full, healthy lives. Like equity, equality aims to promote fairness and justice, but it can only work if everyone starts from the same place and needs the same things

Intersectionality: Intersectionality considers different systems of oppression, and specifically how they overlap and are compounded to shape the employee experience. E.g. when we think about who is in leadership positions, we can't just look at race, we also need to consider other identities such as gender

Race: A socially constructed characterization of individuals based on skin color, culture, etc.

Racism: Any conscious or unconscious act that even unwittingly tolerates, accepts or reinforces racially unequal opportunities or outcomes for an individual or group perceived to have lower racial status. Racism can be individual, institutional, cultural, internalized

Privilege: A right or advantage that is given to some people and not others

“Whiteness”: The component of each and every one of ourselves that expects assimilation to the dominant culture

Small group discussion

Intersectionality

In his recent TED Talk, “The difference between being ‘not racist’ and antiracist,” Ibram X. Kendi says:

“Every race is an intersection of different groups and identities. What’s critical for us to understand is that there hasn’t been just racist ideas that have targeted black people, there are racist ideas that target black women, lesbians, transgender women. There is intersectional bigotry as well.”

7 Circles Activity: Draw a medium-sized circle in the center of a piece of paper. Around that circle, draw seven smaller circles connected to the larger circle. Write your name in the center circle. In the smaller circles, write the names of seven groups with which you identify (examples: gender, nationality/ethnicity, religious affiliation, political stance, geographic ties, family role etc.)

Discussion Question #1:

7 Circles Debrief:

Talk about a time when you felt proud to be a member of a certain group. When did it feel painful to be a member of a certain group?

Discussion Question #2:

Where is there opportunity for you/your company to improve inclusion, equity, belonging, diversity?

Sharing starters - Where is there opportunity for you/your company to improve inclusion, equity, belonging, diversity?

Do these inclusion statements resonate with your experience in the workplace?
Psychological safety
I feel like I belong at my company...
I feel respected by the people I work with....
I know decisions made are inclusive of diverse perspectives...
Incidents
I have witnessed/experienced/overheard harassment based on identity in the past 6 months...
Trust in leadership
I trust that my HR team/Manager/Executive Team will address my concerns swiftly and competently…

Discussion Question #3:

What’s your company’s anti-racism response/action been? Please take notes to share back with the wider group - what responses/systemic change initiatives/ideas in progress did you find inclusive?

Discussion Question #4:

How do you think about being an inclusive leader, mentor, teammate? See Deepa Iyer’s list of roles in social change ecosystems on the next page. If you have started to fill out the Reflection Guide in the PDF, think about referencing some thoughts you have from that worksheet.

The Roles

Weavers: I see the through-lines of connectivity between people, places, organizations, ideas, and movements.
Experimenters: I innovate, pioneer, and invent. I take risks and course-correct as needed.
Frontline Responders: I address community crises by marshaling and organizing resources, networks, and messages.
Visionaries: I imagine and generate our boldest possibilities, hopes and dreams, and remind us of our direction.
Builders: I develop, organize, and implement ideas, practices, people, and resources in service of a collective vision.
Caregivers: I nurture and nourish the people around me by creating and sustaining a community of care, joy, and connection.
Disruptors: I take uncomfortable and risky actions to shake up the status quo, to raise awareness, and to build power.
Healers: I recognize and tend to the generational and current traumas caused by oppressive systems, institutions, policies, and practices.
Storytellers: I craft and share our community stories, cultures, experiences, histories, and possibilities through art, music, media, and movement.
Guides: I teach, counsel, and advise, using my gifts of well-earned discernment and wisdom.z

Emily Pik

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Scott Belsky’s Elephant List

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Jun 18

What Makes an Effective Executive

Summary. Reprint: R0406C An effective executive does not need to be a leader in the typical sense of the word. Peter Drucker, the author of more than two dozen HBR articles, says some of the best business and nonprofit CEOs he has worked...

An effective executive does not need to be a leader in the sense that the term is now most commonly used. Harry Truman did not have one ounce of charisma, for example, yet he was among the most effective chief executives in U.S. history. Similarly, some of the best business and nonprofit CEOs I’ve worked with over a 65-year consulting career were not stereotypical leaders. They were all over the map in terms of their personalities, attitudes, values, strengths, and weaknesses. They ranged from extroverted to nearly reclusive, from easygoing to controlling, from generous to parsimonious.

What made them all effective is that they followed the same eight practices:

They asked, “What needs to be done?”
They asked, “What is right for the enterprise?”
They developed action plans.
They took responsibility for decisions.
They took responsibility for communicating.
They were focused on opportunities rather than problems.
They ran productive meetings.
They thought and said “we” rather than “I.”

The first two practices gave them the knowledge they needed. The next four helped them convert this knowledge into effective action. The last two ensured that the whole organization felt responsible and accountable.

Get the Knowledge You Need

The first practice is to ask what needs to be done. Note that the question is not “What do I want to do?” Asking what has to be done, and taking the question seriously, is crucial for managerial success. Failure to ask this question will render even the ablest executive ineffectual.

Asking what has to be done, and taking the question seriously, is crucial for managerial success.

When Truman became president in 1945, he knew exactly what he wanted to do: complete the economic and social reforms of Roosevelt’s New Deal, which had been deferred by World War II. As soon as he asked what needed to be done, though, Truman realized that foreign affairs had absolute priority. He organized his working day so that it began with tutorials on foreign policy by the secretaries of state and defense. As a result, he became the most effective president in foreign affairs the United States has ever known. He contained Communism in both Europe and Asia and, with the Marshall Plan, triggered 50 years of worldwide economic growth.

Similarly, Jack Welch realized that what needed to be done at General Electric when he took over as chief executive was not the overseas expansion he wanted to launch. It was getting rid of GE businesses that, no matter how profitable, could not be number one or number two in their industries.

The answer to the question “What needs to be done?” almost always contains more than one urgent task. But effective executives do not splinter themselves. They concentrate on one task if at all possible. If they are among those people—a sizable minority—who work best with a change of pace in their working day, they pick two tasks. I have never encountered an executive who remains effective while tackling more than two tasks at a time. Hence, after asking what needs to be done, the effective executive sets priorities and sticks to them. For a CEO, the priority task might be redefining the company’s mission. For a unit head, it might be redefining the unit’s relationship with headquarters. Other tasks, no matter how important or appealing, are postponed. However, after completing the original top-priority task, the executive resets priorities rather than moving on to number two from the original list. He asks, “What must be done now?” This generally results in new and different priorities.

To refer again to America’s best-known CEO: Every five years, according to his autobiography, Jack Welch asked himself, “What needs to be done now?” And every time, he came up with a new and different priority.

But Welch also thought through another issue before deciding where to concentrate his efforts for the next five years. He asked himself which of the two or three tasks at the top of the list he himself was best suited to undertake. Then he concentrated on that task; the others he delegated. Effective executives try to focus on jobs they’ll do especially well. They know that enterprises perform if top management performs—and don’t if it doesn’t.

Effective executives’ second practice—fully as important as the first—is to ask, “Is this the right thing for the enterprise?” They do not ask if it’s right for the owners, the stock price, the employees, or the executives. Of course they know that shareholders, employees, and executives are important constituencies who have to support a decision, or at least acquiesce in it, if the choice is to be effective. They know that the share price is important not only for the shareholders but also for the enterprise, since the price/earnings ratio sets the cost of capital. But they also know that a decision that isn’t right for the enterprise will ultimately not be right for any of the stakeholders.

This second practice is especially important for executives at family owned or family run businesses—the majority of businesses in every country—particularly when they’re making decisions about people. In the successful family company, a relative is promoted only if he or she is measurably superior to all nonrelatives on the same level. At DuPont, for instance, all top managers (except the controller and lawyer) were family members in the early years when the firm was run as a family business. All male descendants of the founders were entitled to entry-level jobs at the company. Beyond the entrance level, a family member got a promotion only if a panel composed primarily of nonfamily managers judged the person to be superior in ability and performance to all other employees at the same level. The same rule was observed for a century in the highly successful British family business J. Lyons & Company (now part of a major conglomerate) when it dominated the British food-service and hotel industries.

Asking “What is right for the enterprise?” does not guarantee that the right decision will be made. Even the most brilliant executive is human and thus prone to mistakes and prejudices. But failure to ask the question virtually guarantees the wrong decision.

Write an Action Plan

Executives are doers; they execute. Knowledge is useless to executives until it has been translated into deeds. But before springing into action, the executive needs to plan his course. He needs to think about desired results, probable restraints, future revisions, check-in points, and implications for how he’ll spend his time.

First, the executive defines desired results by asking: “What contributions should the enterprise expect from me over the next 18 months to two years? What results will I commit to? With what deadlines?” Then he considers the restraints on action: “Is this course of action ethical? Is it acceptable within the organization? Is it legal? Is it compatible with the mission, values, and policies of the organization?” Affirmative answers don’t guarantee that the action will be effective. But violating these restraints is certain to make it both wrong and ineffectual.

The action plan is a statement of intentions rather than a commitment. It must not become a straitjacket. It should be revised often, because every success creates new opportunities. So does every failure. The same is true for changes in the business environment, in the market, and especially in people within the enterprise—all these changes demand that the plan be revised. A written plan should anticipate the need for flexibility.

In addition, the action plan needs to create a system for checking the results against the expectations. Effective executives usually build two such checks into their action plans. The first check comes halfway through the plan’s time period; for example, at nine months. The second occurs at the end, before the next action plan is drawn up.

Finally, the action plan has to become the basis for the executive’s time management. Time is an executive’s scarcest and most precious resource. And organizations—whether government agencies, businesses, or nonprofits—are inherently time wasters. The action plan will prove useless unless it’s allowed to determine how the executive spends his or her time.

Napoleon allegedly said that no successful battle ever followed its plan. Yet Napoleon also planned every one of his battles, far more meticulously than any earlier general had done. Without an action plan, the executive becomes a prisoner of events. And without check-ins to reexamine the plan as events unfold, the executive has no way of knowing which events really matter and which are only noise.

Act

When they translate plans into action, executives need to pay particular attention to decision making, communication, opportunities (as opposed to problems), and meetings. I’ll consider these one at a time.

Take responsibility for decisions.

A decision has not been made until people know:

the name of the person accountable for carrying it out;
the deadline;
the names of the people who will be affected by the decision and therefore have to know about, understand, and approve it—or at least not be strongly opposed to it—and
the names of the people who have to be informed of the decision, even if they are not directly affected by it.

An extraordinary number of organizational decisions run into trouble because these bases aren’t covered. One of my clients, 30 years ago, lost its leadership position in the fast-growing Japanese market because the company, after deciding to enter into a joint venture with a new Japanese partner, never made clear who was to inform the purchasing agents that the partner defined its specifications in meters and kilograms rather than feet and pounds—and nobody ever did relay that information.

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It’s just as important to review decisions periodically—at a time that’s been agreed on in advance—as it is to make them carefully in the first place. That way, a poor decision can be corrected before it does real damage. These reviews can cover anything from the results to the assumptions underlying the decision.

Such a review is especially important for the most crucial and most difficult of all decisions, the ones about hiring or promoting people. Studies of decisions about people show that only one-third of such choices turn out to be truly successful. One-third are likely to be draws—neither successes nor outright failures. And one-third are failures, pure and simple. Effective executives know this and check up (six to nine months later) on the results of their people decisions. If they find that a decision has not had the desired results, they don’t conclude that the person has not performed. They conclude, instead, that they themselves made a mistake. In a well-managed enterprise, it is understood that people who fail in a new job, especially after a promotion, may not be the ones to blame.

Executives also owe it to the organization and to their fellow workers not to tolerate nonperforming individuals in important jobs. It may not be the employees’ fault that they are underperforming, but even so, they have to be removed. People who have failed in a new job should be given the choice to go back to a job at their former level and salary. This option is rarely exercised; such people, as a rule, leave voluntarily, at least when their employers are U.S. firms. But the very existence of the option can have a powerful effect, encouraging people to leave safe, comfortable jobs and take risky new assignments. The organization’s performance depends on employees’ willingness to take such chances.

Executives owe it to the organization and their fellow workers not to tolerate nonperforming people in important jobs.

A systematic decision review can be a powerful tool for self-development, too. Checking the results of a decision against its expectations shows executives what their strengths are, where they need to improve, and where they lack knowledge or information. It shows them their biases. Very often it shows them that their decisions didn’t produce results because they didn’t put the right people on the job. Allocating the best people to the right positions is a crucial, tough job that many executives slight, in part because the best people are already too busy. Systematic decision review also shows executives their own weaknesses, particularly the areas in which they are simply incompetent. In these areas, smart executives don’t make decisions or take actions. They delegate. Everyone has such areas; there’s no such thing as a universal executive genius.

In areas where they are simply incompetent, smart executives don’t make decisions or take actions. They delegate. Everyone has such areas.

Most discussions of decision making assume that only senior executives make decisions or that only senior executives’ decisions matter. This is a dangerous mistake. Decisions are made at every level of the organization, beginning with individual professional contributors and frontline supervisors. These apparently low-level decisions are extremely important in a knowledge-based organization. Knowledge workers are supposed to know more about their areas of specialization—for example, tax accounting—than anybody else, so their decisions are likely to have an impact throughout the company. Making good decisions is a crucial skill at every level. It needs to be taught explicitly to everyone in organizations that are based on knowledge.

Take responsibility for communicating.

Effective executives make sure that both their action plans and their information needs are understood. Specifically, this means that they share their plans with and ask for comments from all their colleagues—superiors, subordinates, and peers. At the same time, they let each person know what information they’ll need to get the job done. The information flow from subordinate to boss is usually what gets the most attention. But executives need to pay equal attention to peers’ and superiors’ information needs.

We all know, thanks to Chester Barnard’s 1938 classic The Functions of the Executive, that organizations are held together by information rather than by ownership or command. Still, far too many executives behave as if information and its flow were the job of the information specialist—for example, the accountant. As a result, they get an enormous amount of data they do not need and cannot use, but little of the information they do need. The best way around this problem is for each executive to identify the information he needs, ask for it, and keep pushing until he gets it.

Focus on opportunities.

Good executives focus on opportunities rather than problems. Problems have to be taken care of, of course; they must not be swept under the rug. But problem solving, however necessary, does not produce results. It prevents damage. Exploiting opportunities produces results.

Above all, effective executives treat change as an opportunity rather than a threat. They systematically look at changes, inside and outside the corporation, and ask, “How can we exploit this change as an opportunity for our enterprise?” Specifically, executives scan these seven situations for opportunities:

an unexpected success or failure in their own enterprise, in a competing enterprise, or in the industry;
a gap between what is and what could be in a market, process, product, or service (for example, in the nineteenth century, the paper industry concentrated on the 10% of each tree that became wood pulp and totally neglected the possibilities in the remaining 90%, which became waste);
innovation in a process, product, or service, whether inside or outside the enterprise or its industry;
changes in industry structure and market structure;
demographics;
changes in mind-set, values, perception, mood, or meaning; and
new knowledge or a new technology.

Effective executives also make sure that problems do not overwhelm opportunities. In most companies, the first page of the monthly management report lists key problems. It’s far wiser to list opportunities on the first page and leave problems for the second page. Unless there is a true catastrophe, problems are not discussed in management meetings until opportunities have been analyzed and properly dealt with.

Staffing is another important aspect of being opportunity focused. Effective executives put their best people on opportunities rather than on problems. One way to staff for opportunities is to ask each member of the management group to prepare two lists every six months—a list of opportunities for the entire enterprise and a list of the best-performing people throughout the enterprise. These are discussed, then melded into two master lists, and the best people are matched with the best opportunities. In Japan, by the way, this matchup is considered a major HR task in a big corporation or government department; that practice is one of the key strengths of Japanese business.

Make meetings productive.

The most visible, powerful, and, arguably, effective nongovernmental executive in the America of World War II and the years thereafter was not a businessman. It was Francis Cardinal Spellman, the head of the Roman Catholic Archdiocese of New York and adviser to several U.S. presidents. When Spellman took over, the diocese was bankrupt and totally demoralized. His successor inherited the leadership position in the American Catholic church. Spellman often said that during his waking hours he was alone only twice each day, for 25 minutes each time: when he said Mass in his private chapel after getting up in the morning and when he said his evening prayers before going to bed. Otherwise he was always with people in a meeting, starting at breakfast with one Catholic organization and ending at dinner with another.

Top executives aren’t quite as imprisoned as the archbishop of a major Catholic diocese. But every study of the executive workday has found that even junior executives and professionals are with other people—that is, in a meeting of some sort—more than half of every business day. The only exceptions are a few senior researchers. Even a conversation with only one other person is a meeting. Hence, if they are to be effective, executives must make meetings productive. They must make sure that meetings are work sessions rather than bull sessions.

The key to running an effective meeting is to decide in advance what kind of meeting it will be. Different kinds of meetings require different forms of preparation and different results:

A meeting to prepare a statement, an announcement, or a press release.

For this to be productive, one member has to prepare a draft beforehand. At the meeting’s end, a preappointed member has to take responsibility for disseminating the final text.

A meeting to make an announcement—for example, an organizational change.

This meeting should be confined to the announcement and a discussion about it.

A meeting in which one member reports.

Nothing but the report should be discussed.

A meeting in which several or all members report.

Either there should be no discussion at all or the discussion should be limited to questions for clarification. Alternatively, for each report there could be a short discussion in which all participants may ask questions. If this is the format, the reports should be distributed to all participants well before the meeting. At this kind of meeting, each report should be limited to a preset time—for example, 15 minutes.

A meeting to inform the convening executive.

The executive should listen and ask questions. He or she should sum up but not make a presentation.

A meeting whose only function is to allow the participants to be in the executive’s presence.

Cardinal Spellman’s breakfast and dinner meetings were of that kind. There is no way to make these meetings productive. They are the penalties of rank. Senior executives are effective to the extent to which they can prevent such meetings from encroaching on their workdays. Spellman, for instance, was effective in large part because he confined such meetings to breakfast and dinner and kept the rest of his working day free of them.

Making a meeting productive takes a good deal of self-discipline. It requires that executives determine what kind of meeting is appropriate and then stick to that format. It’s also necessary to terminate the meeting as soon as its specific purpose has been accomplished. Good executives don’t raise another matter for discussion. They sum up and adjourn.

Good follow-up is just as important as the meeting itself. The great master of follow-up was Alfred Sloan, the most effective business executive I have ever known. Sloan, who headed General Motors from the 1920s until the 1950s, spent most of his six working days a week in meetings—three days a week in formal committee meetings with a set membership, the other three days in ad hoc meetings with individual GM executives or with a small group of executives. At the beginning of a formal meeting, Sloan announced the meeting’s purpose. He then listened. He never took notes and he rarely spoke except to clarify a confusing point. At the end he summed up, thanked the participants, and left. Then he immediately wrote a short memo addressed to one attendee of the meeting. In that note, he summarized the discussion and its conclusions and spelled out any work assignment decided upon in the meeting (including a decision to hold another meeting on the subject or to study an issue). He specified the deadline and the executive who was to be accountable for the assignment. He sent a copy of the memo to everyone who’d been present at the meeting. It was through these memos—each a small masterpiece—that Sloan made himself into an outstandingly effective executive.

Effective executives know that any given meeting is either productive or a total waste of time.

Think and Say “We”

The final practice is this: Don’t think or say “I.” Think and say “we.” Effective executives know that they have ultimate responsibility, which can be neither shared nor delegated. But they have authority only because they have the trust of the organization. This means that they think of the needs and the opportunities of the organization before they think of their own needs and opportunities. This one may sound simple; it isn’t, but it needs to be strictly observed.

We’ve just reviewed eight practices of effective executives. I’m going to throw in one final, bonus practice. This one’s so important that I’ll elevate it to the level of a rule: Listen first, speak last.

Effective executives differ widely in their personalities, strengths, weaknesses, values, and beliefs. All they have in common is that they get the right things done. Some are born effective. But the demand is much too great to be satisfied by extraordinary talent. Effectiveness is a discipline. And, like every discipline, effectiveness can be learned and must be earned.

HBR

Jun 18

So, You've Accepted a Corporate Chief of Staff Role - Now What? (Part 4) - Tyler Parris

http://wordclouds.com

This article is the fourth in a five-part series on what you most need to focus on to succeed as a corporate chief of staff. In research for my upcoming book, Chief of Staff: The Strategic Partner Who Will Revolutionize Your Organization, I interviewed scores of corporate chiefs of staff, C-suite executives, and HR executives around the globe and across industries. I studied thousands more. Five imperatives for new corporate chiefs of staff emerged from that research:

Establish and maintain trust with your executive and his or her direct reports.
Establish yourself as the executive’s proxy and information funnel, filter, facilitator.
Establish yourself as the executive’s thought partner.
Identify and choose the projects that you can own from beginning to end, and deliver them.
Take care of yourself.

Identify and choose projects that you can own from beginning to end, and deliver them

Before I go too far in explaining the importance of this topic, keep in mind that many people come through a rotational version of the chief of staff role, with an eye toward general management or executive positions once they have completed 24–36 months in the role. Others are long-term or career chiefs of staff who spend five years to the rest of their careers in the role. You can take something from this post no matter which model you find yourself in, but what you take will likely be different.

In the early conversations in which you and your executive are exchanging expectations, ensure that one of you can identify a few special projects that you will own and drive during your tenure. Doing so enables your executive to focus on his or her highest and best use of time (usually big-picture, strategic thinking versus project details) and manage cross-functional work for which there is no clear departmental owner. Owning projects from beginning to end serves your needs, too, because these projects do the following:

Establish your leadership presence and give you visibility at the executive level, especially when a lot of your work in the role is behind the scenes
Keep you engaged in and motivated by your work, especially when a lot of your work will be focused on long-term goals
Set you up for success in your performance reviews in the role and as you target your next role

Establishing your leadership presence and visibility

One chief of staff articulated the challenge beautifully: “In this role, there are elements of ownership, but for the most part your boss is your project, and you don’t control him. You help create the canvas on which he paints, but you don’t do a lot of the painting.” Stepping out from behind the scenes into the spotlight occasionally helps create your own leadership brand and keeps your own identity distinct from your executive’s. Some chiefs of staff, especially those who serve more than one leader or in multiple chief of staff roles, can get “pigeonholed” into staying in the role; and once that happens, they might have to leave the company to break out of the reputation of being “just” a chief of staff. You need direct, tangible business achievements to establish yourself as a leader in your own right.

Keeping engaged in and motivated by your work

Progress in this role is often measured over the long term (months or years). Many of the projects you start will not be fulfilled in your tenure. Having some ownership of short-term projects can provide you some successes along the way that can keep you engaged or prevent you from being discouraged when it feels like achievement, or even progress, is far away.

