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[ORG-012] HashiCorp Leadership Team Weekly Meetings and Quarterly Offsites Summary: Goals and format for weekly and quarterly HLT meetings Created: Jan 28, 2020 Status: WIP | In-Review | Approved | Obsolete

Owner: kevin@hashicorp.com Contributors: rcohen@hashicorp.com Approvers: dave@

Background This RFC documents changes to our operating cadence to follow a more consistent schedule each quarter. The desired state of the operating cadence relies on consistent HashiCorp Leadership Team (HLT) meetings on a weekly and quarterly basis to keep the company on target to reach its fiscal year goals. This RFC documents the goals and format for the HLT weekly meetings and quarterly offsites.

Proposal HLT has two recurring meeting types — weeklies and quarterly offsites. The weeklies are every Monday at 1:30pm PT. The quarterly offsites are currently midway through the quarter, but will likely change in FY22 to be the fourth week of every quarter in accordance with the operating cadence.

HLT Quarterly Offsites

Goals ● Longform discussion on the top company challenges. These challenges are surfaced from product line, theater, and functional QBRs in week 3. Those QBRs review the state of the state and give the HLT insight into what is performing well and what needs support. ● Team building ● Fiscal year planning

Format - Q1/Q2 The format is slightly different by quarter since Q3/Q4 have fiscal year planning considerations

● Day 1: Discussions on key company challenges ● Day 2: Team building activity

Format - Q3 (planning starts) ● Day 1: Functional scorecards and headcount plan drafts due ● Day 2: Discussion on key company challenges

Format - Q4 (planning nearing completion) ● Day 1: Discussion on key company challenges ● Day 2: Headcount trading

HLT Weeklies

Goals ● Follow up on the action items from the HLT offsite to make sure we address the discussed challenges ● Once a month review progress on the key company priorities for the year. The 5 for FY21 are cloud, consul, land/expand/renew, leaders at every level, and company operating system. A monthly review ensures we keep these priorities top of mind. ● Highlight other strategic work across the company and give rising leaders more executive visibility.

Format ● 30min of guest presenters highlighting strategic work. This is usually two 15min sessions ● 30min of HLT action items review

Improvements ● More non-executive ownership of HLT action items. We need to make sure we're delegating work down into the organization and giving opportunities for growth. ● More data in our reviews and decision making. Scorecards are a good step in this direction and hopefully we can establish other mediums for reviewing company performance data.

Outline

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• Meeting Purpose
• Agenda
• Meeting Engagement
• Tactical Stuff.)

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• 1) Status update (for accountability)%20Status%20update%20(for%20accountability),This%20is)
• How Good Are Your Meetings?

The team at First Round did a great job compiling and sharing a list of questions for 1:1s that span five categories:

• 🤔 Self-reflection
• 🔍 Identify some topics
• 💡 Understand the issues
• 🎯 Develop long term goals
• 🙌 Deliver better support

Outline

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1. Icebreaker    build awareness of teammates’ personal context

2. Reflect   share anonymously what did/didn’t work, for you

3. Group   review Reflections and discover common themes

4. Vote   select which topics deserve the team’s attention

5. Discuss   create an action plan for how to improve

The team at Lighthouse has great content for building leadership skills. Here's their take on 1:1 meetings.

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• Part 1: The benefits of one on one meetings

• Their real value to managers

• The value to organizations

• Problems they help overcome

• Part 2: The one on one meeting template great leaders use

• Step 1: How to prepare for one on one meetings like a pro

• Choosing the frequency to meet

• Logistics (When, where, length)

• How to tell your team about this

• Step 2: What to do in your one on one meetings

• Bring great one on one meeting questions to break the ice

• Topics to cover

• Making it actionable and accountable

• Step 3: Bridging the divide to the next one on one meeting

• How to build a rhythm

• Getting them involved & accountable

• Part 3: Advanced skills for your one on one meetings

• What great leaders don’t do

• Pro moves that level up leaders and their departments
• Using one on ones to help your team thrive in difficult times

Outline

• First focus on who is in the room.
• Make the meeting valuable
• Anything that can be done beforehand, should be
• Have a regular time for the meeting and hold it then every week

The Strategy team at Gemini: The strategy team at Gemini is a small team. There's seven of us; have this huge breadth of work. Everyone kind of has a vertical. 