Setting yourself up for success in the role and beyond

One of the biggest challenges for chiefs of staff in the role is how to rate themselves in annual performance reviews. “Many companies allocate bonuses and stock options based on peer-to-peer comparison, which isn’t possible because one chief of staff isn’t the same from one department to another, let alone one company to another or one industry to another,” says one high-tech chief of staff. “If you have a chief of staff who is compared with sales people, the sales people can point to more tangible dollar results, so managing your review can be tricky.” Beyond this year’s performance review, especially for the rotational chief of staff, you deal with the challenge that the spotlight (and the seven-figure salary) hits the leader, not the chief of staff. If you are in the background, you often don’t get the credit; so what do you put on your resume? How do you articulate the concrete contributions that you made when you apply for that director of investor relations role or that GM of facilities role? Owning projects gives you those concrete contributions to point to.

It’s important to note that you might not own a lot of projects as a chief of staff – you’ll influence, facilitate, orchestrate, provide frameworks for, and oversee others who are on the hook for their projects more often than not. Additionally, I found multiple instances in my research where the role failed because the incumbent came into the role expecting to own projects and be in the spotlight. Still, carving out a few projects that you can own will likely make a big difference.

Here are examples of some special projects that were highlighted by chiefs of staff in my interviews:

A review and restructuring of executive compensation packages
Organizational restructuring, with or without layoffs
Creating frameworks for new business models or determining which business models the company will move forward with
Assessment of specific merger and acquisition opportunities
A revamp of planning and budgeting processes
A comprehensive business review of core functions
Formulation of a strategy and program for the company’s women in leadership
Bringing together a cross-functional team to revamp investor reporting
Orchestrating a litigation framework and governance process that enabled a company to proactively decide on what intellectual property lawsuits it would pursue to protect its interests
Creation of and representation in governance processes

One chief of staff for a high-tech company spent a fair amount of his first two weeks ensuring the flawless execution of a day-long meeting with 30 Chinese delegates and some executives from a major U.S. aerospace company, making sure that the right folks were where they needed to be, presentation content was delivered in Chinese and English, and dinner and other logistics went smoothly. He did all this while preparing himself and his executive for an upcoming board meeting, getting to know the team, and learning the daily tasks and ongoing projects that he’d need to attend to. This project showed that he could deliver, on short notice and without knowing all the players and pieces to start, and began what was by all accounts a very successful stint in the role.

In the next and final article in this series, I’ll look at the importance of taking care of yourself in a role in which you don’t fully own your own schedule.

I help people in chief of staff roles increase their impact, extend their influence, and shorten their learning curve so they can succeed in this role and future leadership roles that they'll step into. If you're a corporate, nonprofit, academic, or government chief of staff, stop by https://chiefofstaff.expert and make it your "home on the web" while you're in the role.

Jun 18

How to Build Remote and Distributed Teams

Jun 18

Writing a Business Plan

Jun 18

Step-by-Step Exercises to Define Your Product Strategy

Jun 18

Work-life. Balance.

America needs Paid Family Leave. Fathers need to use it.

Serena only saw me on weekends for the first eight months of her pregnancy. I missed a lot of doctor’s appointments because I was deep in my third year back at Reddit in the midst of a big turnaround project that started in 2014. She was in Florida. I had to be everywhere else: San Francisco, New York, Los Angeles — anywhere our biggest clients were. I was fighting alongside our sales, communications, and business development teams to win deals and restore Reddit’s brand. I felt terrible about it. She never gave me a hard time, but I know it was frustrating for her.

We were both relieved when I took off a few weeks before Alexis Olympia Ohanian Jr. was due. I dropped by CNBC to do some press just beforehand and was impromptu asked by Becky Quick about whether I’d be taking time off and I proudly said I would be. I said I was doing it selfishly, because I knew this was going to be an important time in my family’s life and I wanted all my employees (and industry) to see that it mattered, even for a career-driven entrepreneur.

I had no idea how grateful I would be for our policy, or my ability to make full use of it. Years before I was anxiously sitting in that delivery room, Reddit’s vice president of people and culture, Katelin Holloway, sat down and reviewed her plan with me for our Paid Family Leave policy at Reddit. I don’t remember anything in particular about the meeting other than it all sounded reasonable. Now I can’t imagine anyone having a child without it.

The birth of our daughter nearly killed Serena. When she was released a few days later, there was still an open wound from the C-section that needed to be repacked with fresh gauze every day for the next few weeks as she recovered.

With every advantage imaginable — money, family support, both of us being our own bosses, and my 16 weeks of Paid Family Leave — it was still a traumatic period in our lives; I couldn’t imagine going through it without having the peace of mind Paid Family Leave provided.

1 in 4 US women are back at work within 2 weeks of giving birth.

This is unacceptable. We need a federal law to fix the fact that we’re the last developed nation in the world without a Paid Family Leave policy. I wrote about it for the first time in The Hill back in July 2018 and it caused quite a stir. People kept asking me about it. What was next? I’d connected with PL+US, who are leading the fight to get it for all Americans by 2022.

Companies live or die because of the talent they can attract and retain, so this arms race for family benefits is quickly gaining momentum beyond the tech industry. Dove Men+Care stepped up to create a fund to encourage men in particular to step up and take their leave if they’re lucky to have access to it (and even paid them if they didn’t). Last month, Sweetgreen, a fast-casual salad restaurant chain, announced 5 months of paid parental leave, while just last week, Target expanded their family leave benefits, including part-time workers. It’s not a question of if this will become available to all Americans, it’s a question of when.

Business men have long separated themselves from their family life, yet we work in order to help support those families; this is an important sense of purpose that the modern workforce is increasingly happy to blend: the Business Dad. Venture capital firms are no exception, so I brought the same Paid Family Leave policy over to Initialized when I returned full-time. Garry and I proudly offer 16 weeks of Paid Family Leave following the birth or adoption of a child.

I’m thrilled to say my co-founder Garry Tan, partner Eric Woersching, and our newest hire, fund controller Robert Lindsey, have all taken Paid Family Leave this spring and summer. Yes, the firm’s co-founder and one of our investing partners are all celebrating this Father’s day on Paid Leave. I encourage all of our new dads to take their full leave, because it de-stigmatizes pregnancy-in-the-workforce for our female colleagues.

In fact, we strongly encourage our portfolio companies to adopt family leave policies that are appropriate for their funding stage and team size; which typically mean having a policy in place once they’ve found some stability post-product-market fit and have raised a Series A.

But in many cases, we see Initialized founders proactively offering paid leave even at the earliest stages. One of our founders, Eli Brown, the CEO of Guilded, had to make a tough hiring decision shortly after raising their seed round — they wanted to hire a candidate who was going to immediately have a child upon joining.

He decided to extend them an offer, and after joining and taking six weeks of Paid Family Leave, they’re still with the company today. In retrospect, he felt that this was the right decision:

“Paid Family Leave is one of those cases where doing the right thing is also the best thing to do for your company,” he said “People do their best work when they feel like their company cares about them, and a company that cares supports people during important events in their lives.”

Another one of our founders, Brandon Rodman, CEO of Weave (initialized 2014), recently shared this email an employee sent him:

I just wanted to say thank you for the blessing it is to work at Weave. I’m especially thankful for the paternity/maternity plan we offer here!Our new baby girl, Emery, was born May 13th and on May 16th we discovered she had 3 major heart defects. Basically, she was born with half a working heart. Not the easiest way to come into parenthood.

We were life-flighted to Primary Children’s in SLC and she underwent extensive heart surgery and has been in recovery since today. She is doing awesome and is so strong!I just don’t know a company who allows the dad to stay home for 6 weeks! Because of that I was able to stay close to her 24/7 and supporting my wife in this hard time. The food delivery, the diapers have been fantastic!Weave is one of the best things that has happened to me and to my family, and I am so grateful for your vision on “People, not Employees” and always wanting family to be first! I cannot thank you enough!”

Flexibility in particular makes a difference for new dads. A new study by Stanford economists shows that giving fathers flexibility to take time off work in the months after their children are born improves the postpartum health and mental well-being of mothers.

Sadly, of the only 1 in 5 American dads who have access to paid leave, many of them are too nervous to utilize it. According to PL+US research, of the men planning to take leave, only 50% believe their employer supports them and nearly one-third of dads think that taking leave could negatively impact their career. That’s one reason why I’ve been so outspoken and I think this upcoming Father’s Day is a great opportunity to rally around this idea and join us in taking more steps toward real and lasting change.

Until the government catches up and passes a federal Paid Family Leave policy, it’s on businesses to offer comprehensive, and inclusive Paid Family Leave. We’ve shared Initialized’s family leave policy below so you can copy and paste it, and then hopefully improve upon it. Our friends at PL+US are also willing to do free consulting for you and your company to implement a great Paid Family Leave policy — contact them here and tell them I sent you! They also have many other resources for business leaders on their website that are worth looking into.

Whether you’re a parent or not, if you value being able to integrate work and family life in a healthy way in this country, there are several things you can do to push policy and the conversation forward. You can recruit other fathers and even write your member of Congress here. We’ll be lobbying them in D.C. this October, backed by hundreds of thousands of you.

If you’re a dad, I encourage you to become a #Dadvocate. Share your story of being a dad — whether you took Paid Family Leave or not — and encourage other dads to do the same. You can find more about the #Dadvocate campaign here.

I’ll leave you with one last tip and it sounds simple but it’s powerful — ask dads about dad things, especially at work. Trust me, do it while you’re making small talk at the fridge; he’ll be happy to answer a question like “Hey, what’s your two-year-old into these days?” (Answer: Olympia loves fish right now, she waves to them while she walks by the long aquarium tanks as if she’s greeting a crowd from her float in a parade). The more we normalize dads just being dads (and not “babysitting” their kids as the tabloids sometimes suggest), the sooner we can shift the culture and ultimately the law.

_The Initialized Capital sample Paid Family Leave polic_y

Eligibility

A full-time exempt employee who has worked for the Company for at least six months and who wishes to: take bonding time with his/her new baby (or newly adopted child Feb. 2018 who is either under 18 years of age or a special needs child); or assist a spouse or domestic partner with pre- or post-natal childcare, may take a paid family leave of up to sixteen consecutive weeks. Leave time under this policy will be paid, subject to the paragraph below. Family leave can begin up to one month prior to the birth (or adoption) of a child, but cannot commence later than eight months after the birth (or adoption) of a child. During family leave, an employee will be paid at the salary rate he or she was paid just prior to the commencement of the leave. An employee planning a family leave should coordinate with his or her manager in advance to determine leave and return dates, and to ensure the smooth transition of duties.

Coordination with State Benefits

“Paid Family Leave” (PFL) is a component of California’s state disability insurance program (SDI). Employees covered by SDI are also eligible for PFL, meaning they can receive a benefit from the state of up to six weeks of salary. The Company requires that an employee taking paid family leave apply for the California state PFL benefit in advance of taking family leave, and as such, will not pay the employee for the first six weeks of family leave (unless such employee is not eligible for the full PFL benefit, for reasons that are not the fault of such employee). Employees are advised to consult with the Head of Finance well in advance of taking a paid family leave, to ensure that PFL benefits can be properly claimed.

Benefit Plans

The Company will continue to pay for the employee’s participation in the Company’s group health plans to the same extent and under the same terms and conditions as would apply had the employee not taken family leave, up to a maximum of 16 weeks per family leave.

Return to Work

An Employee returning from paid family leave will be reinstated to the same position he or she held prior to the leave, unless the position no longer exists for reasons unrelated to the leave. In such a situation, an employee will be reinstated to a similar position with similar pay and benefits. Failure to return to work or request an extension of leave time at the conclusion of the leave may result in the loss of reemployment rights, unless the reason for the employee’s inability to return is legally protected.

Initialized Capital

Jun 18

Initial Interview Email

Jun 18

Reference Checks

Jun 18

Doing the Enough Thing

Jun 18

Three Buckets

Jun 18

Why do new leaders need a coach?

Jun 18

Sales Advice for Technical Founders

Jun 18

The ultimate guide to remote work

Jun 18

10 Things We Know About the Science of Meditation

Jun 18

Black History Month Programming Tips and Resources

https://www.jopwell.com/thewell/posts/black-history-month-programming-tips-and-resources

Written by Tani Brown, Head of Community at Jopwell

The origins of Black History Month date back to 1926 when historian Carter G. Woodson began designating the second week in February as "Negro History Week." Woodson was one of the first widely recognized scholars of African diaspora and African-American history at a time when the contributions of African-Americans were largely being misrepresented and ignored in the narrative of U.S. history.

The second week of February symbolically coincided with the birthdays of Abraham Lincoln (February 12) and Frederick Douglass (February 14), both notable figures which held great significance to the Black community and had been widely celebrated together since the late 19th century.

Today, Black History Month is a federally recognized, nationwide celebration that provides the opportunity for all to promote and educate achievements by Black Americans and peoples of African descent. In 2021, Black History Month presents workplaces with a distinct opportunity to elevate Black voices and achievements. It’s also a great opportunity to “enter the conversation” -- especially if you’ve been nervous or unprepared to do so previously. Here at Jopwell, we believe that every month is Black History Month just as Black History is American history, but we recognize the benefits of formal recognition and acknowledgment of BHM.

With that, here are some tips for developing your Black History Month programming.

Go beyond the token moment

Avoid performance-level activism. Don’t share a picture of Martin Luther King Jr. or Maya Angelou without regard for historical and present day context. Be wary of how your written and verbal statements frame the achievements of an individual, cause, or movement. Awareness months are opportunities to show that your organization values the advancement of diversity, equity, and inclusion. How does the recognition and acknowledgement you’re sharing inform the mission and values of your organization?

Design for relevance

Ask yourself - what is the company trying to achieve with Black History Month programming? Do you have company goals that you are trying to amplify through your messaging? Do you want to share the benefits of having specific perspectives at the table? Are there causes your leadership wants to champion? Outline specific goals, and make those goals known org wide! Normalize highlighting experts in their specific fields (that happen to self-identify as underrepresented), compensate them, and bring them in year-round – outside of Black History Month. Especially if you are in an industry that has been slow to recognize minority movements, bring awareness to milestones, firsts, and achievements of diverse groups within that industry.

Ask but do not assign

Announce that your organization is investing in Black History Month, but do not automatically assume your Black employees are responsible for ownership of programming. Many Black employees often lament that they are asked to essentially work for free during Black History Month as knowledge and culture experts. There are a myriad of issues with this assumption, but the most harmful is the perpetuation of the pay-opportunity gap disparity that minority awareness months are meant to draw attention to. Diversity without inclusion. Symbolism without meaning. Action without accountability. Ask ALL employees if they would like to support and reward them for their time with compensation, recognition, and acknowledgement.

Consistency over intensity

Invest, don’t just show up, to affinity history months. The urgency that companies and their teams feel around Black History Month is the consistency they should aim for year-round. Aim for steadiness over perfunctory actions; it’s the key towards shifting your organization from a reactive observer to an active participant in the DEI conversation, one that truly values and benefits from diversity.

Resources for Black History Month

Tani Brown

Jun 18

Onboarding at Startups

Jun 18

State of the Cloud 2019 · Bessemer Venture Partners

How to build a resilient business with G.R.I.T.

A decade ago there weren’t any private cloud companies valued at $1 billion. Today, there are 55 private cloud unicorns. If we include the additional 44 public cloud companies, there are 99 cloud players valued over $1 billion. What’s truly remarkable about the cloud ecosystem isn’t just the sheer size of the market, but also its interdependence.

When a cloud company scales it often signals the growth of others, but there are a number of other signals to the cloud sector’s velocity. For example, this year, the demand for cloud shares and cloud liquidity hit record highs, outpacing 2015, which was the last record-breaking year.

With IBM’s purchase of Red Hat ($33B), Microsoft’s acquisition of GitHub ($7.5B), and SendGrid joining forces with Twilio ($2.9B), there was more than $90 billion spent in large mergers and acquisitions. More than $50 billion was also added to the market cap through cloud IPOs, including DocuSign, Dropbox, Elastic, and Carbon Black.

For more than a decade, we’ve had the longest bull run in U.S. history. At $175 billion, the top 100 private cloud companies have never been worth more. At this point, many founders are probably wondering how they can protect their companies from volatility.

While uncertain times are still ahead, cloud founders don’t have to thwart their aspirations of growth. Developing a new level of operational rigor by following the G.R.I.T. framework is one way for founders to understand their growth and build an enduring business along the way.

Operate with G.R.I.T.

Operational rigor is what separates early stage companies from the most influential cloud leaders. But take comfort in the fact that it’s possible: Twilio’s Jeff Lawson and Shopify’s Tobias Lütke are just two examples of the many first-time founders who were running cloud businesses during and post-recession.

At Bessemer, we recommend cloud founders operate on G.R.I.T.— a critical set of metrics that resilient, enduring cloud companies use as yardsticks of success.

Growth (ARR)

The first operational metric is annualized recurring revenue (ARR) growth. While companies such as Slack, Twilio, Shopify, and more are all considered successful in their own right, each one had their own path to earning its first $100 million in ARR.

Here’s a breakdown on how long it took for companies to go from $1 million to $100 million AAR:

The top 25 percentile of public cloud companies spends 5.3 years on average to reach the $100 million milestone.
The median 50 percentile spends 7.3 years to reach $100 million in ARR.
The bottom 25 percentile spends 10.6 years to reach $100 million in ARR.

If you want to build the next big cloud company, here’s our Good, Better, Best framework for ARR. A cloud founder should aim for one of these timeframes:

Good: Cloud companies operating on “good” ARR growth models earn the first $10 million in four years, and reach $100 million ARR in ten years. (e.g. Cornerstone On Demand)
Better: Those that are better positioned earn the first $10 million ARR in three years, and reach $100 million ARR in seven years. (e.g. Shopify)
Best: The best performing cloud companies reach $10 million ARR in two years and reach $100 million ARR in five years. (e.g. Twilio, ServiceNow)

Enduring companies don’t just have contingency plans for when a recession hits. They set these goals and figure out how to achieve them based on the expectation that there will eventually be changes in the market.

Retention is your best friend

Retention, the amount of revenue accrued over a period of time, including upsells, is one of the most influential levers for cloud and SaaS businesses to pull when growing ARR. Some of the best performing SaaS businesses we’ve seen in the past decade have higher than 100 percent net retention rate because they’ve built a metered business that sells more to a customer as its business scales.

However, retention rates have different meanings depending on customer segments.

Here are the retention benchmarks a cloud company should aim for, by customer segment:

SMB customers that have an average account contract value less than $12K see a gross retention rate between 70-80 percent and net retention rates between 80-100 percent.
Mid-market companies that have an average account contract value between $12-50K should aim for a gross retention rate between 80-90 percent and net retention between 90-120 percent.
Enterprise businesses that have an average account contract value $50K+ should aim for more than a 90 percent gross retention rate and more than 100 percent net retention.

If a company’s retention rate doesn’t fit within these bands, it’s time to investigate the culprit behind the “leaky bucket.” Churn is always a symptom of larger problems. By identifying and addressing the root cause of churn, a company can directly impact top line ARR growth by just retaining its current book of business.

In the bank

For early-stage cloud founders, the cash you have in the bank reigns Queen (or King). Also known as “runway,” cash is the fuel to build your product, acquire new customers, hire employees, and invest in growth opportunities.

Efficiently managing runway is the lifeblood of an early-stage company’s longevity, and it begins with three critical rules:

Buffer your budgets for a contingency plan;
Target for 18-24 months of runway, at a minimum;
Be as judicious as possible when expanding your team.

Hiring is an effective way to grow a business, but it’s also the most expensive. When in doubt, hire slow and release fast when a new team member cannot drive forward the company’s goals. The way cloud founders allocate their runway will ultimately determine their destination.

Targeted spend

Cloud founders must always spend wisely to fuel growth. In 2017, Bessemer created a way to measure wise spending by coining the Bessemer Efficiency Score, which is defined in two ways, depending on the size of the company.

For startups earning less than $30 million ARR, the efficiency score is defined by net new ARR over net burn. In the Good, Better, Best framework when evaluating efficiency, the “best” score for a company at this stage is greater than 1.5x.

This metric is different than ARR growth because it measures a company’s spending habits. It’s great if a company grows 3x, but if it’s spending crazy amounts to get there, this rate wouldn’t be considered efficient growth.

In a bull market, startups can get away with less efficient growth by acquiring new customers at a higher cost than necessary. However, this approach reflects a lack of discipline and doesn’t make for resilient companies. The good news is that when you do develop more efficient businesses, they are rewarded in all markets.

How to calculate your score

The G.R.I.T. framework highlights critical metrics when evaluating resiliency. By tracking ARR growth, retention, years of runway, and efficiency, the G.R.I.T. framework also translates into an equation.

Here we illustrate how to turn each metric into a variable and calculate a company’s G.R.I.T. score.

Based on Bessemer’s research and the most resilient companies in the industry, we provide another Good, Better, Best benchmark so any cloud founder can see where they fall and how they can improve overtime.

What’s your G.R.I.T. score? Once a cloud founder equates where they land within this framework, they’ll have a clearer idea of where their business can improve, or if it’s time to celebrate (and maintain) a high G.R.I.T. score.

30,000-ft view of The Cloud

Since Bessemer penned the canonical laws of cloud computing more than ten years ago, our investors continue to explore how cloud businesses evolve over time and how these ten laws have aged with time. G.R.I.T. is a new framework for founders to build an enduring cloud business.

A few short years ago, we predicted that the public cloud market would reach $500 billion by 2020. We were happily proven wrong when we hit the mark two years earlier in March of 2018.

Less than a year later, the total cloud market cap sits right around $690 billion. Now, it’s time to set our sights on the next major milestone for the cloud industry, and see how new companies will innovate with emerging technologies.

2019 predictions

Every year at Bessemer, we share our top cloud predictions, which we believe will impact how enduring companies change the way we live, work, and engage with software.

1. Robots to the rescue

We see “robots” as the change agents of the world. Machine learning and artificial intelligence will be instrumental technology for all the apps, platforms, and services cloud founders are building, particularly in industries where people deal with massive amounts of data like healthcare and agriculture.

Robots are especially exciting when they free up human time to work on value-based thinking rather than automated tasks. We see this particularly in business areas like fraud, customer support, and accounting, with companies, such as ScaleFactor or Ada Support.

2. Product has purse strings

Product is foundational to any software company– it’s what you build and sell. However, in the past, product teams were not the traditional, target decision-makers and buyers when businesses evaluated software purchases. They had unlimited budget for headcount, but not software. We think this may have been shortsighted.

If product is the center of the organization and touches all areas of the company (sales, marketing, engineering, and customers), there should be platforms that help people manage, measure, and build the designs, plans, and roadmaps behind products.

We’ve seen entrepreneurs realize this gap and build exciting tools, like Gainsight. There are many more solutions to come since product-centricity gives teams a deeper understanding of every aspect of the software, customer lifecycle, and business.

3. Open source makes money

Open source communities have always been beloved in the Valley – they are tight-knit, full of brilliant engineers, and at the cutting edge of innovation. But in the past, finding commercialization or liquidity has been a challenge. In 2018, there were two record-breaking IPOs for the open source community with Elastic and Pivotal.

We also had three of the largest M&As in history with Red Hat at $33 billion, MuleSoft, and GitHub. Private companies like npm, Confluent, and Hashicorp are developing and innovating open source for the enterprise.

4. Deeper verticalization of mobile

We thought the mobile channel would manifest across both horizontal and vertical sectors, but on further reflection, mobile development is progressing rapidly in vertical sectors like construction, HVAC, etc.