How M&A is a part of Strategy at Gemini:

M&A is one of the pillars that we focus into, that we focus on in our strategy team…Many companies see M&A as a strategy, and are like ‘let's be strategic and acquire a company.’

M&A is essentially a tool that helps us facilitate and accomplish the strategy that we've set at the high level, it is not a strategy in itself…. M&A is not a magic bullet.

We see M&A as two different categories: strategic purpose, or for economic purpose. 

M&A doesn't solve your problems, it could theoretically solve specific strategy problems

The reasons a company may use M&A as a way to grow:

-product or infrastructure capabilities 

-talent 

-regulatory

-customer acquisition

-horizontal expansion 

M&A lessons learned:

Marshall: we've been quite successful with our M&A. And I think a lot of that is luck - we acquired good companies. 

[When acquiring companies] really dial in and get very honest and transparent with the principal of the target on what their role is going to be. Make sure that they are aligned. Make sure that internally you're aligned.

Why anyone at a company can help with an M&A deal:

Marshall: Even if you haven't done a deal, you can do a deal. If it's smaller company, it's easier. It's very much more an art than a science. As long as you have conviction on the target [company], build that relationship, get the conversation going, imply your intentions and see if it makes sense. 

The importance of maintaining company values through M&A

Cynthia: there is kind of an underlying theme throughout all of this, which is the importance of values. And especially when you're going through acqui-hires, the culture that you're seeing in the company that you're acquiring actually has a lot more weight than a lot of these more academic focused concepts that we talked about [today]…. We definitely think like that's not something that we should ever overlook, and that we should definitely focus on the relationship culture that we're bringing into into business for sure.

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Below is a summary of notes from Alexis Teixeira and Ben Spero about how CoS and BizOps leaders work together at Carta! This roundtable was produced in collaboration with our partner community, Chief of Staff Network!

Note: we tried to summarize the notes as much and as best as we could. Please refer to the video for details and more accurate information.

BizOps at Carta does four things:

1. Traditional business operations / centralized business operations team deployed out into projects across all the entire organization. This is really more project based work. 
2. Act as a service business lead for some of our new product incubation. Mini GMs for hire. As an example, if we want to try out a new idea, a new product, we don't want to necessarily hire externally. We want to kind of test this out with a dedicated engineering manager, product manager and then a business person. 
3. Our strategic partnerships team that also works with executive recruiting
4. Corp Dev that involves includes integration. So a lot of time, the corp dev team will go shopping, and then someone on the biz ops team will work to integrate the business.

Work as a CoS at Carta

Alexis focuses on three main buckets:

1. Executive optimization: Adding leverage to the Principal. Making sure that the CEO is focused on the right things every day. 
2. Stakeholder management: weekly leadership meeting, monthly board meetings, and quarterly board calls. Making sure that those are all planned and scheduled, and there are agendas, and everyone is prepared for those.
3. Cross-functional strategic projects: M&A, re-orgs, Board candidates searching, executive talent search, DE&I, future of work/return to the office, etc. This bucket she has the most overlap with BizOps team.‍

About Carta and BizOps: why operations is such a core part of our DNA is that we really took services businesses and turn them into software. So it was how do we optimize this service thing that's happening in the background to eventually make it a seamless software experience. 

BizOps team overview: There is a Chief Business Operations Officer who basically has 24 people reporting to him. And his five direct reports are basically kind of aligned to those five units mentioned above. 

How do CoS and BizOps work together:

Alexis: there's kind of like a push-and-pull element where sometimes it'll come from me, and sometimes it'll come from the Biz Ops team. 

Ben: Two ways I think about working with Alexis:  

1. I can work with her to help amplify something that I think needs more attention at the executive level. 
2. But then also comes from the other end, the CEO may say might say “Hey, you know, I think our product development used to be accelerating, I really just feel like it's slowed down the last six months. A: Is that true? And B, if that's true, I want to reorder the company, what should we do about it? ‍

One example of working together:

Alexis: Ben has worked on a couple of really interesting product launches. And because of that, part of the go-to-market strategy would be for Henry to reach out to other people to see if that resonated at all. And Ben and I would work together on kind of what that communication would look like. Making sure that we have like a draft list of people that we're working on together. 

Another way to think about BizOps:

Ben: our head of our group describes he says that we're basically the product manager for the business as a whole. And that means is that we are the ones if there is a something going well, or something going wrong, that we don't quite understand, we’re the ones who are tasked with basically figuring that out. 

How BizOps works on projects:

As an example, BizOps can diagnose the problem. Someone had an idea this was a problem, we then quantified how much of an issue that was.  Then we went to putting a plan in place to make sure that didn't happen again.

How BizOps can be a connective tissue to elicit feedback while also, you know, involving as few people as possible

On the Chief of Staff career path:‍

Alexis: what I do find to be interesting is I look at Ben's team (it’s makeup), and it's really like across the board in terms of backgrounds. And I think, interestingly enough, any one of the individuals on Ben's team would make an amazing Chief of Staff. Some of them have even become an off-shoot Chief of Staff. 

How Carta BizOps team could be different than other BizOps teams:

It is a bit more strategic. A bit more forward looking, rather than just metrics oriented. 

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A Lunch and Learn with Kard COO Katie Harper. She has risen the ranks at Kard over her 3 years there. Previously, she was also Head of Operations at Upwave. In this Lunch and Learn, Katie details she designs and implements operational cadence for herself and for the company. She literally walks through a table file, and details out how she thinks and maps out weekly, monthly, quarterly, and annually priorities.  

A few highlights:

• understanding work through “Urgent vs. Important” lens
• how business units are interconnected and how work/actions in certain areas create waterfalls and flows to other areas
• how Katie sees her role as a hole-filler and dot-connector given Kard is 30 employees
• the scorecard and overview that she creates, and how she thinks about sharing that in her company
• how Kard generally has one North Star metric and the business tracks into that metric
• how one department usually "leads" a company (e.g. product-led, etc)

Books recommended:

1. Good To Great by Jim Collins
2. High Growth Handbook by Elad Gil
3. The 80/20 Principle by Richard Koch

- as a team of one, you may be piecing together a handful of tools in the near-term, while hoping to create a larger system for longer-term 

- how widely used metrics like ARR can have different numbers across departments, creating later confusion and potential issues 

- the importance of company-wide definitions, and how it can take time and cross-company collaboration to determine them

- how hiring can be tricky. The combination of business acumen (strategy) and technical, data crunching hard skills is ideal… and some times can be rare to find. if you are that person, there can be room for you to grow 

- how some companies are trying to create a hub and spoke model across an org 

- always balancing “what is the best version of this metric? And how can I define and determine it and by when? 

- knowing where you want to go before you start. if you had all of the data that you could imagine, what would you actually do with it? Important to have an end in mind before you start looking and searching for data.

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Jonathan Mark, SVP of Business Operations & Strategy at Vestwell shares his top 6 points on how to build credibility followed by a Q&A!

Stephen Levin, Head of Business Operations at Zapier shares his thoughts on utilizing different frameworks (OKRs, MBR/QBR) to manage company objectives and organizational clarity around metrics.

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Stephen also discusses the approach they've taken at Zapier to build business operations as a function of the CEO and individual departments and how he's hiring operators at both ends of the experience spectrum (super junior & super senior) to balance the deliverables of his team!

A List of Over 200 Personal Values

However, it is useful to scan a core values list to prime yourself before the exercises.

And it’s beneficial to review a list of core values after you brainstorm your list to determine if you missed something important.

As a reference, here’s a list of 230 personal values:

Acceptance Accomplishment Accountability Accuracy Achievement Adaptability Alertness Altruism Ambition Amusement Assertiveness Attentive Awareness Balance Beauty Boldness Bravery Brilliance Calm Candor Capable Careful Certainty Challenge Charity Cleanliness Clear Clever Comfort Commitment Common sense Communication Community Compassion Competence Concentration Confidence Connection Consciousness Consistency Contentment Contribution Control Conviction Cooperation Courage Courtesy Creation Creativity Credibility Curiosity Decisive Decisiveness Dedication Dependability Determination Development Devotion Dignity Discipline Discovery Drive Effectiveness Efficiency Empathy Empower Endurance Energy Enjoyment Enthusiasm Exploration Expressive Equality Ethical Excellence Experience