ServiceTitan, for example, offers software and mobile solutions for businesses in field services, and their technicians.

Just think about people you know and how they work. There will certainly be more deskless workers who are always on the move and need access to technology, so we expect to see significant change in the vertical category.

Technical roles such as product, data science, SREs, QA, and others within an organization are prime, underserved buyers. As every company becomes a software company, these technical roles will have growing budgets and purchasing power to make decisions about what types of software they want to use to help them do their jobs better.

PagerDuty, for instance, makes the lives of IT Ops and SRE teams much simpler by providing a reliable alerting system to guarantee alerts are sent when needed.

Periscope Data empowers data analysts to very quickly visualize their SQL queries and create beautiful dashboards.

5. Low code/no code

The Low Code/No Code movement will provide technologies with amazing DX (developer experience) and offload smaller tasks so engineers can focus on more complex problem sets with the help of companies like Twilio and Auth0. No code solutions also give knowledge workers powerful functionality without requiring engineering resources. This includes easy automation, such as Zapier and UiPath, and business apps within the Salesforce and Workday ecosystem.

These are only five of the many trends we’re excited about at Bessemer, and we look forward to seeing how these ideas continue to contribute to the Cloud ecosystem.

Jun 18

Co-founder Conflict

Jun 18

Ask The Entrepreneurs: 16 Ways to Master Your Work-Life Balance as an Entrepreneur

Jun 18

Finding Mentors

Jun 18

How to Hire a Product Manager

Jun 18

50 Questions to Find a Co-Founder and a Startup Idea

Gloria Lin has gone on a lot of dates in the past year. No, not that kind. We’re talking about co-founder dating.

As the first head of product at Flipboard and the first PM hire at Stripe, Lin’s seen founding teams in action — and knew what she was looking for as she set out to build a company of her own. “I always wanted to team up with someone. My experiences as a product leader were strongest when I was partnering closely with an engineering leader,” says Lin. “When I left to start a company, there were a few spaces I was interested in, but I didn’t have a specific startup idea so I set my sights on finding a strong co-founder to work with.”

But she quickly found that was easier said than done. “Most of the co-founder stories I’d heard fell in this bucket of former co-workers pairing up to go after an idea. But it’s not that simple. You have to both want to do a startup — requiring similar levels of high-risk tolerance — and be available at the same time, which depends on life and financial circumstances. And once you step outside of that pool, it gets harder to meet someone,” says Lin. “I knew I didn’t want my search to be random or unfocused, so I honed my process and took my time. I ended up ‘dating’ six different potential co-founders over the course of a year. Just like real-life dating, sometimes it seemed like I was going to end up alone. Eventually, I met Joel Poloney and everything clicked. Now we’re working on a new stealth company together.”

As the next generation of company builders takes shape and new founder mafias spin out of places like Stripe, it stands to reason that more co-founder stories won’t fit the traditional mold, and will instead look a lot more like Lin’s. And judging from threads on Reddit, countless questions on Quora, and all the “first dates” filling up coffee shops in SOMA, the carefully designed hunt for a co-founder is already afoot.

While the Review has covered co-founder considerations before, from getting vulnerable about painful “divorces” to applying a framework for strategically assembling a founding team, we’ve never seen a process like Lin’s. It’s a detailed, step-by-step playbook for thinking through all the potential pitfalls that can ruin even the best of co-founder relationships.

In this exclusive interview, Lin presents that rigorous approach in full, from how she found potential partners and handled early conversations to how they ideated and prototyped together to narrow in on a more specific idea. Whether you’re a proven founder working on your next play or a wannabe entrepreneur waiting in the wings, her process can add a dose of rigor to your own search for a co-founder.

Lin also shares the incredibly detailed co-founder questionnaire — with 50 questions spanning across six categories — that she and other fellow founders have collaborated on to probe compatibility more deeply. We’ll highlight a handful of impactful questions here in this article, tacking on Lin’s marginalia: her reflections on why these questions stood out, the sticking points you need to watch for, and how you’ll know when you’ve found “the one.”

But we've also included the full set (below, in a designed PDF template so you can grab and go, and further down in a Google Doc, in case you'd like to edit and add your own questions).

Want to jump straight into the set of 50 questions to ask a potential co-founder?

BEFORE YOU GET STARTED: COMMON ADVICE WITH SOME CAVEATS

The search for a co-founder often conjures up comparisons to dating. It’s become a well-worn metaphor because from fights to marriage to divorce, parallels abound.

“Finding a co-founder can feel like a more intense version of dating. One key difference though is that most people have at least some experience with real-life dating. And there’s certainly tons of self-help books for tips as well as apps that make it easier to meet people. But when it comes to figuring out how to find a co-founder, it’s hard to know where to begin,” says Lin.

“That’s a huge problem because two of the most common causes of startup failures are not finding product/market fit and co-founder issues. The former is top of mind for every budding entrepreneur, but I don’t think people consider the latter as much when they’re crafting their pitches," she says. "We just finished our fundraising process and I can’t tell you how many seasoned investors told us about how a co-founder situation blew up one of their companies. But even so, there’s not much guidance out there on how to pick the right co-founder.”

One reason for that lack of guidance is that it’s hard to get too prescriptive — after all, folks are approaching the co-founder search and company building process from different places. You could be:

Looking for a co-founder and neither of you have an idea yet.
Searching for a business or technical co-founder to help you execute on an idea you’ve been working on.
Pairing up with someone you already know to find an idea.

“The advice on how to tailor your search depends on what you’re looking for. If you already have a vision for your startup in mind, then you might want to skip straight into getting to know your potential co-founder on a deeper level. If you’re going to work with someone you already know, you may want to spend extra time making sure you’re aligned on how you want to build the company,” says Lin.

“I was in that first bucket. People get hung up on having either a solid company idea or a specific co-founder in place from the start, but I don’t think you need either right away. See the white space as an opportunity to try working together and a chance to explore interesting ideas at the same time.”

When it comes to starting a company, you can figure out the right space to go after and find the right person to tackle it with in parallel. Don’t compromise on either.

Lin came to this realization after seeing the hidden dangers in pairing up quickly with an old friend. “I’ve seen new co-founders get further down the company building path and suddenly realize that, ‘Oh, we didn't ever talk about this,’ or, ‘I didn't realize that we have such opposing views on this topic,’” she says. “It's kind of like moving in with someone for the first time and realizing that they leave their socks on the floor or they don’t share your approach to finances. They have all these habits big and small that suggest you may not be such a great match after all.”

Here, Lin recommends a few additional broad takeaways to keep in mind before kicking off your search:

Take your time — but realize the clock is ticking.

In Lin’s view, one of the biggest mistakes people tend to make is not giving the process time to unfold. “You don’t want to rush into a pairing or stop your search prematurely,” she says. “Alfred Lin once gave me some advice that was clarifying: It’s common practice to take three to six months to hire an executive, so why wouldn't you take the same amount of care to find a co-founder? Because that person is probably going to be around even longer. You’ll potentially work together for a decade or more.”

All too often, people jump into company building opportunities and don’t spend the time testing the depths of the co-founder relationship — which makes for shotgun marriages that carry more risk.

However, there is an important caveat to consider. “People only have a certain amount of financial runway they can survive on while they’re exploring a company. Some people can only go three months, while others could last three years. As you start to run out of resources, it can feel like a very accelerated, which is why you can end up with some shotgun marriages,” she says.

Opposites attract — but don’t dismiss overlap.

“People who are very similar in their strengths can lead to weaker co-founding situations. You want someone who shares similar values, but in terms of interests or characteristics, it’s often better if you’re different — there’s a reason they say opposites attract,” says Lin. “As a small example, my co-founder Joel and I don't share a lot of personal tastes in music and other areas that are more subjective, but we’re so aligned on how we think about company building.”

We naturally flock to folks with similar experiences, tastes, and skills, but entrepreneurs overlook founding team diversity at their own peril — it’s a huge source of strength.

However, this advice doesn’t always map onto previous experiences quite so neatly. “You can’t just glance at a resume and pass on all the ones that are too similar to yours,” says Lin. “Sometimes two people with the same background want very different things when it comes to building a startup. If they’re both PMs, one might want to focus on product, while the other person may want to stretch and get into the business side. It's highly dependent on what they want to do, not just what they've done before — you have to talk about it to find out.”

DECONSTRUCTING THE PROCESS

With that high-level advice to set the scene, let’s dig into Lin’s process — and why she recommends following one in the first place. “You need to be really intentional about how you spend your time together,” she says. “In my experience a ‘Let’s see what happens’ approach with meandering conversations and unstructured brainstorming is not as effective.”

Still, a positive outcome is anything but guaranteed and progress is often hard to sense. “Building a startup feels like you’re standing at the start of a maze and you don’t know where the path is going to lead you,” says Lin. “It can be frustrating because you have no idea if jamming really hard for a week will get you any closer to your goal. You don’t know if it's a dead-end. You need to put one foot in front of the other — you have to keep moving.”

And she’s found that you can cover more ground faster than you might think. “You can get a lot of data on what it would be like to be someone’s co-founder in a few weeks. I don't think that these steps are strictly linear — there's no waterfall chart that perfectly illustrates the stages as you move through them. But generally speaking, here’s the process I followed in a nutshell:

Step 1: Find potential co-founders from your network of entrepreneurial communities.
Step 2: Identify overlap through initial conversations. Have a few coffee chats to cover some basic topics such as: What’s your story? What sectors or industries do you have experience in? What areas are you interested in building a startup in?
Step 3: Dive into exploring specific ideas with brainstorming and lightweight prototyping. The goal is to both make progress toward an idea and gain collaboration experience to see what it would be like to work together.
Step 4: Fill out the co-founder questionnaire separately and schedule three to four working sessions to go over your respective answers.
Step 5: Commit to working together or part ways. Know when to pull the trigger — and when to stop and start anew with someone else.

“The shortest round I had ended after just a couple of those initial coffee chats. It was somebody who seemed great on paper, but we didn’t mesh in real life,” says Lin. “In contrast, I spent four months working with my current co-founder to validate that we were on the right track before we committed.”

In the sections that follow, Lin gets granular on each of those high-level steps, filling in tactical advice and drawing on stories from her own co-founder search experiences.

STEP 1: FIND POTENTIAL CO-FOUNDERS TO FILL YOUR PIPELINE

“‘Where do I find people?’ is one of the biggest questions I get when people ask me for advice. There isn’t a ‘Tinder for co-founders’ app that everyone is on. Sourcing is hard,” says Lin. “There were times in my process where I flipped back to working on an idea on my own because I didn’t have another potential co-founder lined up.”

Lin typically courted a mix of folks that she had either known for a long time, gotten introduced by a mutual friend, or just recently met at an event. “One person was a classmate from college whom I hadn't spoken with in a while. Some were folks that I’d met through the broader entrepreneurial communities I’m a part of, like South Park Commons,” she says.

“I tried to engineer serendipity — I wasn't heads down hoping for someone to cross my path. I told all my friends and closer connections that I was looking for co-founders and asked for recommendations and intros. I think you have to get out of your comfort zone and try to make more connections that count,” says Lin. “More tactically, joining entrepreneurial communities and attending events are great ways to broaden your pool. There are even some early-stage investors who help facilitate some of those interactions. The long and the short of it is that you have to be open to opportunity.”

The only opportunity that should give you pause is a chance to work with a particularly close friend. “I wouldn't go as far as saying, ‘Don't go fish in that pond,’ but you need to go into it eyes wide open,” says Lin. “Noam Wasserman literally wrote the book on this — in The Founder’s Dilemmas, he explored what kind of founders are more successful than others. His research found that social connections are likely to be stable in the first six months — the honeymoon period — but become riskier over time. And even if it works out smoothly, doing a startup together will surely affect your friendship, so you have to be prepared for that.”

STEP 2: IDENTIFY AREAS OF OVERLAP TO SURFACE A QUICK NO

After finding a potential lead, schedule a few coffee chats or calls to uncover common ground — or a lack thereof. “This stage is very exploratory. Nothing’s set in stone. You’re looking for signals that it makes sense to move forward and invest more of your time,” says Lin.

In particular, she searches for a lack of alignment in this step. “Actively look for counterfactuals, the places where you say ‘Oh, I actually don't think we're aligned on this point.’ I had a great initial chat with one person, but we found that one of us wanted to bootstrap our company while the other wanted to raise as much money as possible. It probably wasn’t a fit, so we didn’t need to keep spinning our wheels,” says Lin.

Here are the threads she recommends pulling on in these early conversations:

Areas of interest: What kinds of things are you excited to work on? What have you explored recently? Are we interested in the same industries and business models? “Of course, your idea can change completely. Co-founding pairs pivot all the time, but you often move into an adjacent space, so it’s helpful to get a mapping of what you're respectively interested in,” says Lin. “With each of the six potential co-founders I dated, I explored different areas: identity, recruiting, interior design, security, crypto. What’s interesting is that some ideas morph and take on a totally different direction, while others don’t work out with one person, but end up making sense with someone else later. For example, I’d previously explored interior design with someone else, but now my co-founder and I are building something in the adjacent construction space.”
Broad roles: Are we interested in potentially exploring a co-founder relationship together? What would that look like? “This isn’t a negotiation over who wants to be the CEO. It’s more of a ‘In an ideal world, what are you imagining?’ kind of discussion,” she says. “There's a rough sense of roles but it's not super clear cut. It’s more like ‘I could focus on product and marketing and you could work on the tech and operations.’”

STEP 3: SPEND TWO WEEKS PROTOTYPING TO SEE IF AN IDEA HAS LEGS

After spot checking for initial alignment, Lin dives straight into tackling a project with a potential co-founder. “The first or second coffee chat may not tell you that much. But once you start doing some kind of project, you get so much more data on the person and their work style,” she says.

“For me, this was the fun part. It’s about getting your hands dirty, digging into a space, figuring out the need, and seeing if a startup idea has potential,” says Lin. “It’s also an opportunity to uncover if you’re actually interested in a certain area. A few times I thought I was passionate about a certain industry, only to discover through hands-on projects that I actually didn’t enjoy it.”

It’s not about tinkering aimlessly, though. Lin suggests timeboxing this exploratory period to about two weeks to maximize both learning fast and moving quickly. She’s also looked to other frameworks for guidance. “I was inspired by Nat Turner’s approach to finding a startup idea,” says Lin. “He and his co-founder refined them so successfully — and quickly — that they were able to start a company in healthcare without domain expertise. I had their process in mind each time I was ideating.”

Gloria Lin and her co-founder, Joel Poloney

Here’s an overview of targeted tactics to use when exploring an idea with a potential co-founder, the very same ones Lin used to test six different startup ideas of her own:

Explore consumer and enterprise startup ideas differently.

When investigating a consumer play with a potential co-founder, Lin is a firm believer that you have to try to build something. “It doesn't mean that you have to build a full production-ready app. Figure out the cheapest possible thing, the crappiest MVP you can get out there within a week or two just to see how things go,” says Lin. “That could be a really janky prototype, a small Chrome extension, or a landing page. Anything where you can put it out into the world and see if there’s a response.”

Contrast that with enterprise, which is more about customer discovery. “With enterprise, building often isn’t the hard part. It’s all about selling. You need a shortcut to figure out, ‘Am I making something people want?’ Do a bunch of interviews with experts or potential customers to find out. Customers will tell you what their problems are. If you listen very carefully, you might be able to figure out a jumping off point to build a company around.”

When you’re exploring enterprise startup ideas, you have to get out and talk to customers. My co-founder and I got ideas from those conversations that I could have never come up with on my own in a million years.

Here’s a sampling of the specific questions Lin and her potential co-founders asked in these customer calls:

How do you currently manage this process?
How big of a pain point is it for you, compared to other pain points you have?
If you could wave a magic wand and have that problem go away, how would that affect your work or your customers?

Use these clues to find out if you’re onto something.

Of course, with time constraints and minimal resources, you can’t expect statistically significant insights from this discovery stage work. That said, there are indicators that you may be on the right track.

“On the consumer side, a good signal is if some people tell you they want it, if you see others actually using it and maybe even actively badgering you for more. Segment is a great example of this. They launched an open source analytics library with a landing page and it blew up on Hacker News,” says Lin. “With enterprise, it’s about looking for patterns. You need some minimum number of people in a segment saying, ‘Yes, I want this, I’d pay you for this and here’s how much I'd pay.”

Get ready for the dropoff.

“This ideation stage was where most of my ‘breakups’ happened,” says Lin. “It’s a good litmus test for whether the partnership can work. Obviously, a lot of ideas you generate together aren’t going to work out. With the right person, you can push through that, and move onto other areas and experiments. But sometimes when ideas die on the vine, the partnership can lose steam. You start to question if this person is the right partner for you. Other times, a business idea had true potential, but we discovered that we had incompatible working styles.”

In Lin’s experience, these break-up conversations can be handled several different ways. “I was ghosted once,” she laughs. “With others, we had in-person convos or phone calls. There are lots of ways people can decide not to work together, but for me personally, I most appreciated when there was a clear go or no-go date, and we had one or two direct conversations about the viability of us working together. Those are the relationships I feel better about today.”

Have the courage to talk about these potential partnerships directly, especially when it's not a fit.

STEP 4: BRING ON THE QUESTIONNAIRE

Once you have a very basic sense of how prototyping is going, the next step is to tackle the finer points of what the co-founder relationship might look like. Enter the co-founder questionnaire, the getting-to-know-you gauntlet that Lin throws down before seriously considering starting a company with someone.

Here’s the Google Doc version of the questionnaire if you’d like to edit and add in questions of your own. Want to grab the list Lin used and go? Below you’ll find a handy template, designed to make it easy for you to quickly share with a fellow founder you’re considering teaming up with:

As with most things in life, timing is everything. “Some folks are open books and they’ll do it immediately, but for others, getting into this stuff seems way too personal,” says Lin. “Out of the fellow founders I’ve known who’ve used the questionnaire, they’ve all brought it in at different times based on what they were looking for in a partner.”

If you’re looking for a co-founder and an idea in parallel, you might want to use the questionnaire before you get into prototyping. “One pair I know wanted to understand each other better before investing time in ideation and business development,” says Lin.
If you’re searching for a business or technical counterpart to help you execute on a game plan, you may want to use the questionnaire earlier in the process. “One founder I knew used it before his second coffee chat. That way you can quickly screen out people who won't be a fit, given the specificity of what you know you’re looking for,” says Lin.
If you’re pairing up with someone you already know, there’s still tremendous value in running through the questions before taking the leap. “People can behave quite differently in different settings. Working at a company alongside someone is very different than co-founding a new startup together. Founder life can be much more stressful,” says Lin.

Here’s Lin’s own take: “I did after we had a viable idea in sight. I’d pull the questionnaire out of the toolkit when you have an inkling that things might get serious. Just like in dating, there’s an appropriate time to start tackling some tough questions: Do you want kids? Could you see yourself getting married? What’s your approach to personal finances? If you ask these on the first date, you might seem too intense. But if you date for years before ever bringing them up, that’s probably not ideal either. It’s about finding the approach that works for you and what you’re looking for in a co-founder.”

Here, she gives a tactical overview of how the questions evolved and how co-founding pairs can put them to work:

The making of the questions:

This specific questionnaire for co-founders has been quietly making the rounds in certain entrepreneurial circles for some time. “It originated with Paul Biggar. He forwarded me some questions he’d been asking of potential co-founders," says Lin. "I thought it was a really clarifying and helpful tool, so I baked it into my process going forward.”

Lin then expanded on that question set to make it even more robust and pull out what she was interested in learning. “At one point, I turned it into the co-founder’s version of The 36 Questions That Lead to Love, really leaning into the dating angle,” she laughs. “But the Google Doc we have going now has expanded and evolved significantly from that original set. It’s been fun to see others add to it over time, and I certainly can’t take most of the credit for it. Evan Beard, Nick Lane-Smith, Chloe Sladden, Ramesh Balakrishnan, and Ellen Pao in particular added so many great questions. And it will continue to evolve as entrepreneurs take the doc, and add or subtract questions as they figure out what works for them.”

Lin found the questionnaire to be a valuable tool as she was looking for a fellow company builder. But if you’re still not convinced that you should fold it into your own process, here’s a list of quick hits on why this set of questions is worth your while:

It makes sure you’re aligned on values: “There are lots of different, perfectly valid ways to build a company, but the co-founders need to be as aligned as possible. The questions surface the motivations and preferences that will factor in as you come up with company values and try to scale culture when hiring,” says Lin. “You run into a lot of philosophical disagreements than can spiral into massive fallouts later on, so it’s good to find out before you’re in too deep.”
It helps you flex the vulnerability muscle: “In sharing your answers to the questions, you have a tool that allows you to say: ‘This is what I’m like at my best and my worst. This is how I react when I get stressed. Here’s how I can prevent burnout and achieve my ideal lifestyle. Here are my hopes and dreams,’” says Lin. “Opening up like that with someone you don’t know very well can be hard, but I’m convinced many co-founding pairs fall apart partially because they didn’t understand each other’s motivations and fears at a deep level. Vulnerability is the key ingredient in any strong co-founder relationship, but it doesn’t come naturally — you have to work at it. And while it does take time, there are ways to build trust quickly, and I’ve found this questionnaire to be one of them.”
It highlights gaps on the founding team: “Many of the questions center around your strengths and weaknesses, both professional and personal. I found that this process uncovered our weak spots as a collective. This can be useful for both hiring and for identifying your own areas of growth,” says Lin. “For Joel and I, we're building an enterprise startup, and like many founders, neither of us has first hand sales experience.”

Advice before you dive in:

Lin notes that while you can run through the questionnaire several different ways, there are some essential elements to keep in mind:

Custom-tailor your own test. “The questionnaire process is very flexible,” says Lin. “Pick your own order with your potential co-founder to ease into the more intense questions. Pare it down for a lightweight version at co-founder speed dating events. Add more questions of your own to target what you’re uniquely looking for.”
Keep your eyes on your own paper. “In my experience, filling it out for the first time usually takes about two to three hours if you’re being thoughtful. It’s important to do it independently as opposed to running through them together live. Don’t get stuck in groupthink — you need to surface true differences,” says Lin.
Reconvene to go over your respective answers. “You could just share your answers over email, but I think you’d miss some context and nuance. If you discuss the answers in person, that can take at least six to 10 hours. I’d never recommend going over all the answers in one marathon session — that's too intense,” says Lin. “Since the questions are already broken up into sections, we typically covered a section or two in one sitting, with about three to five sessions total to go over everything. You could spend a few days on this part. One founder estimated that she spent at least 60 hours on it over a four week period.”

A natural question comes up as founding pairs run through the questionnaire: How much alignment do you need in your answers? “Do you have to be 100% aligned on everything or is 75% okay? At the end of the day you need to rely on your experience and your intuition,” says Lin, “Make a checklist of your non-negotiables, but keep it small — don’t have more than three.”

When it comes to finding alignment with a potential co-founder, your list of non-negotiables better be really small — otherwise it doesn’t mean much.