Fairness Family Famous Fearless Feelings Ferocious Fidelity Focus Foresight Fortitude Freedom Friendship Fun Generosity Genius Giving Goodness Grace Gratitude Greatness Growth Happiness Hard work Harmony Health Honesty Honor Hope Humility Imagination Improvement Independence Individuality Innovation Inquisitive Insightful Inspiring Integrity Intelligence Intensity Intuitive Irreverent Joy Justice Kindness Knowledge Lawful Leadership Learning Liberty Logic Love Loyalty Mastery Maturity Meaning Moderation Motivation Openness Optimism Order Organization Originality Passion Patience Peace Performance Persistence Playfulness Poise Potential Power Present Productivity Professionalism Prosperity Purpose

Quality Realistic Reason Recognition Recreation Reflective Respect Responsibility Restraint Results-oriented Reverence Rigor Risk Satisfaction Security Self-reliance Selfless Sensitivity Serenity Service Sharing Significance Silence Simplicity Sincerity Skill Skillfulness Smart Solitude Spirit Spirituality Spontaneous Stability Status Stewardship Strength Structure Success Support Surprise Sustainability Talent Teamwork Temperance Thankful Thorough Thoughtful Timeliness Tolerance Toughness Traditional Tranquility Transparency Trust Trustworthy Truth Understanding Uniqueness Unity Valor Victory Vigor Vision Vitality Wealth Welcoming Winning Wisdom Wonder

Outline

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• What is “GTD”?
• The “in” list
• Processing the “in” list
• The “next actions” list
• The “waiting for” list
• Projects

• Contexts

• Agenda contexts

• The “some day/maybe” list

• Calendar

• Weekly review

• Trigger lists

• Getting it to work

• Tools

• Read/review folder

• Tickler file

• About this guide

Outline

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• 1 to 3 Employees
• 4 to 10 employees
• 11 to 30 Employees
• 31 to 100 employees
• 100 Employees
• 300 Employees and Beyon

Full details at the link!

Outline

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• Introduction
• Learn the (abridged) history of OKRs
• OKRs and Stretch Goals
• Bring OKRs to your organization
• Set objectives and develop key results
• Avoid OKR-writing mistakes
• Develop team OKRs
• Tool: Grade OKRs
• Update OKRs regularly
• Watch Google’s OKR presentation (video)

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• The role of the CEO: managing yourself
• Personal time management
• Delegate
• Audit your calendar weekly, then monthly
• Learn to say no
• Realize your old patterns of work can no longer apply
• Take vacations & time off
• Work on things you care about

Outline

• What is (and isn’t) an executive coach?
• How to find an executive coach

• How to choose an executive coach

• Interpersonal style & approach

• Sensemaking & application of theories
• Why are they an executive coach?
• Commitment to continuing professional development
• Do they have their own coach and/or mentor?
• Coaching qualifications
• Do I trust this person?
• Saying No

Outline

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• Spend more time on it.
• In the beginning, get your hands dirty.
• Look for smart, effective people.
• Have people audition for roles instead of interviewing for them.
• Focus on the right ways to source candidates.
• Have a mission, and don’t be surprised at how much selling you’ll have to do.
• Hire people you like.
• Have a set of cultural values you hire for.
• Don’t compromise.
• Be generous with compensation packages, but mostly with equity.
• Watch out for red flags and trust your gut.
• Always be recruiting.
• Fire fast.
• Put a little bit of rigor around the hiring process.
• Don’t hire.

The first 90 days are critical to establishing the right frameworks and relationships that will set up a Corporate Chief of Staff for long-term success. I interviewed 12 Chiefs of Staff to learn how they approached their new roles. While these Chiefs all came from different backgrounds, worked at companies of vastly different sizes, and had different expectations for their CoS role, they all followed some common tactical best practices.

Much of the corporate CoS role is about indirect influence, as the main working relationships for a CoS are typically not his direct reports. For a CoS, success in the role requires not only working well with one’s executive, but also having credibility across the senior leadership team (SLT) and with other employees.

This article is structured against two key goals and associated actions for achieving those goals. These goals are:

1. To establish trust and gain alignment with your executive
2. To establish trust and gain alignment with employees, both on the senior leadership team and elsewhere in the company

This article does not address what the CoS will do, but rather how the CoS should work.

Goal 1: To establish trust and gain alignment with your executive

Since the CoS role requires directly acting on behalf of your executive, there must be a high level of trust and alignment in both directions.

JohnMark Ludwick, a facilitator of the McChrystal Group’s 2019 Chief of Staff Summit, noted that a CoS must establish authenticated trust with one’s executive — essentially, layers of trust necessary for an executive to feel comfortable opening up when it matters most.