When you decide to build a company with someone, you’re giving up total control — it won’t be done exactly the way you would have if you were on your own. “You need to figure out the difference between the compromises that will keep you up at night and the areas where you can stretch to accommodate a different perspective,” says Lin.

When identifying potential spots for compromise, she’s found it helpful to think about it in terms of table-stakes, must-haves, and flex areas:

Table-stakes: “These are the givens, the absolute basics. As a product leader, I had to have someone with a technical background to build the thing. Otherwise it wouldn’t be a very good tech company. So the technical folks who had ambitions to step out of the codebase and pivot into the business side of things weren’t as good of a fit for me,” says Lin.
Must-haves: “I had two: One was personal maturity. The second litmus test I always had in the back of my mind was: When I'm not in the room am I going to agree with their judgment calls? Would I trust this person in their hiring and firing decisions? Could this person oversee an important function for the company, whether it's lawyers or finances? I wanted to be able to fully hand off an aspect of the company to someone and depend on their judgment,” she says.
Flex areas: “For example, some folks aren’t natural-born communicators. Or perhaps you’re looking for a technical co-founder to help build and recruit, but they don’t have a ton of experience as a manager,” says Lin. “These factors might give you pause, but they don’t have to be deal-breakers. If they exhibit humility, a willingness to learn and self-awareness around these areas of growth, you can still make a great team.”

The deep-dive into the questions:

Lin shared her co-founder questionnaire with the Review in full so others could get a clear sense of the template and level of granularity that’s worked for her and others in the co-founder search. As it stands, the questionnaire contains 50 questions, too many to cover in full here.

We’ve thus separated her guide into sections and highlighted a handful of standout questions, after which we’ve included her commentary on why they matter and what to look for:

Part 0. How You Operate

“Part 0 is mostly in the terrain of behavioral interviews. You’re looking to learn more about the person’s values, how they work, where they spike, and their shortcomings. How would they be an asset to your team and where would you have to help them out? How self-aware do they seem? How vulnerable do they get?” says Lin.

What’s the worst interpersonal conflict you’ve dealt with? How did you handle it? “I think this question is particularly important to look out for. I want to have the tools I need to navigate inevitable conflicts successfully with my co-founder,” says Lin.
How many hours/week are you willing to work? What sounds ideal and what sounds like hell? “If one person says ‘I really love grinding out, I thrived with investment banking hours,’ and the other person says, ‘I work very hard, but I’m not going to exceed 50 hours a week,’ that clearly sets you up for a collision,” says Lin. “This is also important because it impacts the tone you set for the rest of the company.”

Part I. Roles

How do you see your role changing after we reach product/market fit? What about once we start to scale? “It’s important to break out how your role as co-founder will change, especially when you have multiple co-founders,” says Lin. “What you take on before you hit product/market fit versus afterwards can change pretty drastically and you need to temper expectations. You might start off leading sales but then quickly have to give away your Legos to someone else — I was looking for people who were very comfortable with that.”
Areas of Responsibility Exercise: “I found this exercise to be so useful. There are a lot of areas that neither of you have experience in, so adding the dimension of who has high passion for it can be really helpful,” says Lin. Here’s how it works: Rank yourself in the areas below (both as an individual contributor and as a leader) on a scale of 1-10. Then rate your passion in each of the areas on a scale of none to high (e.g. “I'm an 8 in sales, but hate it now”). Cluster AORs based on rank and discuss how they could be assigned to individuals. (E.g. John is a 10 in product, so he gets that AOR). Break ties using the passion rating. (E.g. Nick is a 7 in sales with medium passion and Gloria is a 7 in Sales with high passion, so Gloria will take on sales). Do these clusters align with everyone’s expectations, skills, and desires? Do we all agree on the areas of responsibility for the CEO, CTO, and COO?

Part II. Corporate Structure and Funding

“The bigger points of division in this section have typically been around fundraising, exits, and equity, all of the stuff that can turn into boardroom battles,” says Lin. “My goal is always to at least talk about governance and logistics at a high-level. Most co-founders aren’t lawyers and haven't thought through the nuts and bolts of corporate structure. You don’t have to have perfect answers here, but make sure you think about it proactively and discuss it intentionally — too often it’s something that evolves haphazardly, which is a recipe for hurt feelings later on.”

How much money should we raise? In the range of “bootstrapped small business” to “go big or go home,” where do you want this startup to go? “This can be a huge sticking point. People often disagree about how big they want the company to get, or how quickly they want to burn. You could want to ‘go big or go home,’ take VC dollars but grow more sustainably, or be bootstrapped and very frugal,” says Lin. “This is important when you’re strategizing about follow-on funding.”
How should founder equity be set? What’s your philosophy on the employee equity pool? “Equity always ends up being a natural friction point. It’s about power, sharing it, and the sort of team you hope to build with your co-founder. I intentionally looked for equal or nearly equal partnership setups, but I’ve heard other founders say they were advised not to seek out an equal partnership,” says Lin. “Sometimes a highly unequal arrangement makes sense when there’s a mismatch in experience between the co-founders.”
What do we do if we find product/market fit, yet none of the founders are excited about that product? “This happened to a founder I know,” says Lin. “They ended up selling the company after the company found product/market fit because it didn’t spark joy. It may seem like an edge case, but I think this one is important because it speaks to what you value and the importance of passion.”

Part III. Personal Motivation

Why do you want to start a company — in general, and in particular right now? “Here was my answer: I'm a product person. I love to see things out in the world, to think about futures that are about five to ten years away from mass adoption and work to bring them closer to our reach,” says Lin.
What makes you gritty? “This is one of my favorites. It can be tough to answer, but you're looking for examples and stories, and the thinking behind them,” says Lin. “For example, I talk about two of my traits and provide stories to back them up. I’m very strategic about which opportunities I go after, but I’m relentless once I decide to pursue them. And there are a few areas where I'm stubborn as a mule.”
How important is diversity & inclusion? Concretely, how would you put that into action? “You could tell who had concrete ideas about how to create a diverse and inclusive environment and who said they cared but hadn't put in as much thought yet. The ones with more tangible suggestions obviously signaled they took it more seriously,” says Lin.

Part VI. Co-Founder Relationship

In case this becomes part of our partnership’s evolution, how would you go about handling a startup divorce? How would you think about bringing on a third (or N+1) cofounder? “There's no right answer to either of these questions, but I looked for maturity in thinking about how to handle these thorny issues,” says Lin.

STEP 5: COMMIT AND STAY THE COURSE

The last and final stop on the co-founder search journey is deciding to make it official. “There’s a bit of an optimal stopping problem here. Are you committing too soon? Will someone better come along? There’s a math-based rule of thumb for real-life dating, but it doesn’t map so cleanly onto selecting a co-founder,” says Lin. “When it comes to founding a company, your personal runway is the stopping point. I’ve seen friends say ‘This is the last person I co-founder date with before I have to go find a job.’”

But those considerations aside, it can be hard to know when to pull the trigger, especially early on in your process. “For those like me who are very hungry for information, you have a temptation to try and get even more data. But you reach a point when there’s nothing more to collect — you have to take a leap of faith.”

In Lin’s experience, she knew she’d found “the one” after comparing notes on the co-founder questionnaire. “Joel and I wrote all of our answers in our notebook separately and then came back to compare — and 95% of our answers were the same,” she says. “Of course, this was after we spent four months working together. We’d already uncovered a really interesting market opportunity. All of this put together made me feel ready to dive in.”

Now in the thick of their company-building journey, Lin and her co-founder are focused on getting their idea off the ground. But they still plan on making the co-founder relationship a true priority. “If you spend so much time making this monumental decision, then you need to put work into your relationship over time. It’s easy to get caught up in the stress of startup life and de-prioritize it, but just because you were on the same page at the outset doesn’t mean you will continue to be without intentional effort,” says Lin.

“I’m sure our relationship will be seriously tested as we walk further down the company building path together. But I think you know that you have something special on your hands when you have an easy chemistry and you’re both willing to put in the commitment required for the long haul. It might take you quite a bit of time to find the right co-founder, but when you find that person, you’ll be glad that you waited. After all, the real work is just beginning.”

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A Manager's Guide to The 4 Habits of Inclusive Leadership | First Round Review

“Right now, leaders and managers across tech are scrambling to figure out how to respond to the Black Lives Matter movement and learn more about how they can be anti-racist. From revisiting hiring practices to organizing internal conversations about race and allyship, there’s now a pressure to act quickly in an industry that’s thus far moved pretty slowly when it comes to investing in inclusion,” says Vanessa Tanicien.

Tanicien is well suited to help companies that are ready to tackle this work. As a leadership trainer and facilitator at LifeLabs Learning, she and her colleagues partner with 700+ companies like Slack, Peloton and Warby Parker to deliver research-driven programs that train managers and teams on how to master the most essential leadership skills and habits in the shortest time.

“At LifeLabs, we’re focused on the smallest changes that have the biggest impact,” she says. “To be clear, there are critical systems-level changes needed to combat bias and racism in everything from education and product building to hiring and performance reviews. But in addition, leaders also have the opportunity to be anti-racist and inclusive in their daily interactions — something that can help keep this work centered and sustained.”

Along with fellow leadership trainer Massella Dukuly, LifeLabs co-CEO Tania Luna, facilitation lead Dr. Vaneeta Sandhu and Tanicien (virtually) stopped by the First Round community recently for a tactical discussion on why and how leaders can become more deliberately inclusive. Given the much-needed push for change that has been taking place in the tech industry, we thought we’d share our notes from this internal conversation with a wider audience here on the Review. (Fair warning, we took lots of notes.)

From the immediate need to hold space for Black employees right now and lead vulnerable discussions with your team, to the long-term behaviors that build a welcoming culture, the team at LifeLabs distills inclusive leadership into its four most essential habits. For each of these high-impact behaviors, Dukuly, Luna, Sandhu and Tanicien share the small tactics and key questions that improve interactions and decisions. Their advice serves as an excellent starting point for leaders who have a renewed motivation to show up and work toward enduring change — the kind that starts within.

WHY THE “I” IN DEI MATTERS AND WHAT IT ACTUALLY MEANS:

When it comes to Diversity, Equity, and Inclusion (DEI) strategies, companies tend to concentrate their energy on hiring and sharing reports about “diversity data” instead of examining the existing dynamics within their own walls. Since the former deals in numbers, and the latter involves squisher concepts like belonging, the “I” in the acronym is too often left out.

And that has a real impact on everything from performance to retention. “As humans, our brains are wired for bias. This means that we have to be intentional and systematic about welcoming diversity and establishing equity and inclusion,” says trainer Massella Dukuly. “You can’t just assume inclusion will sprout organically once you’ve introduced more diversity.”

To get started on that work, Co-CEO Tania Luna emphasizes that it’s important to first redefine leadership. “Leadership isn’t saying, ‘Follow me. I'll take you somewhere.’ It's about what happens when I leave. Are you even more effective than you were before? Are people bringing out the best in one another? Generally, what we see in research is when groups of people work together, we all start putting in less effort — an effect first discovered by psychologist Max Ringelmann,” she says.

“Great leadership is about catalyzing more effort, engagement and productivity. It’s creating a formula where 1+1 = 3. In many ways, this happens as a result of typically small, invisible acts of inclusion — giving credit for work, asking to hear other perspectives, or simply following up to say thank you,” Luna continues. “But focusing on the small things is quite unnatural for us. Sure, inclusion can also look like wearing or posting symbols of allyship and publicly stating your commitment to using your privilege to support others, but meaningful inclusion is about those everyday actions that most of us don’t even notice.”

Here’s a simple definition: Inclusive leaders leave every person and every room better than they found it.

When facilitating workshops, Vanessa Tanicien also finds it’s helpful to highlight the opposite of inclusion so we can learn by contrast. “We humans default to, ‘Who do I trust here?’ or ‘Who do I have a good relationship with?’ or ‘Who am I sitting next to?’ and then pull those people into rooms for conversations to solve problems or share info. All these tiny micro exclusions add up without us even realizing,” she says. “This tendency to lean on the people we already know and like is amplified in the remote space where spontaneous collisions are less frequent.”

In contrast, inclusion is about bringing others into the fold. “It’s about sourcing the thoughts and feelings of others so we can come up with solutions that benefit the whole. It requires extra intention to empower the people around you and give everyone equal access to those opportunities for growth and contribution,” says Tanicien.

To unpack how managers can incorporate these principles of inclusive leadership more practically, the LifeLabs group breaks it down into these four habits:

“Handling difficult conversations with care and authenticity is most top of mind right now, so we’ll dive into that first. But while this might be the pressing work in the near-term, the other three habits are absolutely crucial for sustaining change and getting out of our pattern of reacting in the short-term and easing up as more days and weeks go by,” says Luna.

INCLUSIVE LEADERSHIP HABIT #1: INVITE AND DISPLAY AUTHENTICITY:

One of the most pressing responsibilities of leaders right now is to make it safe for employees to speak up about their unique needs and experiences. But that’s easier said than done.

“We often hear these slogans in the workplace, like ‘Come as you are,’ or ‘Bring your whole self.’ But the point of those messages shouldn’t just be about wearing a wacky outfit to the office and everyone being cool with it,” says Luna. “More concretely, it’s about the ability to give upward feedback, ask for what you need, admit mistakes and reveal aspects of who you are that don’t fit the dominant culture — without getting punished. For example many Black people today are still told that wearing their hair naturally is ‘unprofessional.’”

In many workplaces, conforming is a survival tactic. “The choice becomes: fit in or deal with having fewer opportunities for growth, connection and contribution, and perhaps even risk your job security. Research by Claude Steele and many others has revealed that this pressure to conform is heaviest on individuals from marginalized groups, leading to chronic stress, disengagement and a loss of productivity,” says Luna. “In short, when people do not feel safe enough to bring their real selves to work, the entire company loses out.”

Vanessa Tanicien, Leadership Trainer and Facilitator at LifeLabs Learning

Tanicien digs into the very personal underside of not showing up authentically: “Somewhere along the way, people decided that there's a certain way to be and act in order to be liked at the office. Unfortunately, people-pleasing is one of the deepest forms of manipulation that exists. You’re essentially figuring out how to get people to like you in a way that's disingenuous to yourself, creating distance between ‘work you’ and the person that you see yourself to be. That’s why I decided a long time ago that I wasn't going to wear this mask to work.”

Tanicien also notes that as we adapt to working remotely, our ability to keep up this charade is now more challenging than ever. “This is due to something called integration versus segmentation. Your identities were previously physically segmented. You used to leave your house, walk to the train or get in your car and then arrive at the office and suddenly you’re ‘work you.’ Then you got off work and went back to ‘home you.’ Those lines are now blurred,” she says.

“So keeping up those emotional barriers is much harder. It takes a lot of mental energy to maintain that divide when there are no more cues to let the brain know that it's in one place versus another. This new level of integration pushes people to be more real and show up in ways they haven’t before. As a leader, you have to be prepared for that. It’s your opportunity to show that people’s real selves are welcome here. Not only will inviting authenticity increase engagement, it will also allow you to meet people’s real needs.”

The silver lining to this environment we’re all sharing right now is that people are forced to vulnerably connect and actually have real conversations — we have nowhere to hide, folks.

With that context in mind, the LifeLabs team outlines three specific suggestions for how leaders can meet this moment by both displaying and inviting authenticity:

1. Check in before checking on.

Many might be feeling an impulse to check on the Black people in their lives and ask how they’re doing. But you’ve also probably seen articles and helpful Instagram posts that flag why this may not be a one-size-fits-all solution.

“As a Black woman in America, I have gotten a lot of those texts. And some of them were more well received than others. I’m definitely not speaking for all Black Americans here, but this is how I’d explain what makes the good messages different: They come from an authentic place,” says Tanicien. “They come from people you've already been talking to, or who you already have relationships with. Otherwise, it can seem a bit see-through or ego-driven.”

Massella Dukuly, Leadership Trainer at LifeLabs Learning

Dukuly (who is also a Black woman) added on: “From my perspective, I still want to be your friend. I don't want you to start treating me differently or want you to feel that we need to have this weird interaction,” she says. “I want depth to these conversations, and that depth should be proportionate to the already-existent relationship. ‘I'm here if you'd like to talk,’ only works if in fact we have previously truly talked. If you’re a former co-worker I haven’t spoken to in three years, do you actually want me to call you up and start talking about systematic oppression? Probably not.”

When studying what makes great managers different, the LifeLabs team’s research shows there’s a big difference between leading questions and authentic questions. Dukuly and Tanicien break down this nuance: “The best leaders ask questions they genuinely want to know the answers to. To do that, stop and check in with yourself: Why am I asking this question? Do I genuinely want to hear from this person or am I trying to make sure that I don't look bad? Am I checking a box or am I trying to truly engage?”

If you're choosing to reach out to a Black person right now, choose to connect — not do a drive by.

Of course, leaders have a responsibility to check in because demonstrating care and concern is part of the job. “A good rule to follow with all employees is to ‘check in before checking on.’ In other words, make space for feelings and human connection before turning the conversation to work. It’s an opportunity to provide personalized support.”

To navigate these check-in conversations thoughtfully, the LifeLabs team offers the following tips for your 1:1 meetings:

What to say:

How are you, really? Are you sleeping?
What would be the most helpful use of this time? Would you like to talk about what’s going on in the world? We can talk about what you’re experiencing, focus on work, or just take a break.
What’s one thing I can do to make work easier for you right now?
If you need to take time off, what can I do to support you in your absence?

What not to say:

I can’t believe this is happening.
I know exactly what you’re going through.
I feel so guilty.
At least racism isn’t happening at work.
I’m sure it will get better soon.

How to respond:

Acknowledge: I hear you. Thanks for sharing that.
Ask: Do you want to say more about that?

2. Create deliberate space for conversation.

Tania Luna, Co-CEO of LifeLabs Learning

Outside of 1:1 check-ins, company-wide or small group discussions also offer a chance to demonstrate inclusive leadership. “It’s vital to approach the topic of race with respect for the weightiness and nuance of centuries of pain and oppression,” says Luna. “But fears of not knowing how to broach the subject or saying the wrong thing can keep conversations at a surface level — or prevent them from happening altogether.”

Here are the tips to keep in mind as you approach these conversations:

Take an active role: “Silence sends an unintended signal, leaving employees to interpret it in their own way — often seeing no message as a sign of disinterest, fear, or lack of care. To quote my coworker, Ashley Schwedt, inaction is still action,” says Luna. “When having these conversations around bias, microaggressions and exclusion, it’s really important that leaders don’t just hope that everyone figures it out on their own.” Her colleague Dr. Vaneeta Sandhu builds on this point: “Take an active role in those conversations. Invite managers to post articles, blog posts, podcasts, personal stories and discussion prompts. If we want employees to learn more, we have to advertise our own learning,” she says.
Create the space: “Asking employees to be real, present and authentic at work goes hand-in-hand with acknowledging and making space for the very real impact of events outside of work,” says Luna. “The email from Isaac Oates, the CEO of Justworks is a good example. He said: ‘We’re creating space for our own employees to get together, grieve and heal. Space means the venue, time and priority; other things will have to wait.’ The specificity of what holding space means — instead of leaving it as this abstract concept — is so important to spell out.”
Embrace discomfort: “At our LifeLabs internal team meeting, our colleague Robleh Kirce reminded us that we need to choose courage over comfort. Instead of fearing that we’ll say the ‘wrong thing,’ trust that we’ll give each other feedback if we do — that’s the only way we’ll learn to show up for each other,” says Luna.

Expect discomfort, and don’t let it hold you back. Look at it as the price of admission to making progress. Use it as a signal to push you to learn more.

3. Show vulnerability — but set intentions and draw boundaries

Dr. Vaneeta Sandhu, Facilitation Lead at LifeLabs Learning

It’s hypocritical for leaders to ask for authenticity and vulnerability without walking the talk themselves. People need to see this behavior modeled to believe you when you say you really want them to be themselves and say what’s on their mind.

But while the power of vulnerability is increasingly understood, figuring out how that translates to your day-to-day horizon is tricky. One place to start is owning up to mistakes, says Sandhu. “In our research, we noticed that leaders who score high on influence skills share when they made a mistake and what they've learned from it. Mistakes are necessary. When we were kids and we touched the hot burner, we got burned and learned not to do that again. Mistakes are sometimes what it takes for our brains to get the learning encoded,” she says.

We're all going to make mistakes. I've been researching inclusion for 12 years now, and I made at least four mistakes in the last seven days.

Sandhu’s willing to share one of hers: “I was having a conversation with one of my friends who's been impacted by xenophobia and anti-Asian sentiments that have been circling the world since COVID-19 hit. At one point in the conversation, she said, ‘I wonder how much you've been talking versus I've been talking.’ I was focused on myself rather than focusing on another person.”

In these vulnerable discussions with your team, remind yourself you don’t have to have all the answers. “We need to unlearn this idea that we have to have an answer for everything,” says Dukuly. “If a leader can share things like, ‘Here’s how I’ve messed up,’ or, ‘I'm also scared, but here's what I do know and how I'm going to be part of it with you,’ it'll go such a long way.”

We underestimate our teams when we assume that they will demand all the facts or an ironclad plan. People are often just looking for signs of a caring culture — that we’ll be here for them and that, if something’s wrong, we’ll create an avenue for them to share that.

But as a leader, opening up doesn’t mean freely unloading. “There’s an art to being credible and vulnerable or ‘messy’ at the same time. We now have decades of research, beginning with Elliot Aronson’s study on what’s called the pratfall effect, revealing that when people are highly competent, making blunders actually makes them more likable and approachable,” says Luna. “That said, this effect only holds true if you’ve already earned people’s respect by being credible, reliable and competent.”

What’s more is that leaders need to stay mindful of emotional contagion — the tendency for a leader’s mood to be “caught” by others on the team. “As humans, we're biofeedback machines for each other. We feel what others are feeling. Affective labeling research shows that when you put words to what you're feeling — whether it's silently in your own head or out loud — it reduces some of the intensity of that emotion for yourself and others,” says Luna. “Learning how to put our feelings into words is a way for leaders to model and normalize feelings — without hanging those feelings on others and leaving everyone to comfort you. You can say, ‘Hey, just want to flag that I'm feeling really sad today, so I might come across as less engaged, but I’m hanging in there and really want to be here.’”

Tanicien agrees. “I don’t advocate for leaders to be vulnerable without intention. Adding additional context is critical, especially when we're working at a distance in this virtual setting. Otherwise, people might attribute a negative reason for why you choose to do or share something. It’s Hanlon’s razor at work,” she says.

“Give people the reason at the outset by using intention statements. Use phrases like, ‘I'm sharing this because,’ or ‘Here’s why I think you need to know this.’ For example, instead of just saying ‘Sorry I’m a bit distracted today,’ say ‘I’m a bit distracted today, and I'm telling you this because I want to make sure I’m not causing any anxiety by how I might be acting. Or you can just come right out and say, ‘I’m feeling down today, and I’m sharing that so it’s clear that it’s okay for all of us to have our bad days.’”

INCLUSIVE LEADERSHIP HABIT #2: BUILD SELF-AWARENESS AND CURIOSITY:

But it’s not enough to simply make space for conversations around bias, inclusion and anti-racism. Inclusive leaders also put in the work to build their own self-awareness. The simple truth is that while most people want to be more self-aware, many of us aren’t. It’s hard to pragmatically sharpen this key skill. The LifeLabs team breaks down key questions and important reminders as you work to bolster this core behavior.

1. Ask these questions of your past, present and future selves.

“An inclusive leader is aware of their own biases and understands that even if you're a loving, thoughtful, ‘woke’ person, we are all biased. If you have a brain, you’re biased. Sometimes when a bias or an exclusionary habit is flagged, people will get defensive and say things like, ‘I'm trying to be as inclusive as I possibly can.’ Instead, use those moments as an opportunity to get curious. It means there’s more to learn, and that’s exciting,” says Dukuly.

Here are the questions (and the context) the LifeLabs crew recommends leaning on as you look to unearth your own missteps:

Past self: Look back. Starting with your relationships at work, reflect on times when you could have done more to include or advocate for others. Ask: When have I failed to show up for others? Have I witnessed microaggressions and failed to defend a teammate? Is there a time when I actively contributed to making someone feel excluded? What can I learn from these experiences to do better next time?
Present self: Identify and deblur in the moment. “As clinician and author Resmaa Menakem points out, bias manifests in your body. When there's a positive bias, we tend to relax or kind of lean in. When there's a negative bias, we tense up,” says Luna. “Observe your reaction and ask yourself: ‘Why did I just get tense? Would I still feel that way if it were someone else?’ For example, let's say that I have a Black female coworker and my brain is telling me, ‘She's coming across as really aggressive,’ then a good question to ask myself to build awareness might be, ‘Well, would I still feel that way about a white coworker if they were doing the same thing? How about a male coworker? If not, what's causing that reaction in me?’ At LifeLabs, we call these blur word questions. If I'm saying or thinking something ‘blurry’ like, ‘That person's not professional,’ or ‘They don’t seem experienced,’ I stop to ask: What does ____ mean to me? What is the impact I’m actually concerned about?”
Future self: Spot gaps before they form. “Leaders often get hyper-focused on one group within their org. For example, they dive so deep into improving gender parity that they don't look at anything else. Bam, their bias pops up,” says Dukuly. “Do a self-check. Ask: What am I focused on primarily right now and how might other gaps form down the road as a result? For example, when focusing on hiring more women in the workplace, am I forgetting BIPOC, queer, or trans women? You don’t need a firm answer, but the more you can be aware of it, the better chance you’ll have to consider what deliberate steps to take.”

2. Ask these questions of others to consistently practice curiosity.

“Leaders often hear about the importance of demonstrating an open mindset. One way to practice that is by asking questions that are focused on others,” says Sandhu. “This is a simple gateway to growing our self-awareness.”

Great leaders find a way to listen and ask questions more often than they're talking and giving answers.

To consistently practice curiosity as a leader, regularly ask questions like:

What were you hoping I'd speak to in that meeting that I didn't? This question allows you to keep closing gaps between your experience and the experiences of others.
What's important to you about that? If someone's talking to you about something they need or feel passionately about, don’t dive right into how you can help or whether it’s a good idea. That way you can better tailor your support.
What else? “The first response is usually a baseline answer, the ‘I’m fine’ to your ‘How are you?’ To take conversations to the next level, ask questions that require you to go deeper, to fully listen,” says Dukuly. A simple question to keep in your back pocket is “What else is on your mind?” and “Anything else?”

Dr. Vaneeta Sandhu facilitating a LifeLabs training session

3. Direct your own learning — and make sure you’re absorbing it.

But getting curious doesn't always mean having conversations. “I’m a huge advocate of doing tons of self work. There's lots of resources to look at. And yes, the internet is a big swath of information that can feel overwhelming,” says Tanicien. “But push against that by picking one topic and deciding to really tackle it. Make it an active experience by asking yourself along the way: What am I learning? When can I actually apply it? Why is it important to me? Who can I share it with?

People spend a lot of time consuming information, but not actually learning it. Dedicate time to getting curious and educating yourself on new topics — and don’t forget to connect the dots to your daily life.

INCLUSIVE LEADERSHIP HABIT #3: SEEK OUT AND RESPOND WELL TO FEEDBACK:

Receiving feedback is the key that unlocks self-awareness and allows us to provide tailored support, so it’s an important tool in the inclusive leader’s toolkit. But it’s often solicited and received poorly. The LifeLabs team points out common pitfalls and serves up useful tactics for getting better here:

1. Start by focusing on the purpose and intent.

We often hear statements like, ‘Feedback is an important value here.’ But the intention behind that and how people actually perceive feedback is often less clear, ” says Dukuly. “That’s why it’s helpful for leaders to explicitly state things like, ‘When we give and receive feedback here, it’s to enable learning and growth and redefine our preconceived notions.’”

Ambiguous intentions might explain why you’re hearing crickets after asking for feedback from your team. “We’ve all asked, ‘Anyone have any feedback for me?’ and then got, ‘Nope, all good,’ in response, which can be disappointing if you were hoping to get more than that,” says Sandhu.

“Folks might be misinterpreting the intention behind your ask or have anxiety around it, maybe because they've been burned in the past by managers who asked for feedback then responded poorly to it. That’s why it can be really helpful to attach an intention statement. Simple phrases like ‘To help me keep improving...,’ or ‘I’m really trying to communicate more clearly about decision-making. What could I do better?’ can be really helpful.”

2. Ask scaling questions.

“As leaders, we tend to ask very broad feedback questions like ‘How are things?’ You need to get very, very specific. Specificity will allow us to pinpoint exactly where an issue of exclusion might be and understand how we can remedy it,” says Dukuly.

“A tactical practice I love from LifeLabs is what we call the scaling question. A quick example is: ‘On a scale of one to 10, how well do you think I facilitated that meeting? Most of the time, you’ll usually hear seven or eight, because they're uncomfortable saying anything beyond that,” Dukuly says.

“That’s why the second question is magic: What would it take to increase that score by one point? Then maybe I’ll hear something like, ‘You could have called on people more to include other voices.’ This is important for two reasons. One, giving people greater safety to be able to express themselves increases engagement and commitment. Two, it also gives us micro steps we can then act on to build trust and improve inclusion.”

Scaling questions have the power to turn abstract ideas into measurable, actionable feedback. The impact happens through the smallness of the second question.

Here’s another example: If your direct report seems overwhelmed, ask how stressed they are feeling on a scale from one to 10. Say they answer 8. Use these scaling questions to pinpoint how you can help:

What could move you from a 8 to an 7?
How would a 10 look? How about a 1?
What keeps the score from being worse?
When was the last time the score felt good? What was different about that time? How can we apply that today?

When it comes to inclusion, some specific areas to seek feedback around are:

Meeting quality
Opportunities for growth and learning
Opportunities for contribution
Developmental feedback quality
Clarity of performance expectations
Access to information
Feeling that one’s perspectives are heard and valued
Access to social connection and relationship-building

3. Level up how you respond.

But it’s not enough to get better at ferreting out the feedback you need. To up your inclusive leadership game, concentrate on how you can make improvements in responding to feedback you receive.

“We've all been in a position where we've given somebody feedback who said they wanted it, but then you realize they definitely didn't want to hear what you had to say,” says Tanicien.

Luna adds: “As ‘White Fragility’ author Robin DiAngelo points out, white people in particular are usually socialized to avoid direct feedback conversations about racism, so white leaders need to put in extra care to receive the message well and let the feedback sink in.”

For LifeLabs, the key elements of responding well to feedback include being able to:

Say thank you
Ask for examples
Ask about the impact
Come up with an action plan
Hold yourself accountable, whether that’s privately or publicly
Follow up (quickly) to show how you’ve implemented the feedback and ask for more

Here are two more specific tactics to help you put those elements into practice:

Get a high second score.

“Adam Grant popularized this concept of responding to feedback by thinking about the Second Score: When someone’s giving you feedback, they’ve already made a judgement, and it’s out of your control. But you can control how you respond to what they’re telling you — it’s another opportunity to be judged well. Grant frames it in terms of getting an A-plus for how well you take that D-minus,” says Luna.

“This is particularly important when it comes to handling what seem like scary conversations around racism, bias and exclusion. So much of our energy is spent on, ‘Oh my gosh, what did I do?’ or ‘I think I was misunderstood.’ A more powerful mindset is, ‘This is my chance to show this person that I'm going to hear them. I'm going to learn from them. I'm going to give them space to express what they're feeling and needing.’ While you may be panic-thinking, ‘Are they right? What do I do with this?’ instead, ask yourself, ‘How can I reward the fact that they mustered the courage to come talk to me? How can I make sure they feel great about the conversation we just had?’ Your goal should be to leave them feeling encouraged to give you and others feedback in the future.”

Broadcast what you heard.

“Here’s something I’ve picked up from one of the leaders we studied at LifeLabs: Any time she would get critical feedback from someone on her team, she would — with permission — advertise it broadly,” says Luna.

“It can be as simple as passing it along to others in conversations. Saying things like ‘I've gotten feedback that I interrupt people. Would you please keep an eye on that? And if you notice it, please let me know. That's something I'm really eager to be aware of.’ Here’s how I implemented it on my own recently: When a community member gave me feedback, I included it in the postscript of the weekly newsletter that goes out to the LifeLabs community, saying something like, ‘P.S. I recently got this piece of feedback and here’s what I’ve learned from that comment.’ Actions like this help normalize asking for and getting feedback — and encourage others to give you more feedback. It also allows you to share learnings with the group, which can be particularly impactful in times like these when we’re trying to educate ourselves on how to be more inclusive.”

Massella Dukuly facilitating a LifeLabs training session

INCLUSIVE LEADERSHIP HABIT #4: LIFT UP OTHER PERSPECTIVES CONSISTENTLY

The final habit of inclusive leaders is ensuring there’s equal airtime and opportunity. “Inclusive leaders are very deliberate about the equality of their communication. Even when it comes to something like small talk. We tend to do this with the people who we feel most comfortable with, but inclusive leaders go out of their way to check in with those they aren’t already close to,” says Dukuly.

Her LifeLab teammates offer more tips for improving on this critical behavior:

1. Manage the airwaves.

Create spaces in meetings for every person to get airtime to share their ideas, says Sandhu. “Extroverted folks, those who've been on the team the longest, and members of dominant identity groups often get their perspectives heard more than others. Leaders need to pay attention to these dynamics, from how women and people of color are often overlooked, to how folks who are remote, newer to the team, ELL (English Language Learners), or more introverted can find it tough to speak up,” she says.

To get more tactical, Sandhu offers some tools that are helpful here:

One is to create thinking time. “That could be as simple as saying, ‘Before we all answer, let's all jot down our thoughts.’ That's great for people who are operating in their non-native language, for introverts, for those who are neurodivergent and so many other groups.”
“Another effective tool is a forced turn-taking mechanism like a timed round-robin, where you say, ‘We're all going to go around and share a question or an answer for two minutes each. Feel free to say pass.’ There's a lot of research, for example, in the surgical world — popularized by Atul Gawande — that shows if surgical teams start surgery with a round-robin, nurses are much more likely to speak up in the midst of surgery and potentially give lifesaving, critical feedback.”
Ritual questions are also impactful. Make a habit of ending key points in a meeting with questions such as, “Who haven’t we heard from yet?” and “What are two additional perspectives we haven’t considered?”
While preventing interruptions in the midst of an engaged conversation — especially a virtual one — can be counterproductive, one thing leaders can do is track completion. “If someone is talked over, go back to them and say, ‘Hey, did you want to finish your thought?’ or ‘I’d love to hear the rest of their point before we move on.’”

It’s not enough to make sure everyone has a seat at the table — inclusive leaders make sure everyone gets airtime, too.

2. Tackle microaggressions, head on.

“This is something that is particularly challenging right now. There's a growing understanding of the weight and pain of what are often called microaggressions in social psychology — a term first coined by Chester Pierce. These are seemingly small comments or actions like, ‘Where are you really from?’ (said to a non-white coworker) ‘You look like a real woman!’ (said to a transgender coworker) or ‘You’re so articulate,’ (said to a Black coworker). These are often unconscious signals we send to people that they don’t belong or that we hold low expectations for them. Author Ibram X. Kendi goes so far as to call them ‘racial abuse,’” says Luna.

“Leaders bear a huge responsibility here. If you’re serious about being more inclusive, you can’t sweep comments like that under the rug. When you encounter microaggressions, you need to meet them with micro-interventions,” she says. “There is so much talk of being anti-racist right now. It’s concrete actions like these that actually challenge the normalcy and invisibility of daily racism.”

Start by preparing before it happens by thinking about how you’ll respond. “What will you say out loud? In what instances will you jump in and say something in public and in what instances will you give feedback in private?” says Luna.

When microaggressions do take place (and they will), consider your options. “You could talk to the person who might have been impacted and say, 'Hey, would you like me to say something? How did that feel for you? What might you want me to do next time?’” says Luna. “You could also pull aside the individual who made the microaggression. At LifeLabs, we use this short video in our Behaviors of Inclusion training to demonstrate how it might look, but essentially you can say, ‘Can we talk about that comment you made? I noticed that when you said XYZ, the other person didn't engage as much afterwards. I've been there and I've said stuff before that didn’t land like I intended. Would you be up for talking about it?’” says Luna.

“The bottom line is that you need to make a plan for how you’re going to show up as a more inclusive leader — otherwise you very likely won’t. As is often said in the world of DEI, if we don’t intentionally include, we will unintentionally exclude. And we simply cannot afford to keep doing that.”

Photos courtesy of LifeLabs Learning. Cover image Klaus Vedfelt / Stone / Getty Images Plus.

Jun 18

Hire a CMO

Jun 18

Taking Care of Your Health While Running A Startup

Jun 18

Preparing to Fire an Executive

Jun 18

Standard Financial Model

Jun 18

What Your Next Head of Product Looks Like

Jun 18

Make Operations Your Secret Weapon - Here’s How

At Etsy, COO Linda Kozlowski spearheaded international expansion, unified and started growing its marketing plans, began redefining the company’s brand, launched a new communications strategy, and kicked off the integration of user feedback into product development — all in about six months. While others might just credit her capabilities, she’s quick to cite the plan that CEO Chad Dickerson laid out. He outlined not only how her specific acts would make a difference for Etsy’s customers, but also how her role would link to the rest of the leadership team — especially Dickerson. That exactitude bred effectiveness.

Kozlowski is part of a new crop of COOs who are harnessing know-how from a range of roles to create systems that elevate the entire company. At places like Evernote and Alibaba, she’s held leadership roles in global expansion, marketing, public relations, customer experience and business development. Decades of broad exposure has not only shown her which levers make each functional area work, but also how they can be coordinated for a startup to succeed.

At First Round’s CEO Summit, Kozlowski puts a spotlight on the most mysterious role in the C-suite. She outlines why and how companies should make operations their core and how to determine the COO that’s right for you. Kozlowski shares what an operations leader is — and is not — in order to set the position up for success at any startup.

What is a COO and why do you need one?

It’s common for startups to wait too long before bringing on an operational leader due to the lack of clarity around the role. It’s more intuitive what other C-suite roles do: a CMO leads marketing and a CTO oversees engineering. But it’s less apparent with a COO. Even a quick Google search for definitions leaves much to be desired: “a senior executive responsible for managing the day-to-day operations of a company.” But don’t functions have their own ops team, such as sales and sales ops?

“We’re all familiar with tech operations, but what COO really means, is business operations: how you operate your business, think about strategy, and move the business forward in growth,” Kozlowski says. “The COO role is custom to every company and requires deep self-awareness from the CEO and founder to outline the specific skills and qualities they need in a partner.”

The COO role is entirely defined by its relationship to the CEO.

Self-assess to find your counterpart. If your executive team was a film crew, your CEO and COO would be the director and producer. “Your COO must be a complement to the CEO and the rest of the executive team if you have a shot at radically transforming your organization,” Kozlowski says. “The required skills will be different for every company, leadership team, and stage of business. My areas of strength are around scaling companies with significant global presence through strategy, marketing, and a consistent customer experience. I work best with a CEO with a technical background whose strategies I can help make work at scale as we go to market. But it will be different for each company based on stage and the composition of the executive team, and it will evolve as you grow. Be prepared to accept and adapt to your needs.”

Determining the right candidate requires deep introspection and what Kozlowski calls Self-Awareness 301: an advanced course in pinpointing your strengths and weaknesses and thinking very seriously about how those attributes influence the way you manage your business. Ask yourself these questions to unveil the traits you need in a COO.

What am I drawn to? You enjoy, default, and excel at these tasks. Write them down. Seriously. Return to them and note how they structure your day and management style.
What do I procrastinate on? We all have those lingering items in our inbox or to-do list that we push off or tell ourselves ‘I’ll do that tomorrow’ but never do. It may be you don’t have enough time, but there’s likely a skills gap you need to admit. Create a list when they occur to you and make sure they are traits and abilities in your COO.
What do I wish I knew and liked? Of the things you delay or just skim the surface on, what do you wish you had a better command of or affinity for? You’ll eventually be adept at and attracted to these areas, but in the short term, you need to find ways to develop them. Your COO should act as an instructor to guide you.

Answer these aforementioned three questions on your own first. It’s unlikely that there’s another co-founder or colleague has been working with you every step of the way throughout your career. So you’re the best judge of what you love to do and where you need to improve. Once you have answers to these questions, Kozlowski recommends enlisting others as a sounding board. These might include your executive team, board and investors, mentors, partner or executive coach. “Don’t guide their thinking or come with too many prefaces. Whether expressed verbally or in writing, encourage them to weigh-in on who you are, the roles you excel in and the areas where you need to grow,” says Kozlowski.

“There is a caveat when you’re asking your executive team, board, and investors for critical feedback about where you need to improve. As CEO, especially of a young company, you’ve likely been working tirelessly to promote yourself and prove your leadership so people will commit to and invest in you,” says Kozlowski. “This is not the time to reassure them that you know how to do everything. You’re looking for candor, not an echo. Ask for feedback and be silent. Thank them for whatever they play back to you.”

Customize and choose your counterbalance. Now that you know what you need, you can start to seek the COO who is most capable in helping you scale your company. According to a Harvard Business Review article, there are seven types of operational leaders. Given that the COO must be a complement to the CEO and founder, you’ll likely need a combination of the roles to distinguish the right partner for you.

“I’m The Other Half and an Executor, which are a pretty common types. The CEOs I have worked with tend to have complementary skills to mine. In tandem, our abilities are better than on their own,” Kozlowski says. “For example, with a CEO who brings a grand vision to a company, I can bring a scalable execution of that plan. For another CEO who has mostly done business in the US, I bring significant experience scaling globally.”

Of course, there are different CEO-COO pairings. “You may be seeking the Heir-apparent, someone you’re training to be the next CEO. Or if you’re a younger founder, perhaps the best choice is an experienced mentor who can impart wisdom and help shepherd the business,” says Kozlowski. “There’s no perfect formula, and many COOs are a combination of two or three types. The COO who’s right for your company depends on the skills the CEO is lacking and need to develop — that’s especially true for younger CEOs.”

Search for candidates in unexpected places. Don’t just put feelers out for MBAs or veterans of finance. Kozlowski spent nearly two decades in PR and Communications before she moved into marketing and operations at Alibaba. “It was a great fit because the skills I cultivated previously were right for the role: anticipating problems, communicating a clear vision, understanding what’s going to be asked next and how to get out of trouble when things go wrong,” she says. “I rely on these skills every day as COO. Don’t limit your search parameters at the onset.”

The right COO is not about pedigree but precise fit.

The Five Traits of an Operations Champion

Regardless of the type of COO you need, there are certain characteristics that non-negotiables for an operations leader. Here are five to hone in on when you’re vetting candidates for the role:

Trust. There’s a reason why this word is referenced a lot in business — but it’s especially critical between the CEO and COO, given how synchronized they must be while making decisions on the fly. “You can’t run a business with someone who is supposed to be your other half if you don’t have an honest relationship with them. Period. It’s not only about trusting their instincts and capabilities, but also about knowing viscerally that they’ll step into the chaos with you, tackle their share and watch your back at the same time,” says Kozlowski. “It’s a challenge to see if there’s that potential for trust at the onset. A new COO — as with any new employee — will want to show how she’s commanding each part of her new job. But don’t forget to use the CEO as a sounding board for a particularly challenging choice early on. Come with options, intelligence and an opinion, but also a vulnerability and genuine ask for input. It’s not only a chance to come together during a difficult decision, but shows that you trust two heads will be better than one early in the relationship.”

Proven Execution. The best operators are relentless doers. “Ask candidates to provide specific examples that demonstrate an ability to move projects forward. Pay attention to how many instances they cite, how far back they go and at what cadence or interval,” says Kozlowski. “You’re not looking for one-hit wonders, but those who reset to jump hurdle after hurdle. Consider asking them what and how they’d contribute first at your company. Look for clear answers rooted in proven strategies and tactics.”

With a COO, you want a person who is poised to lead her position, not leap in position.

Ego checked. According to Kozlowski, the best operations leaders are humble, hungry and ready to work. “COOs are often thought of as the heir to the CEO, but aren’t there yet. It’s vital that your candidate has their ego in check and clearly understands their responsibilities supporting the business,” says Kozlowski. “Ask them about their advancement in past roles and what motivates their growth? It’ll help you get an understanding of their career goals and incentives. Ask references for detailed stories about how candidates have handled instances in which they were wrong.”

Chemistry with the CEO. COOs are true partners, not colleagues. The adage ‘don’t hire who you like, hire the person who can do the job’ doesn’t entirely apply to the COO role. Kozlowski advises founders and CEOs to be forthcoming about the relationship they envision having with their COO. “You’re going to be spending a majority of your time together. You need to have a personal connection where you actually enjoy being with them, listening and talking to each other, and working together,” she says. “Go above and beyond thinking about how you’re going to test for personal fit during the interview process. Rather than failures, I like to ask about a time they were embarrassed or uncertain about something, and how they navigated it. That gets to both problem-solving and the human side. I also like to touch on other working relationships that were very successful as that really helps cut through small talk and helps better assess if there might be chemistry. What you’re seeking is a foundation to build a real relationship.”

Versatility. Adaptability must be their default mindset. “Your COO is second in command and will be your team’s go-to when you’re not in the office. They should exude similar leadership traits to the ones you possess so your team feels confident relying on them — and the business doesn’t skip a beat,” says Kozlowski. “The most successful COOs are jacks- or jills-of-all-trades. One way to identify this trait in the interview process is to press on a wide range of growth challenges — from hiring an executive team to fundraising — to see how candidates shifted their focus during inflection points in a company’s development.”

As you identify these key qualities, also be aware of the following red flags. According to Kozlowski, your operations leader is not:

The CEO. This goes back to the ego check. Your COO must accept and internalize that their job is to run the plays, not call them.
A babysitter. A COO is not a nanny or handler for a CEO. Sadly, this is a disturbing trend and one that is destined to fail the duo — and the company. Do not hire a babysitter.
Someone who needs a ‘C-title’ to join. If you need to add Chief to a candidate’s title to persuade them to join, don’t add them at all.