Action: Invest significant time with your executive upfrontAll the CoS’s agreed that you need to spend a disproportionate amount of time with your executive at the beginning of your tenure. This includes not just sitting in on as many meetings as possible, but also participating where appropriate, whether in the meeting or by taking next actions from the meeting. This is a prime opportunity to learn what your executive’s time is spent on, their communication style, and the dynamics of their key relationships.

The way in which this is executed will look very different based on a number of factors — such as whether you are in a new or established CoS role, whether you are an internal or external hire, the company size and stage, the company’s geographic scope, what industry the company is in, and how the company is organized. When Nika Shclover joined Token as CoS, she spent the first few weeks shadowing all meetings, both internal and external, just learning the business. The CoS role was specifically created for her, so this was an opportunity to identify areas where she might be able to contribute. On the other hand, Ben Winokur, CoS to the CEO at Passport, was at Passport for over 2 years in other roles before transitioning to the CoS role. While the CoS role was new, Ben had already established trust with the executive team, so they were comfortable working with Ben as a thought partner and strategic advisor right off the bat.

Action: Explicitly discuss your goalsSince the CoS role is not a standard role, it helps to have an early, explicit conversation about your professional development goals. You should also understand what your executive is looking to accomplish by having a CoS.

Richard McLean, CoS to the CTO at Elsevier, wrote a “user manual” for himself that he shared with his executive. The idea was not to explain what he does at work, but how he works. One of Richard’s values was to deliver outcomes and be judged on results, not activities. This value resonated with his executive, who himself wanted to be held accountable and who asked for open, candid feedback from Richard in turn. These user manuals are valuable not just to share with your executive but also with other colleagues. Richard has compiled several of these manuals here.

Carmen Collyns, CoS at Brex, joined as the 70th person at the company, helping them scale to 400 people across 4 offices just one year later. She supports Brex’s Co-Founders in a generalist capacity. When Carmen started, she made sure to ask them a series of questions upfront, including: “Where do you want to take this company?” and “What skills are you actively trying to improve?” This kept her focused and allowed her to clearly map her activities against these answers. [The full list of Carmen’s questions is at the end of this article]

Action: Learn each other’s working stylesThis is absolutely critical to having a successful working relationship. At McKinsey, we held a “team learning” at the beginning of every project to understand each team member’s working styles. Rather than assume others would know our communication preferences and quirks, we would simply tell everyone else what they were. They could be anything from “I prefer e-mail over voicemail” or “please cc me on all correspondence related to this workstream” to “on Tuesday evenings I am offline due to a family commitment”.

With your executive, this should also include a two-way conversation on how you both prefer to give and receive feedback. Should feedback be given real-time or weekly? Is it given in front of others or one-on-one? Many of the CoS’s had to routinely ask their executives for feedback; it wasn’t something that was regularly offered.

Leland Chamlin, CoS at Bowery Farming, shared that one of his interviews with CEO Irving Fain involved them getting into a 45-minute debate about something not related to Bowery Farming at all — the topic of what drives long term success in the music industry. One of the reasons Irving hired Leland was because Leland wasn’t afraid to provide feedback and push back.

If you do write a user manual, this can all be included there for discussion, and can also evolve as needed. Molly McCarthy, CoS at Insight Partners, suggested regularly monitoring your working style alignment.

Action: Set a communication cadenceFor the first two weeks, you should ideally sync with your executive twice a day — once at the beginning of the day and once at the end of the day. This may seem excessive but is critical to quickly aligning your priorities.

After that, you should establish a cadence of three types of meetings: daily check-ins, project review, and strategic brainstorming.

Holding regular alignment meetings with your executive are necessary in order to succeed in the CoS role

Your executive should be prioritizing these meetings, as they ultimately save time. If your daily check-ins are regularly cancelled then you should have a candid conversation to address the issue.

Tom Oliphant, CoS to Karen Peacock, COO at Intercom, has two 1:1’s with Karen each week. One is shorter to discuss more tactical items, and the second is longer to discuss broader strategic and long-term items. Carmen Collyns, CoS at Brex, found a slightly different rhythm with her Co-Founder. They also have two 1:1’s each week, but both utilize the same format where she can bundle and synthesize many updates, suggest next steps, and get approval. For higher priority items, they find the time wherever possible to communicate on these.