Linda Kozlowski at the First Round CEO Summit

The Right Time to Hire a COO

Given how ambiguous a COO job description is to many startup founders, the timeline can even be more of a mystery to crack. And yet every company needs someone to lead operations. The key is to start thinking about it and preparing before you are ready. To figure out timing, Kozlowski isolates some key variables, such as if you’re creating a physical or digital product or how you assess your own personal leadership style. Here are her tips:

Hire immediately if you produce a physical product. COOs are the backbone of companies that produce tangible goods. “Logistics and operations make or break starting and scaling a CPG or hardware company. You need someone with past experience making a physical product who can contribute to, structure, and oversee the development, manufacturing and shipping from end-to-end. Enlisting someone in this role from day one is the difference between shipping your product on time and missing your launch.”
Hire when you hit product/market fit if you build digital products. COOs take digital products to the next level. “If you’re building a digital product, it’s time to hire an operations manager when you’ve reached product market fit and are ready to scale. COOs are accustomed to building and managing fast-scaling operations,” says Kozlowski. “Hiring someone before you’re ready to grow — such as if you’re still in beta — will leave the candidate and you frustrated at lack of measurable change and progress. It doesn’t mean you can’t start your search early; just don’t do it until you have engaged, delighted users.”
Hire immediately if you, founder or CEO, are fully immersed in building the technology. According to Kozlowski, this rule trumps the other two. “If you are 100% immersed in building your technology and don’t want to run the day-to-day, don’t try to go without a COO. Hire an operations leader who can run the logistics side of the business so you can focus on developing the product,” says Kozlowski. “I see this a lot at early-stage companies. It doesn’t mean their CEOs or founders can’t or won’t develop these operational or management skills. But they simply need someone who thrives on establishing and scaling processes to guide and grow their companies.”

On Onboarding an Operations Leader Well

If you’ve found, attracted and hired a COO, the last critical step is to integrate them. Again, because the COO is so frequently a misunderstood role, it's often one of the fastest to fail. CEOs and founders, be hyper-vigilant with how you introduce your COO to the team. Here’s how:

Be specific with the company on why now. The biggest mistake Kozlowski sees CEOs and founders make is saying: “I’m hiring a COO because I need help.” Instead, ask yourself the following questions to help you prepare and craft a strong narrative to share with your team:

What kind of help do I need? Why do I need it? How will it address an obstacle?
How strongly is this obstacle influencing the company?
What exactly will this person do to alleviate the impact from this obstacle? How will that change over the next quarter and year?

“We’ve been able to implement and scale operational changes at Etsy because Chad made the growth opportunities incredibly clear to me and the rest of the team. We collectively agreed on our goals from the start,” Kozlowski says. “For example, one opportunity facing Etsy is how to grow and scale marketing both in the US as well as abroad to support buyers and sellers overseas. Given my international scope of my work at Evernote and Alibaba, I joined to complement the existing strengths of the executive team in how we could each leverage areas for growth. Chad defining these roles and giving true autonomy to each role was key to a fast integration and a strong team.”

A COO helps you cover double the ground, as well as double-down. She should be seen as a multiplier.

Pass the baton with an Olympian's precision. As CEO and founder, you’ve likely built deep relationships with your direct reports. Explaining that they will report to a new executive is among the trickiest — and most telling —parts of the integration of a COO.

“Team members will want to keep reporting to you as the CEO, despite the updated org chart. The way a CEO handles this transition can either underline or undermine the importance of a COO,” says Kozlowski. “Most founders keep coaching and doing 1:1 meetings with their people — after all, they were there from the start. But this is one of the most dangerous traps. Instead, have the COO join you and slowly start leading meetings. Help the COO build relationships with the team and make it clear what the new structure looks like. It’s takes vigilance as much as time, but it’s a critical step.”

The transition won’t happen overnight and team members will still come to you if and when they don’t get their way. CEOs must explain why an operations focus is necessary for the company and direct them to the COO. This was especially important during Kozlowski’s integration into Etsy. Chad introduced Kozlowski to the company via the all hands meeting before she even started, getting everyone excited about the additive skillset to the leadership team. He was clear about her areas of responsibility right from the start, which meant that her first day, everyone was prepared to jump in and work with her. Ultimately, all of the effort you placed into sourcing and closing the right partner can be lost at this point. Actively manage the process with empathy and resist the urge to micromanage.

Tying It All Together

Before a COO can be a possibility for a CEO and startup, it must first be on the radar. Start with a short self-assessment of your strengths and weaknesses as a CEO or founder. Complement that with perspectives from your existing executive team and advisors. Define your counterbalance and use the seven types of COOs as a tool. When interviewing look for the five traits needed for any type of COO and beware the three most common red flags. Hire a COO immediately if you are building a physical product, and after product/market fit, if you are working with a digital offering. Be as conscientious in integrating the COO as you were in hiring her. Your approach will either propel or dispel her reason for being there.

“Finally, don’t forget to let it go. As a founder and CEO, your company is your baby and you’re probably holding on bit too tight. Yes, you should always have a pulse of what’s going on, but until you actually hand over the reins, your COO won’t have an opportunity to make any real changes,” says Kozlowski. “Focus on what you need to do. Don’t micromanage her. The sooner you give away those responsibilities, the faster she can execute in her role. When you set your COO up for success you don’t lose control, but actually have more command over your company’s future.”

First Round Capital

Jun 18

All Hands: Take Questions in Advance

Jun 18

An Entrepreneur’s Guide to Finding a Coach

Photo: Matt LaVasseur via Unsplash

I’m frequently asked by entrepreneurs, investors and friends how to find and select a coach. It turns out there aren’t a ton of useful resources out there. I figured this was a timely opportunity to create and publish a comprehensive guide to help those leaders committed to professional and personal development.

I’m clearly biased but I believe that every leader (and person for that matter) can benefit from working with a coach, especially in times of crisis. I’ve seen first hand the impact that coaches and mentors have had on my own transformation. I’ve also witnessed the growth that other leaders have experienced. This includes countless founders I’ve partnered with, close friends and even my wife.

That’s why I designed a guide to help you navigate the opaque world of coaching. I also created this guide to help you assess and find an amazing coach who is a strong match. Fit is incredibly critical because it has a direct impact on the strength of the alliance and quality of outcomes.

This guide is broken up into a number of sections. First, I provide an overview on what coaching actually is. I then share insights into the coaches toolbox. Said another way, the experiences, skills and certifications that a coach may have. From there, we’ll dive into how you can run a process and determine fit. I then highlight coaches and organizations that have been recommended by your peers. On our way to wrapping up, I share how you can think about pricing and ROI. Finally, I leave you with some resources if you want to go deeper into coaching.

With all of that out of the way, I’m thrilled to present to you ‘An Entrepreneur’s Guide to Finding a Coach.’

Working with a coach is a big investment in time, money and energy. Both sides should feel charged to co-create a partnership, embark on a life-changing journey and grow together over time. That’s why going into the process armed with guidance and information is so critical.

There are also some excellent blog posts on the topic if you would like to go deeper. There’s no way I would have been able to create this guide without the help and influence of others. Here are some of my favorites from Ed Batista of Stanford, Beth Scheer of Homebrew and Richard Hughes Jones, a wonderful coach out of the UK.

Remember, there are thousands of amazing coaches out there with different life experiences, philosophies and approaches. The right one is out there waiting for you to connect with them. I sincerely hope you find and partner with a coach that helps you fulfill your full potential and bring your wildest visions to life.

Finally, I view this guide as a work-in-progress. Your feedback, questions and comments are welcome, encouraged and appreciated. Don’t hesitate to reach out. I’d love to hear from you.

Now go make it happen. Godspeed!

Steve Schlafman

Jun 18

Why do new leaders need a therapist?

Jun 18

Square's Onboarding Checklist- First 90 days

3 Ways to Run a Productive Retrospective

Article

Jun 18

3 Ways to Run a Productive Retrospective

Jun 18

Inclusive Leadership - Practical ways to foster an inclusive environment

https://mcleanonline.medium.com/inclusive-leadership-efbc6c46aac2

At Elsevier, we place strategic importance on having inclusive, engaged and agile teams. Therefore we value having an inclusive environment for our teams to operate in where everyone is treated fairly and respectfully, has equal access to opportunities and resources, and can contribute fully to the organization’s success.

An inclusive culture enables a high-performing and engaged set of employees, where people feel valued and can bring their whole selves to work. A culture of inclusion increases diversity while also improving innovation and team / business performance.

Leaders have akey role to play in fostering an inclusive environment. Whether we are senior executives or managers, leaders’ behaviours can drive up to 70 percentage points difference between the proportion of employees who feel highly included and the proportion of those who do not —a phenomenal difference.*

All of our product leadership team recently completed a training course with the NeuroLeadership Institute on inclusive leadership, in order to help us embed habits and behaviors that will help to shape such an environment. Following the training, I read Anna Shipman’s post on an inclusive leadership course that she had attended, and that sparked me to do something similar, in order to help me to distil, remember and embed what I learnt.

(Of course, what I’ve written here represents only a fraction of what we covered in the training course — three 90-minute workshops and assignments in between — and I’ve included bits I’ve picked up from other reading I’ve done recently on the subject — which I’ll publish as a separate reading list.)

The SCARF model (R)

The course introduced me to the SCARF Model (a registered trademark of the NeuroLeadership Institute), which is a way of describing and understanding social threats and rewards and how our brains respond to other people’s actions:

For an overview on The SCARF Model (R) and the effectiveness it has in the workplace, you can read this blogpost or this one or this one by Itamar Goldminz, or watch this video:

The theory is that what motivates us socially is different for each of us. That is, we are all sensitive to these five domains — but to different degrees. For example, some people may particularly value ‘status’ (eg getting credit for a job well done), while other people crave ‘autonomy’ (a sense of control over the work we do, and not being micromanaged). Some people are more sensitive to threats relating to ‘fairness’ (eg a lack of equity/equality in social interactions), other people are more sensitive to threats relating to ‘certainty’ (eg when roles or responsibilities aren’t clear) or ‘relatedness’ (eg feeling different from others or excluded).

As an aside: if you want to understand which domains of social threat and reward matter most to you, you can take an assessment at the Neuroleadership institute’s website. Note this assessment is for individual use. If you wish to use the assessment with your team or organization, contact the institute.

By being sensitive to these five domains, leaders can help meet the needs of the people on their teams. How we act and behave can impact each domain and thereby lead people to feel more or less included and valued.

Finding Common ground

‘Relatedness’ is the sense that we belong. Leaders can do many things to foster strong relationships and to help create a feeling of common ground among colleagues. For example:

Leaders can use language such as “we” and “us” to promote that feeling, instead of language like “you,” “me,” and “they,” which signals a clear boundary between groups. [1]

Leaders can also:

hold regular 1:1s
check in regularly with team members, particularly remote workers
encourage time at the start of meetings for non-work conversations
look at the person speaking in a meeting, nod, and smile
offer words of empathy and concern to colleagues
look for shared experiences and similarities
ask for help
introduce buddy systems or mentoring arrangements

We are likely to work against people’s feeling of common ground and an inclusive environment:

if we are distracted when others speak
if we focus completely on business
if we focus on differences
if we talk about “resources”, when we mean people [source]

Original tweet: https://twitter.com/ewebber/status/979374038144421894

Actions to create an inclusive workplace (from Catalyst): https://www.catalyst.org/research/be-inclusive-every-day/

Lift people up

Leaders have a particular role to play in maintaining fairness and have a disproportionate impact in building other people’s sense of status at work (eg through recognition and reward).

Leaders can go a long way in promoting fairness through acts of transparency. For example, when making decisions, leaders can communicate their thought process behind making one choice over another. When employees don’t get the full picture, and start to invent alternate stories, it may increase the chance people feel slighted. [1]

Positive behaviours leaders can adopt to foster an inclusive environment include:

Seeing mistakes as a necessary part of growth
Admitting mistakes and apologizing
Seeking feedback, especially from more junior colleagues
Rewarding fresh thinking and taking risks
Inviting people to express concerns
Giving everyone an opportunity to contribute and actively encouraging more junior people to speak up
Being curious: listening without judgment, and seeking to understand
Regular giving positive feedback and showing appreciation
Sharing employees’ accomplishments to the wider team — or giving them the floor to do so themselves
Introducing a regular mechanism for everyone to share what they are working on and their achievements

On the other hand, leaders may erode employees’ sense of status:

if they squander new ideas or take credit for others’ work [1]

if they are tough on mistakes
if they stick with the status quo
if they give only corrective feedback

10 actions men can take to create an inclusive workplace (from Catalyst): https://www.catalyst.org/wp-content/uploads/2019/01/actions_men_can_take_2018.pdf

Create autonomy and clarity

People generally like to know what’s going on and to feel a sense of control over the work we do (‘autonomy’ is one of the three key elements in Dan Pink’s framework for workplace motivation):

When leaders involve themselves with every little detail of their team members’ work, they risk creating threats to those people’s autonomy. (This is why micro-managing feels so offensive.) However, when leaders give employees the time and space to do their work, unfettered by interruptions, they send a much more rewarding signal that they trust and value the person’s ability to get things done.[1]

As leaders we can help provide autonomy and clarity by:

being clear on what we expect from others
helping people to break down complex work into smaller, more understandable chunks
including others in decision-making
clarifying roles and responsibilities
clarifying objectives
allowing people to take on more responsibility, and to use their initiative
giving people the freedom to try out new ideas
ensuring that everyone who needs to know does know
sharing your thinking
having other people share their goals to ensure alignment

Conversely, we threaten people’s autonomy and sense of clarity by:

leaving people out of the loop
assuming everyone shares the same goals
keeping our thoughts to ourselves
allowing meetings to go on too long, without any clear end in sight

Other practical tools:

Take the quiz: Are you an inclusive leader? from Catalyst
How inclusive are you? — diagnostic quiz from Kornferry
How to run inclusive meetings— Catalyst
Core Needs: BICEPS —this is another model for thinking about what people need, from Paloma Medina (The BICEPS acronym stands for: Belonging, Improvement, Choice, Equality, Predictability, Significance. There are many parallels with the SCARF MODEL: ‘Belonging’ is similar to ‘Relatedness’ in the SCARF model, whilst ‘Choice’ relates to ‘Autonomy’, ‘Equality’ to ‘Fairness’, and ‘Significance’ to ‘status’.)

Richard McLean

Jun 18

Managing Unconscious Bias

Jun 18

Black History Month - February 2021 Calendar

Jun 18

Resources for Recruiting & Retaining a Diverse Team (with a focus on Women in Tech) | by Chaya Cooper | Chaya Cooper | Medium

https://medium.com/chaya-cooper/resources-for-recruiting-retaining-women-in-tech-d845495b87f9#.rmn7rk8j7

You’ve decided to hire more Women in Tech… Now what? I’ve rounded up my favorite tools and resources for recruiting and retaining diverse candidates.

Tools for Diversity Sourcing & Removing Unconscious Bias:

Diversity Sourcing: Boolean Search Strings for LinkedIn — Some “starter” queries for Boolean search strings for diversity sourcing on LinkedIn
Managing Bias — A suite of videos and resources released by Facebook around unconscious bias, addressing job postings and interviews, as well as on-the-job interactions.
NPM’s Guidelines for writing job posts for diversity — Short and sweet job description guideline, with link to an open source repo of former job descriptions.
Textio — Easy-to-use platform for optimizing job descriptions by uncovering key phrases and unconscious gender bias.

Specialized Recruitment & Consulting Firms:

Awesome Co - Surfaces diverse talent for tech companies. [New York City]
Blendoor - Mobile job matching app that hides candidate name and photo to circumvent unconscious bias and facilitate diversity recruiting in tech companies.
ChickTech Jobs - Job board that helps companies find qualified female applicants to build diverse technical teams.
Paradigm - Has helped companies like Slack and Airbnb identify strategies to more effectively attract, hire, develop, and retain a diverse workforce.
Power To Fly - Recruitment firm specializing in remote jobs for women in tech. [Global]
Savvy - Recruitment service for motivated women (apx. 40% currently in STEM). Only works with companies focused on equal hiring, promotion and pay initiatives.
Tech Ladies — Connecting its community of 20,000+ women in tech with the best jobs and opportunities in tech. [Global]

Women’s Tech Communities:

Chicago Women Developers - Community of women who love to code or want to learn [Chicago]
Ladies Who Code - Brings the brightest female minds together to code, talk tech, share ideas and innovate via global meetups & conferences [Global]
Latinas in Computing - Community created by and for the Latinas in computing
Lesbians Who Tech - Community of queer women in & around tech (and the people who love them)
Linuxchix - Network of women working in Linux around the world. Includes Chicas Linux, a chapter devoted to supporting Spanish-speaking women in Linux. [Global]
NY Tech Women - Organizes educational and social events for 500+ female technologists [New York City]
NY Women In Tech - Organizes networking and social events for women in tech [New York City]
NYC Tech Ladies - Organizes monthly meetups and an active online community of 1000 women in tech [New York City]
Systers - One of the world’s largest email communities of technical women in computing [Global]
Women’s Coding Collective - Community of women who create for the web [Boston, Global]
Women in Machine LearningNetwork of female computer scientists in machine learning [Global]
Women in Tech - Membership organization for women in tech [Global]
Women Who Tech - Brings together 2800+ talented and renowned women breaking new ground in technology who use their tech savvy skills to transform the world and inspire change [Global]

Lists of Top Women in Tech:

Tactics for Recruiting & Retaining Diverse Candidates:

The CEO’s Guide To Building Diverse Teams (And Keeping Them That Way), Amy Sample Ward, FastCompany — How to take advantage of the diverse staff you’ve hired with every project

Additional Resources:

Thank you to Allyson Kapin and the wonderful community of Women Who Tech for introducing me to several of these resources.

Jun 18

How to Get Funding For Your Startup That’s *Not* Venture Capital

Jun 18

Here’s How to Wield Empathy and Data to Build an Inclusive Team | First Round Review

When Ciara Trinidad left her post as Lever’s Head of Diversity and Inclusion, the numbers made her understandably proud: The startup’s team of 125 people was 59% women, 39% men, and 2% gender nonconforming. Even the sales team — historically a male-dominated group — had a 50/50 gender split. “The product team was at about 40% white; the majority was a mix of every other government-issued race or ethnicity,” she says.

At a time when tech knows diversity and inclusion is crucial, but can’t seem to get there, it’s a remarkable achievement for the company’s first D&I leader. So can she pin that success to her advanced degree in human resources management? A long resume of previous positions in this field? Nope, that D&I leadership role was her first. In fact, when she began at Lever as employee #12, she was a Customer Success Manager. Before that, she held a variety of roles at Apple — from Specialist to In-Store Trainer to Lead Genius. Today, she’s not only Head of Diversity, Inclusion and Belonging at Blend, but has advised companies like HotelTonight and Lob.com on their D&I strategies.

In this exclusive interview, Trinidad shares how she got the job done with two secret weapons: empathy and data. She explains how to build a dashboard to surface your hiring numbers, and why a culture of data underpins a culture of inclusion. And she notes that, when it comes to building your D&I team, project-management chops and a passion for doing the work are the only bona fides you really need.

WHY DIVERSITY AND INCLUSION FOR YOU?

To really be successful in building your strongest, most diverse team, you first need to believe in why you’re doing it. And Trinidad knows firsthand that the benefits are numerous.

“One thing that's really interesting about helping to build a company that is so diverse — and so visibly diverse — is this idea that you create a really safe environment right off the bat,” she says. “I’m multiracial. I’m also queer. And I’m also a woman. I tend to be an outlier in most environments. So I know that when you’re part of a team with such an even spread as far as diversity, you find yourself more comfortable expressing things you might not express otherwise.”

Leaders are increasingly savvy to the fact that a diverse workforce also boosts the bottom line. The reasons why touch every aspect of your business. “When you build a culture where people can be their authentic selves, they're going to bring their best work, their best ideas and their best people to your company,” says Trinidad. “That comfort turns into action — and becomes a competitive advantage. People see that they don’t have to look outside of your organization to tap into their full potential.”

That’s particularly valuable when it comes to retaining a millennial workforce. “Statistics show that the average millennial switches jobs every 18 months,” says Trinidad. “My god, a number of us were in college for four years. We're talking about less time than it takes to get an associate’s degree. And people are getting up and leaving. The real reason behind that is typically that they don’t have a sense of belonging, and they're not satisfied with their growth path.”

Building an inclusive culture takes research, thought, and even a willingness to be uncomfortable. Too often, though, companies settle for lip service, stating goals first and asking questions later — or not at all. “People will say, ‘We really want to increase our number of women.’ And my question to them is always ‘Great, why? Why is that so important to you? What do you believe that women are going to bring to your organization that you don't already have?’ And they have no idea,” says Trinidad. “Or worse, they just latch on to lingo, like ‘diverse candidates.’ But if they stopped to think about it, they’d stop saying it. Because they’d realize that 'diverse candidates' is not a thing. There's no such thing as a ''diverse candidate,' because that's assuming that any two people are the same people.”

If you’re simply saying what you think you should with D&I, your initiatives are set up to fail.

Without that intentional inquiry upfront, here’s what happens: companies proudly announce that diversity is their top priority. When pressed for the details of their family leave policy or research on their employee’s top concerns, though, they come up empty. “I’ve seen it time and time again,” says Trinidad. “To me, the biggest mistake you can make is starting to talk at events and write blogs about these things before you’ve actually done anything.”

Not only is that antithetical to real cultural progress, it’s a big liability when it comes to hiring the very candidates you’re ostensibly looking for. “That’s a red flag to people like me. If you start by saying, ‘Diversity and inclusion is really important, but there aren't a lot of resources within our organization,’ I'm immediately going to question your integrity and why you’re telling me about D&I at all,” says Trinidad. “It doesn't matter how sexy of a brand you have or your latest valuation. If you tell me that you're something you're not, I'm not going to stick around.”

A culture of inclusivity is all about authenticity, so start with how you approach this vital topic. Settle in, shed your assumptions, and determine where you can effect real change. The first step? Become an avid consumer of your organization’s hiring data.

“I rely really heavily on data,” says Trinidad. “Diversity professionals might read that and roll their eyes, because we’ve all been working on data. But it's more than just using the data behind the scenes. It’s about presenting the data to every party that has a stake in the game.” To that end, she starts by creating a dashboard that consolidates the data in the clearest, most digestible way, then she gets that information in front of the stakeholders who need to see it.

At Lever, Trinidad started with the sales org, which, when she started in her D&I role, was 80% white. “Let’s be candid: Tech sales being white is an age-old issue. It's a problem that most organizations share, and that's just how it's been for a very long time,” she says. “A lot of people are looking to figure out how exactly to fix it. Well, step one is understanding that your biases exist.”

Fixing this problem wasn’t a matter of telling recruiters what they were doing wrong. It meant looping them into the conversation, combining their expertise with the story bubbling up in the data. Together, Trinidad and the recruiters began building the narrative of why the numbers looked the way they did.

“We sat down together and looked at each department within the sales organization. We also talked about how those hires looked over time. I showed them the dashboard that said, ‘In Q3, these are the numbers. We made this many hires. Of those hires, this is how many were white. Let’s talk about why.’ By showing people managers their diversity dashboards, they feel like they are a part of something. And then they’re able to ask really specific questions to start solving problems.”

Discussion gives muscles to data — especially around D&I. Without it, a dashboard is a depository. A dialogue becomes a monologue, which eventually becomes silence.

Develop Your Dashboard

Your diversity dashboard is a product, so build it like a program manager. First, ask yourself: what is the problem this tool needs to solve? “Great Diversity and Inclusion leaders are actually really strong program managers and listeners,” says Trinidad. “These are people who get to the core of a challenge. My problem was that I could see and feel what we needed to focus on. But I didn't have a concrete story to tell that explained why. So for me, building a dashboard was all about understanding how Lever grew and the patterns and trends that we saw in our growth over time.”

Next, educate yourself on where your organization’s data is stored. “Data sources are important. Number one is your HRIS [Human Resources Information System]. It's literally your mother lode. If you don't have an HRIS right now, that's fine. If that’s the case, chances are you keep employee information in a spreadsheet,” says Trinidad. “But know where it is. Does all the data live in my HRIS systems? Does it live in my applicant tracking system? Is there a lot quantitative data sitting in the software that I use for performance reviews?” To answer these questions and get to the bottom of it, Trinidad partnered with Lever’s HR Operations Specialist, who walked her through how and where Lever’s data was collected.

From there, you’ll need to determine which data points are relevant to the questions you’re investigating. “On my first attempt, I had all the data from our HRIS exported, which — spoiler alert — is a really big mistake. There's so much of it. And there are fields that you literally have no need for,” says Trinidad. So for take two, she pared things down. “I just needed gender, birth date, parental status, race. I needed veteran status and disability status. And then I needed tenure and department. Those are the eight fields I needed to build a dashboard that could give me a meaningful narrative.”

Then there are fields that you don’t need. “This is a really long list, so take note: name. Just name. Name is the only field to exclude because you don’t want to associate any of the information with an individual person. It’ll look like — and can lead to — discrimination, and you can get sued,” says Trinidad. “If you export data and there’s a name included, just trash that pull right away, redact the name and export again. You don't want to work with any dataset that has 'name' explicitly, because you don't want to be in a situation where you get audited and you're looking at diversity in a data set with names it.

“Name” field aside, Trinidad winnowed the list of fields down by working with other D&I leaders as well as Lever’s Director of Recruiting and VP of People. This approach helped her extract just the categories that would be important to Lever — and its future. Once you find and organize the right data, it’s time to manipulate it to understand the story it tells. You may need to play around with various queries to discover which are most revealing. Here are a few ways Trinidad cut the data that was valuable:

Hires by month by team. “My favorite cut of the data was hires by month, by team. That really showed me how recruiters were faring against our diversity and inclusion strategies,” says Trinidad. “It also showed me how their recruiting climate worked.”
Hires by month by race. Take hires by month another direction, and your data will likely surface not only your org’s internal biases but also their interplay with your industry’s hiring cycles. “Say a given department hired 15 people, and ten of them were white. Then that’s something that we really need to be paying close attention to. We need to ask why,” says Trinidad. “One takeaway was that if the company wanted to hire new grads from diverse backgrounds — people who live outside the Bay Area, or who may not have considered tech careers previously — they needed to start the recruiting process much earlier. We acted on this takeway by changing our policy on relocation and by listing our open roles on job boards at historically black colleges.”
Hires by tenure. Start dates and end dates can yield a wealth of information, too. “What's the average tenure per people manager, and why?” There may be feedback in those numbers more powerful than anything you’ll get from an exit interview. “Are there growth opportunities for those people managers that are being missed?” Look for trends along other lines, too: gender, race, parental status. “When you understand whether there is a trend behind why people leave, you can work on that as soon as possible.”

How can one unveil these insights? Choose your tool for comfort over firepower. Making hiring data easily searchable empowers you to look at your numbers in revealing new ways, like drilling down to subsets of teams or specific backgrounds over time. “How you crunch the numbers is far less important than what you’re crunching,” says Trinidad. “Use whatever software feels most comfortable. I’m a fan of Excel, but others may prefer Google Sheets or even Docs. When you choose, give careful thought to how you visualize your data, as that will determine how quickly and comfortably your colleagues can engage with it. I use Tableau, but Excel can go a long way in making data digestible with charts and graphs.”

D&I leaders won’t always be able to interpret what the data is saying on their own, though. Lever’s Director of Recruiting stepped in and helped Trinidad understand the narrative behind many hiring stories. Because while your dashboard is a crucial tool, reviewing it with the relevant stakeholders is what makes it invaluable.

To formalize those conversations, Trinidad established a monthly meeting with hiring managers and their recruiters, as well as the Director of Recruiting and the VP of People. “Those check-ins are designed to be mutually beneficial. I learn what’s happening on the front line, and those who manage hiring everyday get updates on our D&I efforts as we hire across the company,” says Trinidad. “It helps recruiters feel like I’m working with them, not working against them. I’m not looking at them to solve all the problems, but really working alongside them to monitor each of their hires.”

By and large, when Trinidad meets with colleagues, she receives the same two questions, especially when the data shows a bias toward one group. Here is how she answers them:

Where's this data from? “This is from our HRIS. Once you become employee you elect to share this information with the organization. So we collect this right from our employees”
Okay, so how am I impacting this? “Chances are you might have been a hiring manager on one of these panels. Or you might've been the deciding factor for one of these hires. Now, please know that not one of these hires is terrible. I'm not saying at all that we ‘lower the bar.’ But what we need to do is be aware. To do that, we need to introduce metrics that show and help us understand our biases. We can see here, we're outrageously biased. Completely okay because this is a big problem industry-wide, but our hiring managers didn't know it was happening here. Without me sharing this, they had no idea where their biases might be affecting the process.”

Following those meetings, leave the team with a takeaway that they can review — and even return to. “Send them a snapshot of the meeting via email, with a screenshot of the dashboard that you went over and specific talking points in bullets,” says Trinidad. “Just don’t make email communication your primary vehicle for reviewing this data. There’s gold to be mined in the in-person conversation.”

That being said, part of instilling a culture of problem-solving is fostering a culture of data-mindedness. Make these numbers accessible, and encourage anyone involved in hiring to dig in. Trinidad even has dreams of spinning up a server dedicated to sharing diversity dashboards internally. However you do it, the goal is to get the whole team identifying — and solving — these problems.

“I knew that these efforts were taking hold when other company leaders started asking 'the whys.' When they would say, ‘Hey, I saw this and I think that this is interesting. What do you think?’” says Trinidad. “The swap to where they're asking you questions instead of you asking them questions is a fantastic indicator that things are really sticky.”

CREATE A CULTURE OF OPENNESS

As with any change management, you want those in a leadership role to feel a sense of ownership — that is also true of your diversity goals. First, they may need to admit that this is all new and unfamiliar. “At one point during my time at Lever, one of our employees admitted to me that he did not know a lot about this,” says Trinidad. “That felt like a huge stride, because it's really hard — in tech and especially in a startup — to admit that you don’t know what you’re doing. Especially when it comes to something as sensitive as diversity and inclusion.”

When you get that kind of candor, embrace it, and meet it with education. As you broaden the team working toward your diversity goals, you’ll also affect a crucial culture shift. Fully realizing this culture shift means encouraging that same candor from everyone on your team. “Once people saw that they could be comfortable saying, ‘Well, we're currently 6% black,’ and that wasn’t something that we whisper — once leaders understood what it meant to talk about that in a way that felt safe to them — I knew this shift had traction,” says Trinidad.

For many people, diversity and inclusion is very private. Part of my job is to show them that these aren’t things that have to be discussed behind closed doors. That becomes a signal that they can speak about their stories openly and authentically.

Often, the most important thing a D&I leader can do is describe their role and how they can help, then simply make themselves available. “I explain the ways in which I can help, and then let people come to me. Here’s what I say: ‘I’m happy to connect about your goals and help you think through where you want to go next. First, I need to understand your intention. Why is this important to you? It’s ok if you’re not sure why just yet, but we need to start there. We need to start with intention,’” says Trinidad. “That creates, I think, an instant feeling of safety. I’m not targeting you; I'm really looking to better understand your story and help in whichever way I can.”

Remember, though, that a feeling of safety is not irrevocable; it must be maintained. Creating a culture of openness around D&I also means taking the time to get everyone on board when you take action — a lesson that Trinidad learned the hard way.

“Right when I started, we tried to implement gender neutral bathrooms. And it did not go well. In retrospect, I didn’t solicit input from enough people,” says Trinidad. “I had several voices in my ear, but not necessarily the voice of the collective. So, we didn't have an issue because people didn't want folks to be able to use the restroom wherever they needed to. It came down to people feeling like a decision was made without them having the opportunity to weigh in.”

From that painful misstep, Trinidad gained a crucial insight: to successfully implement any D&I initiative, you have to start with the why. “Why is it so important? Who do I think this is going to help? Then the last thing is, how do I bring people along with me? How do I make sure that everybody understands this is what we're doing, and why?” says Trinidad. “The next step is to share them out, tell everyone why we’re doing this. Tell everyone what is means and how it will impact the business. Mostly, talk through how this will help to cultivate a culture of inclusion. People want to help, they want to be more accepting, they need to understand why.”

BUILD OUT YOUR D&I TEAM

By now, you may be convinced of the value — to your bottom line and your team’s culture — of prioritizing diversity. But particularly if you’re in the early days, it’s often unrealistic to dedicate headcount to D&I. Trinidad’s advice? Start wherever you can. This isn’t an all-or-nothing pursuit.

“If your company doesn’t have D&I expertise just yet, that's completely okay. But you do have to start with understanding what matters to your employees and what matters to you.” That might be as simple as defining success, at this stage, as making people feel heard. “Fantastic, that’s a stride in itself,” says Trinidad. “Let’s talk about what success looks like when it comes to people being heard.”

When you do begin to dedicate employees to D&I, there are two primary ways you can go: hiring an expert or shifting the responsibilities of existing staff. If you’re considering the former, just be aware that you might be priced out. The reality is that there simply aren’t a lot of seasoned D&I professionals out there. “They could meet in a restaurant for happy hour. That's how small that group is,” says Trinidad. “In a field changing as fast as this one, it doesn’t take long for the right person to catch up. Frankly, what is phenomenal right now might not work six months from now.”

Grooming a D&I Lead Internally

To Trinidad, experience is often less important than having enthusiasm and drive to do the work. As an organization, that can mean nurturing a groundswell. “At Lever, D&I initiatives were started by a task force — being a member of that taskforce gave me fantastic insight into how build inclusive cultures. Its members included folks in recruiting, engineering, sales and marketing. It was everyone. A lot of the foundation of the work I’ve done has come from that task force and the people in it,” says Trinidad. “If Lever hadn’t given me the opportunity to work on D&I despite not having formal experience in it, I wouldn't be where I am right now. It's completely okay to find someone who's passionate about D&I, and also has a programmatic mind to run these initiatives, and let them try it. That’s a type of diversity, and it’s a way you can change the way you’re thinking about your organization,” says Trinidad.

Just go in with a clear head and realistic expectations. You won’t get everything right at the outset. “In my first year in this role, I made some huge mistakes,” says Trinidad. “And the thing that helped me come back from those mistakes was knowing that I had the support of my team. I was doing this for the first time. It's okay to screw it up.”

Few startups have the resources to dedicate a full position to D&I, and that’s okay, too. “Let's say that you have an organization of fifteen, and three people are really passionate about getting this work done,” says Trinidad. “If each of them make it even 10% of their job, that’s 30% of a full-time person thinking about these problems. That's more than zero, and that's completely okay.”

But Trinidad is emphatic about one thing: pay them for that work. Not doing so is one of the most common mistakes she sees startups making, and it’s a culture killer. Either make D&I work a formal part of the interested party’s portfolio, or compensate them for their additional work. That doesn’t have to mean a salary change; it can be as simple as a bonus.

“If you don't have the ability to hire someone full time into that job, that’s fine. But show the people doing this work that it’s valued. There's nothing more debilitating than knowing that there are several tech organizations right now who have people doing this work on a voluntary basis,” says Trinidad. “They do not pay them for the strides that they're making. It will literally destroy your culture if your employees feel like your D&I initiatives have been built on their backs.”

When it comes to building a homegrown D&I team, there’s just one person who should be off limits: your HR leader. “If you conflate human resources and diversity and inclusion, you immediately set up a conflict of interest. My longstanding joke on this is ‘It's HR's job to protect the company. It's your D&I person's job to protect the people,’" says Trinidad. “That’s not to say that they’ll always be at odds — no doubt, HR and D&I will often need to collaborate. But their respective responsibilities are too incompatible to be combined. HR may be focused on areas such as compensation, benefits and recruiting. D&I is thinking about the things you’re bringing into the organization from home, the cultural appropriation you’ve had to deal with, the fact that you’re a single mother.”

HR is responsible for protecting the employees of a company as employees. Your D&I person is there to protect them as individuals: as people, as their authentic selves.

Hiring a D&I Professional

When it comes time to look outside your org to fill these roles, be aware of your biases here, too. In Trinidad’s experience, strong D&I leaders might not fit the profile you think. “They aren't always your activists. They aren't always the loudest voices in the room. They're people who can think critically and build really fantastic programs,” she says. “Because like all other programs, diversity initiatives are about setting goals, meeting deadlines, and, most importantly, understanding what success looks like and how to achieve it.”

Trinidad has two favorite questions to suss out whether a candidate has the right mix of project management skills and interpersonal maturity to handle this sensitive work:

What's something about Diversity and Inclusion that scares you? Look for an answer that’s honest and reveals the candidate has thought about what this work entails — anything but the pat “I don’t know a lot about it.” “If someone asks me this, I'm going to show you that I’ve done some research. That there are things that are comfortable and uncomfortable to me,” says Trinidad. “I might start by saying ‘Hey, I don't know a lot about what it means to be a parent in the workplace. And that's something that I feel a little bit nervous about.’”
How can you make sure all voices are heard in the workplace? The importance of this mindset and skill became particularly clear to Trinidad following the 2016 presidential election. “A lot of people were very disappointed and a lot of people were very excited. How do you create a space where both of those things can live, at work? It’s a delicate balance to strike — one that could invite discrimination concerns if handled badly — to accommodate such strong competing emotions within an organization,” says Trinidad. “There isn’t one specific answer to look for from candidates here. Can they articulate if their past workplaces felt more ‘open’ or ‘closed?’ If not, can they describe how they’d go about making that assessment?”

Along the way, assess each candidate for approachability, too; alongside a critical mind and program management chops, that’s the D&I leader’s most valuable asset. “You can't have a diversity and inclusion professional who isn't approachable to your employees, because then they are never going to raise things that they want to work on, or build trust with this individual.”

To really be successful in building your strongest, most diverse team, you first need to believe in why you’re doing it. The key there is having a personal — not pat — answer to why you want a more diverse and inclusive workforce. Become an avid consumer of your organization’s hiring data. That will not only require scheduled check-ins with your head of recruiting and hiring managers, but also developing your own dashboard to track hiring data. Export it from existing systems and pare down the number of fields you’re tracking to a handful at a time. Whatever tool you use, select for ease of use versus firepower. It’s as important that others can access and understand the data as it is that you can. That’s just one step in creating and maintaining a culture of openness — one where it’s okay for leadership and teams alike to talk about what needs to be improved. Finally, build out your D&I team, whether that’s bringing on a seasoned professional or grooming someone from within your organization. If the latter, rest assured, it can work. It’s where Trinidad started and she grew to define and drive change in her organization.

“For a long time, I think, people assumed D&I professionals were only social justice captains. And sometimes, especially for allies, that's not approachable. That feels intimidating and scary, because they don't feel — and I'll use specific language — woke enough. Anyone you entrust with this sensitive role needs to be wildly empathetic. They have to be willing to look beyond their own experience to say, ‘I understand that there are many sides of the different identities that need a seat at the table,’” says Trinidad. “One of those identities might be somebody who doesn't know a lot about diversity and inclusion. And that's okay, too. Don't make it a secret club. Don’t create the impression that if you're woke, you can talk to me about it. Build a company that says, ‘If you don't know anything, awesome. If you know everything, chances are you don't. But let's talk. Let's hash it out.’”

Photography courtesy of Ciara Trinidad.

First Round Capital

Jun 18

Preparing & Executing a Board Deck

Jun 18

Choosing an Independent Board Member

Jun 18

Identifying and Integrating Independent Board Members

Jun 18

Diversity Won't Stick Without Inclusion

Jun 18

Startup Documents

There are four versions of the new post-money safe, plus an optional side letter.

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Postmoney Safe - Valuation Cap and Discount v1.1.docx48.5KB

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Pro Rata Side Letter.docx22.4KB

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UYD D&I Council

This is a recommendation from UYD (Use Your Difference) on structuring a D&I Council.

What makes a diversity council effective?

The diversity council must be intimately linked to both the overall diversity initiative and to the overall organizational business strategy. They also must work well as a team and value the diverse perspectives represented in their membership. To ensure the diversity council is appropriately formed and guided, the following principles must be adhered to:

Senior leadership must embrace and support the process
Clear delineation of roles and responsibilities
Thorough selection process to ensure the appropriate mix of skills
Representative membership
Effective teamwork skills
Appropriate infrastructure
Focus on trends and long-term change, not individual issues
Diversity must be linked to other organizational initiatives
Structured two-way communication with council
Adherence to these principles greatly enhances the likelihood of a meaningful, successful diversity council.

Proposed Role of the D&I Council

The role of the D&I Council diversity council serves as an advisory body to help senior leadership understand the complexities and nuances associated with diversity success. Although senior leaders often make decisions based on the lens through which they see the world, that lens is often skewed due to a lack of diverse representation. A diversity council can serve as the leaders' eyes and ears to help all the organization's diverse stakeholders experience the value of diversity. An effective council is also a visible sign to the organization that senior leadership is sincere about its commitment to diversity success. The council can serve to suggest actions pertaining to diversity success, gain insights from the members of the organization on their perceptions of the diversity effort, and monitor progress of the diversity initiative. The council will frequently sponsor events that help to celebrate diversity and further educate the organization on the importance of diversity to the success of the organization.

Formal Structure

Volunteer Representative Membership
Elected Diversity Council Officers
Diversity Council Mission & Vision (Proposed by council, should include company wide-input, and leadership approval)
Council Led Activities Calendar
Allocated Budget
Council Meeting Agendas
Council Communication Manual (For Newsletters, Memos, Emails, Flyers & Events - Should include approval process directives)
Develop strategies for:
Proposing Continuous D&I Education Efforts
Supporting recruiting & partnership events
Reporting Metrics

Activities of the D&I Council

Create an internal business case for diversity and set diversity expectations for seniormanagers
Lead efforts in defining what Diversity and Inclusion means to Spring (with companywide employee input)
Lead efforts in Diversity & Inclusion workshops
Establish affinity and employee resource groups
Institute required diversity trainings
Develop a calendar for the 2017/2018 reflecting diversity related events and themes
Work with HR to welcome potential new hires and refer potential candidates to therecruiting team
Establish events that help celebrate diversity and further educate employees in the company on the importance of diversity to the success of the organization
Work with leadership to formalize a process for diversity representation at the seniorlevel, and develop plans for establishing a mentoring program

Pitfalls

The diversity council is not the sole owner of the process. All organizational stakeholders must play a role in diversity success. Senior leadership, managers, human resources, employees and all others designated to impact the organizational culture should have identified roles in the diversity journey. The members of the council must openly and honestly represent their viewpoints; however, they should keep the organizational agenda as top priority while serving on the diversity council.

To avoid pitfalls impacting diversity success, the council must realize their role is not to:

Advocate for personal concerns related to issues of inclusion
Substitute for the critical role leadership plays in the diversity/inclusion process
Implement activities and programs independently
Act as the sole owner of the diversity process
Act as a "complaint body"
Make policy

To help avoid possible pitfalls, new members and non-members should be encouraged to attend

meetings, and council membership should be rotated every 12 to 18 months to ensure that fresh viewpoints and ideas continue to flow as part of the council efforts.

Officers within the Diversity Council

President

Ensures that the Diversity Council mission is executed.
Leads the Diversity Council officer team.
Sets meeting agenda and presides over Diversity Council meetings.

Vice President

Assists with special assignments as requested by the President.
Performs the duties of the President in the absence of the President.
Reviews all committee chair’s reports and activities.

Secretary

Maintains all Diversity Council records and ensures their accuracy. Performs all duties relating to meeting logistics, including conference calls.
Sends out meeting reminders one week in advance, including distribution of the minutes of the prior meeting.
Prepares and provides minutes of all Diversity Council meetings and conference calls.

Historian

Maintains and preserves the history of the Diversity Council (publications, scrapbooks,

etc.).

Election of Officers

The officers shall be elected by members of the Diversity Council
The officers shall serve a one-year term, and elected

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What We Learned from Improving Diversity Rates at Pinterest

https://hbr.org/2017/07/what-we-learned-from-improving-diversity-rates-at-pinterest

Juan Díaz-Faes for HBR

In today’s workplace, diversity is more than just a buzzword; it’s a way to build a stronger business. At Pinterest, we understand that diverse teams yield smarter, more innovative results, which are essential in the competitive, dynamic tech industry. With over 175 million active users worldwide, Pinterest thrives on providing users with relevant ideas: what to wear, what to cook, how to furnish your home, and where to travel. Pinterest’s fastest growing users are outside of the United States, and for current and future users, it’s important that the people building our product make it relevant to people of different ethnic, social, physical, and geographic backgrounds.

But businesses have long struggled to increase diversity across all levels. For nearly a decade, I worked at Catalyst, a nonprofit focused on helping women advance in the workplace, consulting with progressive companies who began investing in diversity initiatives in the ‘90s. The tech industry joined the diversity movement to diversify their workforces far later, after being scrutinized for its stark lack of gender and ethnic diversity. What brought me to Pinterest was a bold move I hadn’t seen previously: in 2015, the company decided to set public, challenging goals to increase hiring rates of women and employees from underrepresented ethnic groups.

For example, while women typically make up roughly 16% of software engineers in the U.S. (and almost no companies report engineering data specifically), Pinterest’s goal in 2016 was to hire women engineers at nearly twice this rate. The goal was based on a legal analysis of the current workforce, industry graduate rates, and co-founders Ben Silbermann and Evan Sharp’s desire to push far beyond the status quo after two years of flat data.

The next step was to figure out a strategy to reach these goals, and, more broadly, to ensure a culture of belonging and managerial competence in inclusion. I joined Pinterest as the company’s first Head of Diversity in January of 2016. By the end of that year, we had hit or exceeded most of our goals, improving hiring rates of underrepresented engineers from 1 to 9% and increasing underrepresented talent from 7% to 12% in other roles. But we saw limited movement for women engineers, only increasing our hiring rate from 21% to 22%, which fell short of our goal. While higher than industry norms, this flatness was in large part due to our focus on putting more women in senior roles versus in entry-level roles (more on that later). Over the course of my first year at Pinterest, I’ve learned four key lessons about how to improve diversity from within a company:

1. Setting diversity goals isn’t enough. You need (repeated) explanations of why they matter.

Rolling out public diversity targets is an important step, but achieving these goals requires intense and regular follow-up throughout the organization. It can’t just be left up to HR, either.

We learned we can make faster progress if hiring managers understand how diversity advances our goal of building a global, world class product. While I worked with the leadership team to digest and communicate research and stories on this, my team doubled down on efforts to engage hiring managers in inclusive decision-making. First, we instituted an unconscious bias training program for every new employee within their first two weeks, delivered by trained employees across all functions. The sessions give practical advice on how to disrupt bias in decision-making. We created a playbook and training for managers focused on inclusive leadership. These provide strategies on how managers can design more inclusive meetings, team experiences, and give consistent feedback — based on research that employees receive different types of feedback depending on their gender or cultural background. We also conducted an in-house study identifying the best practices of our most inclusive leaders, identified through team feedback. Our study found that these managers tended to empower their employees with ownership of their roles while also encouraging risk-taking; we’ve made the results available to the rest of our industry.

2. Embracing diversity means getting comfortable with being uncomfortable.

When I walked into Pinterest, one of my biggest concerns was gauging and navigating the adversity of those threatened by or dismissive of inclusion and diversity. In every company, there are skeptics — both silent and outspoken — who question whether diversity has merit. Others wonder if underrepresented groups can truly meet a high hiring bar. And because we put a stake in the ground regarding our goals, some have succumbed to zero-sum thinking, assuming that, despite our company growth, diversity programs in tech companies favor some groups at the expense of others.

Being clear about our goals and experimenting with new methods upfront helped break through some of the status quo. We found that people tend to refer job candidates who look like themselves, so we decided to ask people for loose connections and leads instead of referrals. This landed well only when we made it optional rather than required, and when we reminded people that these candidates would receive the same scrutiny as any other hiring candidates. (Although it should be assumed that no candidates will get special treatment, that needs to be restated frequently.)

Furthermore, different groups have unique concerns that need to be addressed separately. Senior women wonder if the company will truly put women in leadership positions — a valid concern — thus, we discussed embedding leadership targets within our hiring goals while relaunching our female empowerment employee resource group with strong executive sponsorship. Perhaps the most immediate impact was on our recruiters, who faced new sourcing and relationship challenges. My team and I worked alongside recruiters to ensure we would help them test new strategies for hiring. One example is our new apprenticeship program, which brings in new software engineers from non-traditional computer science backgrounds who are strong performers.

While I continue to manage different perceptions about these changes, I’ve found that being explicit about diversity makes employees keenly aware of underrepresented talent we haven’t taken the opportunity to connect with.

3. Diversity doesn’t slow down hiring — it makes it more efficient.

Last year, Pinterest grew from 700 to more than 1,100 people. In a young, hyper-growth tech environment, many managers are new and trying to pursue results quickly, without spending too much time on team building. This can lead some to make hiring decisions without considering a broader slate of candidates.

There’s a blanket misconception that factoring diversity into hiring automatically slows the process down, or in some way lowers the bar for new hires. In the long run, adding a lens of diversity to recruiting actually makes the process more efficient. Hiring from a diverse candidate pool has made us more thoughtful and deliberate about where we look for candidates, allowing us to look beyond the people that come to us via networks (e.g. referrals).

For example, when trying to hire senior roles, we began ensuring that we had at least one woman and one underrepresented candidate in the final candidate pool. This resulted in our highest diversity in executive roles to date — and our first ever executives from underrepresented groups in their fields, including our first woman as Head of Engineering. And instead of interviews assessing vague notions of “cultural fit” that we know can activate inherent biases, we trained employees on consistent interviews that focused more on qualities we value in Pinterest employees, like problem solving skills and curiosity.

4. Pursuing diversity requires plenty of course correction.

Like any new effort, many well-intentioned ideas can end up with unintended consequences. For example, studies have shown that removing names from resumes to prevent discrimination can actually have the unintended effect of evaluators making biased decisions based on other cues.

For us, we missed our aggressive 2016 goal of 30% of newly hired engineers being women. While this was a setback, we learned something invaluable halfway through our efforts: our original goal was too broad. Although the pool of entry-level talent is more diverse than that of tenured engineers, we realized that we couldn’t just increase the number of junior women engineers — we also wanted to make sure that women engineers were well represented at every level of the company. When speaking with our current female engineers, we learned that having more women at the top would lessen stigmas linking women to junior positions. That’s why we decided to focus specifically on hiring senior women later in the year, a much smaller but vital talent pool. After revising our internal goal to capture more senior women, we were able to focus the remainder of 2016 on bringing in experienced senior women engineers, including our Head of Engineering.

There is no playbook for making every employee feel included. In a sense, we’re all writing it together right now. We continue to work on creating a sense of belonging for every employee at Pinterest through events, discussions, and employee groups that build community and involve our executives. We’re still working to upskill our managers on inclusion, with trainings and team-specific discussions, and to determine real incentives for being an inclusive ally. With the above lessons in mind, our company is attracting people who know where we stand on diversity and the value it brings to our product. They are coming because they believe in it, too.

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On Investor Updates— Why they actually matter.

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SAFEs

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How to Make Tech Interviews a Little Less Awful | by Rachel Thomas | Medium

https://medium.com/@racheltho/how-to-make-tech-interviews-a-little-less-awful-c29f35431987

Everything about the current interview process in tech is broken. I suspect that, no matter what, being evaluated and making judgements on others for a decision that has a big impact on you both is never going to be fun — especially since both of you only have a limited amount of time for the process. However, I think there is plenty of room to make tech interviews slightly less awful than they currently are.

The dreaded white-board interview! Photo from #WOCinTech chat

What is your goal in interviewing candidates? If you answered “to hire the best candidate” you should reconsider. Forming the best team is a goal that will better serve your company. Will finding candidates with the same strengths and same background as yourself add a lot to your company? Or might these similar candidates also have the same weaknesses, same blind spots, and same skills gaps that you have? What research on team performance should you be using when deciding who and how to hire?

A team of CMU and MIT researchers published a series of studies in Science showing that the smartest individuals did not result in the smartest teams, and that individual IQs did not map directly to the collective intelligence of a team. The smartest teams had the following 3 characteristics:

members contributed more equally rather than letting 1 or 2 people dominate
members scored higher at reading complex emotional states from people’s faces
had more women. That’s right, having more women on a team predicted that the team would perform better.

Even if you could gather a team consisting of only those mythical “10x rockstar ninjas,” it would perform worse than a team of qualified women who are good at reading emotional states.

So, what do we know about how hiring tends to work in practice — are companies behaviours in line with this research? The answer, as we’ll see, is 100% “no”!

Triplebyte, a technical recruiting company, conducts technical interviews and then sends the best candidates on to interview at the most prestigious startups. They have collected extensive data, both from over 300 technical interviews and how those candidates fare in earning job offers. The #1 finding from Triplebyte’s research is that “the types of programmers that each company looks for often have little to do with what the company needs or does. Rather, they reflect company culture and the backgrounds of the founders.”

Triplebyte’s key advice for job seekers is to read the bios of founders and apply to companies where the CTO shares your background. Since only 3% of VC funding goes to women and less than 1% goes to Black founders, this advice will be hard to follow for applicants from underrepresented groups or with non-traditional backgrounds. How rare is it for a founder to think that a Black woman candidate reminds him of himself? Before you suggest that the solution is just for women and people of color to found more companies, remember that investors prefer ideas pitched by a man more than an identical pitch from a woman, and that out of funded companies, those with a Black women founder raise an average of just $36,000 compared to an average of $1.3 million for companies founded by White men.

Photo from #WOCinTech Chat

People think that being smart means knowing the same things they know. Interviewers don’t realize that they’re bad at judging how much a question tests intelligence and how much it tests non-essential familiarity with particular concepts from the interviewer’s expertise. For crafting interview questions, this means that you must get an engineer with a very different background from the person who created a question to vet that question and confirm how difficult it would be for someone without a background in [insert non-essential framework or concept].

I was once on a team where the manager frequently ignored the team’s feedback from interviews to unilaterally make hiring decisions. The only pattern I could find was that he liked candidates that were similar to himself, and had a demoralizing effect on team morale to have our feedback ignored.

Powerful voices in tech have given the advice to “avoid false positives” (accidentally hiring employees who turn out not to be good) at all costs, even though this will result in more false negatives (accidentally rejecting candidates who would’ve been great). Steve Yegge, senior staff engineer and manager at Google for 11 years, writes, “Google has a well-known false negative rate, which means we sometimes turn away qualified people, because that’s considered better than sometimes hiring unqualified people. This is actually an industry-wide thing, but the dial gets turned differently at different companies. At Google the false-negative rate is pretty high.” Max Levchin, cofounder and former CTO of PayPal, says of the early days of PayPal, “There are some legendary-ish tales of me not hiring people because they used the wrong word in an interview… I’m sure we had lots of false negatives, but we have very few false positives.”

Joel Spolsky, cofounder of Stack Overflow, echoes this advice, adding “if you reject a good candidate, I mean, I guess in some existential sense an injustice has been done, but, hey, if they’re so smart, don’t worry, they’ll get lots of good job offers.” This would be reassuring if false negatives were random and nobody experienced more than a few. However, if an entire industry’s interview processes are biased against a particular group of people, members of that group will have a hard time getting hired anywhere, regardless of how talented they are. Consider false negatives in the light of the following two stories about the job searches of a Black engineer and a trans engineer.

Justin Webb, a software engineer with a decade of experience, who had just graduated from Hack Reactor (the most selective coding academy, and one that boasts a 99% job placement rate) was the only Black student in his class and the only one who couldn’t find a job within 6 months of graduating. Webb describes his interview process at GitHub as typical of what he faced at many companies. At one point, what he believed to be the final interview for the job turned out to just be the 4th round in a 6-step process. Github eventually rejected him, saying that they didn’t see him as a good fit, despite his having passed their most recent interview challenge. “If the way I passed the test wasn’t right enough, I could’ve learned the right way to get the answers right,” Webb said. “But hearing ‘right’ wasn’t right enough was frustrating.”
February Keeney, an engineering manager at GitHub and a trans woman, writes “my career has become an A/B Test in gender. With the clear ‘winner’ being male.” For the first 15 years of her career in tech, she presented as male and received an offer every single time she had an on-site interview. After she transitioned, she spent a year job searching, receiving numerous rejections. Keeney reports that mid-transition, “Finally, one day, I gave up. I went to an interview without nail polish, no lip gloss. I presented as male as possible. Lo and behold: I got an offer.”

Keeney recounts, “On a couple of occasions, I noticed a clear antagonistic shift when the interviewer realized I was trans. The questions got unfairly difficult and the tone more deeply interrogatory. It is not hard to ensure a candidate does poorly on an interview if you are really determined to undermine them.” She writes of the frustration of interviews that went well, where there were multiple rounds and onsites, and then finally at the end she would be rejected based on something that was discussed as a non-issue in the very first phone screen.

It’s easy for Spolsky to say that false negatives are not a big deal, but brutal for Webb or Keeney to endure a discouraging 12 months of job searching, receiving surprising rejections after interviews that went well. Companies with biased interview processes are not aware of how many great Black, Latino, and trans people they are rejecting who would have made excellent employees, and everybody is losing out.

Photo from #WOCinTech Chat

If at all possible, track the people that you reject to see if any of those rejections were false negatives. Trek Glowacki, a software engineer at marketing startup Popular Pays, wrote “I’ve been twitter following the careers of people we interviewed but passed on at my last gig. Turns out we were almost always wrong. We had a group called ‘Bar Raisers’ who mainly torpedoed candidates that lacked ‘CS Fundamentals’. We passed on so many good people”.

Marco Rogers, an engineering manager at tech startup Clover Health, aptly pointed out “Sometimes the reality of privilege is as subtle as a lack of extra scrutiny when you’re trying to get a job”.

It is common in tech for interviewers to all have their own pet interview question, and for each candidate for a position to be interviewed by different sets of interviewers, thus receiving different questions. At many companies, interviewers produce a simple binary hire/no-hire vote (as opposed to gathering data across several criteria). Some of the interview questions may have little, if anything, to do with the day-to-day work required for the position.

Your interview process should follow the following four simple guidelines:

Resemble actual work the candidate would be doing in their job
Clear rubrics
Consistent and standardized
Don’t have an elite-candidate fast path

Let’s look at each of these in more detail.

Resemble actual work the candidate would be doing in their job.

Developer Yegor Bugayenko (the author of a highly rated book about object oriented programming) writes about the huge waste of time it was when Amazon flew him out for an interview that consisted of 4 hours of whiteboarding algorithm questions. If the recruiter had said, “We’re looking for an algorithm expert,” he would have declined and both he and Amazon could ha’ve avoided wasting their time. “Clearly, I’m not an expert in algorithms. There is no point in giving me binary-tree-traversing questions; I don’t know those answers and will never be interested in learning them,” Bugayenko writes.

Photo from #WOCinTech Chat

Thomas and Erin Ptacek, formerly founders and principals at Matasano, suggest constructing a test for a web developer position by taking an application you’ve written, removing some features (such as search or the customer order update), bundling up the app with all its assets onto a virtual machine, give it to the candidate, and have them add back the feature you removed. Popular communications app Slack has built an engineering team that is more diverse than many other tech companies, and Slack Director of Engineering Julia Grace describes a similar process of a real world coding challenge as part of the Slack engineering interview. Although Matasano and Slack give these challenges as take-home assignments, I think they could also work as part of an onsite interview [see the next section for the take-home debate]. For instance, the Airbnb data science team gives candidates a project to work on during the onsite, in which they have a few hours to work by themselves but can ask questions of the team during this time.

Lever, a tech start-up that builds popular recruiting software used by Netflix, Reddit, Yelp, and Lyft, describes mock code reviews as a key part of its own interview process for software engineers. Lever engineer Zach Millman writes, “Problem-solving and getting things done are important, but ideally we’d also hire engineers who are great at API design, naming, testing, maintenance, scaling, extensibility, etc. — all of those unglamorous things that actually make software projects successful and sustainable” and that mock code reviews are designed to get at these values. Importantly, mock code reviews assess a candidate’s communication skills and prioritization.

Clear rubrics

Research has found that the less well-defined the criteria for a hiring decision, the more that bias and post-hoc justifications play a role in decisions. A study by Yale researchers titled “Constructed Criteria: Redefining Merit to Justify Discrimination” found that when a male candidate had more practical experience and a female candidate had more academic experience, people chose the male candidate and ranked practical experience as more important. However, when the roles were flipped (the man had more academic experience and the woman more practical experience), people still chose the male candidate and instead ranked academic experience as more important. This effect was mitigated by forcing people to decide on their criteria before looking at the applications.

Elena Grewal, interim head of data science at Airbnb, identified that women were being disproportionately weeded out during the take-home exercise part of the interview process. “We took a close look at this and realized that the people who were grading the exercise had no clear rubric, so we changed this and made it clear what we were looking for, we made the grading consistent, and if a person was successful they were moved to the next round.” Since instituting that change, the percentage of women on the data science team has doubled from 15% to 30%.

Slack’s exercise is graded against a set of over 30 predetermined criteria. As discussed in the Yale study above, deciding on a clear scoring rubric before evaluating candidates reduces bias. The Ptaceks recommend collecting as much data as possible, and that this data be objective facts, such as: unit test coverage, algorithmic complexity, and handling a known corner case.

Consistent and standardized

Every candidate should receive the same test, be asked the same questions, and should be graded in the same way. One way that Slack further attempts to remove bias and standardize the results is by hiding the name and resume of the person submitting the test from the grader. (Reminder: resumes with traditionally African-American names are viewed more negatively than resumes with stereotypically White names, and job applications with female names are viewed more negatively than job applications with male names).

Photo from #WOCinTech Chat

To reduce bias, tests don’t just need to be graded consistently; the entire process of evaluating a candidate needs to be consistent. Professor Lauren Rivera of Northwestern’s Business School “played a fly on the wall during hiring meetings at one consulting firm. She found that the team paid little attention when white men blew the math test but close attention when women and Black people did. Because decision makers (deliberately or not) cherry-picked results, the testing amplified bias rather than quashed it.”

Don’t have an elite-candidate fast path

It’s valuable to know what your tests say about a candidate you know you want to hire. Seeing how your elite candidates perform may help you discover that some of your tests/questions/criteria aren’t useful. An HR director at a food company discovered “that white managers were making only strangers — most of them minorities — take supervisor tests and hiring white friends without testing them.” Hiring through the friend networks of current employees is one of the primary ways that tech companies recruit, and there can be a lot of variation in interview experience depending on who at the company you know and how well you know them. Given that three-quarters of White people have no non-White friends, we can guess the race of most referrals in tech companies with predominantly White employees.

We often mistake confidence for competence. Women perceive their abilities as being worse than they are, whereas men have an inflated sense of their abilities. This difference causes groups to be more likely to pick male leaders because of their over-confidence, compared to more qualified women who are less confident. Tech interview practices lead us to rate confident candidates more highly than less confident candidates. The solution is not just to tell women to be more confident, because women are perceived negatively for displaying traits associated with confidence in men (negotiating for themselves, speaking more in meetings).

No. Performing under adversarial pressure from co-workers is not inherently part of the job of being a developer. Even for positions that would involve frequent on-calls or racing to fix failing production systems, developers can be a collaborative team uniting around an external issue, not adversaries against their fellow co-workers. If your company has a work environment of adversarial competition or hostility, you will have trouble retaining and attracting employees and should rethink your culture.

Even the best interview process in the world will not be enough to overcome a biased or toxic culture. This is not just a theoretical issue — even a year before the most recent revelations about Uber’s toxic culture, engineers were sharing on Medium the responses they send to recruiters declining to even interview with Uber (see Tess Rinerson’s Dear Uber Recruiter and Tara Adiseshan’s Dear Uber Recruiter Part 2, both from March 2016). Note that it is not just Uber — there are many, many companies losing applicants as women warn each other about their experiences with toxic companies.

Photo from #WOCinTech Chat

This is a highly contested question and there are reasonable arguments on both sides.

One of the primary concerns about work sample tests is that they can be very time-consuming, which puts people with less time (parents, those caring for elderly or sick relatives, people with health challenges, or anyone needing to work multiple jobs) at an unfair disadvantage. On the other hand, given that any recruiting process must by definition take up a significant chunk of an applicant’s time, the flexibility of a take-home assignment can be the best option for many. Furthermore, it’s likely to more closely reflect the real work that an applicant will be doing, compared to white-board coding in 45 minutes with someone looking over their shoulder making comments.

If you do use a take-home assignment, you should:

Have a time limit (with candidates choosing when they will receive the assignment, and then agreeing to email it in 1–3 hours later) and don’t be too time-consuming. I once spent two consecutive full weekends on take-home coding assignments, while working full-time, and I felt so exhausted afterwards that I planned to take a month off from my job search (fortunately, those assignments eventually led to offers). And this was before I had a child!
Have a reasonable screen beforehand. It’s not fair to ask someone to do hours of work if there’s little chance you’ll invite them for an onsite. I feel angry when I hear about friends spending weeks on multiple take-home challenges (for a single company) and then being told that they don’t have enough experience. That is messed up! Companies should know whether a candidate has enough experience from the resume or initial phone screen, before wasting dozens of hours of time.
Consider paying candidates for time spent. I have the financial means to hire a babysitter for my toddler if I wanted to do a take-home assignment for a company that I was excited about, but not everyone does.
Realize that some people will choose not to apply. I’ve decided against applying to a number of companies once I realized how long or poorly constructed the take-home assignment was.
Consider giving people options, because personal preferences vary. I find pair-programming interviews to be the most anxiety producing (they make me very self-conscious), but many people prefer them. I enjoy whiteboarding because of my math background. If you offer candidates a choice, be sure to gather data and make sure that you are fair across challenge-type.

Both Slack’s engineering team and Airbnb’s data science teams make use of take-homes, and they are doing better at diversity hiring than most tech companies. However, these teams also have rigorously pre-defined criteria for grading, so perhaps that is the reason behind their diversity. Maybe the reason I love the Ptaceks’ blog post isn’t that they use take-homes, but that it is so infused with respect, thoughtfulness and consideration for the interviewee. Perhaps any interviewing format could work as long as it is thoughtfully constructed, involves consideration and respect for the interviewee (and their time), has clear criteria, is consistent and fair, and gathers data.

Hopefully, it is abundantly clear by now that if you want to increase diversity at your company, you will need to completely overhaul your interview process (and that if you don’t increase diversity, your organizational performance will suffer). However, the very first step to increasing diversity, which you MUST do before you do anything else, is to make sure you are treating everyone, including the women and people of Color who are already working at your company, VERY WELL. This includes helping them prepare for promotions, listening when they speak, and firing their harassers. Unfortunately, this is rare. You can read more here.

Interviewing is less fun than coding, and designing a thoughtful interview process is even less fun, but it is crucial that you put time into doing it well. Otherwise, you will not notice awesome candidates right under your nose, and your company is not assembling the best team possible. At most companies, technical interviewers receive no training, and interviewing is a thankless task, considered a distraction from real work. It will take more time than you are currently putting in to interviewing to start doing it better, and you need to appreciate your employees that do it well.

This post is part 3 in a series. Here is part 1 (about bullshit diversity strategies) and part 2 (about why women quit tech).

Jun 18

Using Current Investors to Develop Your Fundraising Approach

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1 “The DHM Model”

2 “From DHM to Product Strategy”

3 “The Strategy/Metric/Tactic Lock-up”

4 “Proxy Metrics”

5 “Working Bottom-up”

6 “A Product Strategy for Each Swimlane”

7 “The Product Roadmap” (current article)

8 “The GLEe Model”

9 “The GEM Model”

10 “The Quarterly Product Strategy Meeting”

11 “A Case Study: Chegg”

12 “Step-by-Step Exercises to Define Your Product Strategy”

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Introduction

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Pre-reading

Discussion recording

Additional resources

Ground rules for continuing courageous conversations

Four agreements:

Responsibility to each other and to the courageous conversation process

Becoming anti-racist: fear, learning, growth zones

Why be an inclusive leader?

Definitions from which we can all work for this discussion:

Small group discussion

Intersectionality

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Get the Knowledge You Need

Write an Action Plan

Act

Take responsibility for decisions.

Take responsibility for communicating.

Focus on opportunities.

Make meetings productive.

A meeting to prepare a statement, an announcement, or a press release.

A meeting to make an announcement—for example, an organizational change.

A meeting in which one member reports.

A meeting in which several or all members report.

A meeting to inform the convening executive.

A meeting whose only function is to allow the participants to be in the executive’s presence.

Think and Say “We”

Identify and choose projects that you can own from beginning to end, and deliver them

Establishing your leadership presence and visibility

Keeping engaged in and motivated by your work

Setting yourself up for success in the role and beyond

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America needs Paid Family Leave. Fathers need to use it.

Eligibility

Coordination with State Benefits

Benefit Plans

Return to Work

Initial interview email

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Go beyond the token moment

Design for relevance

Ask but do not assign

Consistency over intensity

Resources for Black History Month