When I was CoS to Tony Hsieh, we learned that he was constantly getting one-off inbound requests from a variety of places. It cost him time to qualify each request — that is, understand what exactly someone was requesting, what resources they already had, etc. Tony realized he wanted to have the requests qualified and bundled so he could respond by type. Once we figured that out, I was able to aggregate and standardize the requests for him to review. He could then quickly go through each request and provide feedback.

Goal 2: To establish trust and gain alignment with employees, both on the senior leadership team (SLT) and elsewhere in the company

Since so much of the CoS’s role relies on informal influence, you need to have relationships with the SLT as well as with colleagues across the company.

Action: Explicitly communicate and demonstrate the purpose of the roleSince the role is still relatively new and can have many different iterations, you and your executive need to clearly communicate and demonstrate the purpose of the role to the SLT. Here are a few archetypes:

Enabler: Alice Lan, CoS at Opencare, came into the role when Opencare had grown rapidly from 25 to 50 employees within 6 months. Opencare hadn’t previously had a CoS Role, so her executive, Co-Founder Nik Bratkovski, had to set a clear understanding of the role for the broader organization. The leadership team initially saw Alice as a gatekeeper. She realized she needed to build personal relationships with them and demonstrate that instead, she functioned as an enabler. For example, Alice could help get high priority decisions in front of Nik, accelerating decision-making time from a week to a day. In order to do this, she created an “assertions document”, which walked through the key decision points for leaders and helped structure their thoughts. [Alice’s full assertion table is at the end of this article]

Counselor: Tom Oliphant, CoS to Karen Peacock at Intercom, was set up for success by Karen. Karen picked key influencers within the company to interview Tom for the role, so it was pre-socialized even before he began. After joining, he counseled business unit leaders behind-the-scenes to help them reach the best decisions.

Insulator: George Boyar, CoS at Mentor Collective, was able to insulate other functional heads from being disrupted. As new projects came up, he could take them on, leaving the functional leads able to focus on existing operations. If George ended up working on a project for more than a month, it was a signal that the work might merit an additional full time hire.

Connector: Given the CoS’s cross-functional view of the organization, it’s natural for the CoS to be able to look across teams and identify tactical ways in which people can be working together. Molly McCarthy, CoS at Insight Partners, was able to connect the right people at the right time, calling her job one of “mixing and matching”.

Problem Solver: Many CoS’s described being a catch-all for the leadership team. They were the first stop for new initiatives where it wasn’t clear where the responsibility would eventually sit. Ranika Kejriwal was the CoS to the Chief Product Officer at Tinder. She summarized her job as “problem solving — finding the root cause of an issue and figuring out a solution”.

Aligner: Charlie Joyce, CoS at OnDeck, shared an example of aligning meetings so subject matter experts could contribute their expertise in new ways. Often the expert was so entrenched in their area of focus that they didn’t realize their perspective might help another team.

Action: Rotate through multiple teamsIt’s important to get early exposure to all parts of the business. Rachel Lau was previously CoS at Via. She joined the company in December 2016 and immediately did a series of one-week rotations through their teams, including operations, data science, and customer service. In addition to giving Rachel a cross-functional understanding of the company, it also helped her build authentic connections. When new projects came up requiring cross-functional collaboration, such as real estate expansion, Rachel was able to effectively lead them due to her existing relationships across the company.

Finally, as a CoS, you must also establish trust and gain alignment with external parties, board members, and other stakeholders. Many of the tactical action items discussed in this article also apply to those stakeholders.

Thank you to the following Chiefs from the Chief of Staff Tech Network for taking the time to provide their insight for this article:

Alice Lan (Engagement Manager at Opencare)Ben Winokur (CoS to the CEO at Passport)Billie Solomon (CoS at Spin)Carmen Collyns (VP People Strategy at Brex)Charlie Joyce (Manager Strategic Initiatives at OnDeck)George Boyar (CoS at Mentor Collective)Leland Chamlin (CoS at Bowery Farming)Molly McCarthy (VP and CoS at Insight Partners)Nika Shclover (Co-Founder at Knight Bus, former CoS at Token)Rachel Lau (Treasury Go To Market Strategy at Paypal, former CoS at Via)Ranika Kejriwal (former CoS to the Head of Product at Tinder)Richard McLean (Director of Strategy & Performance at Elsevier)Tom Oliphant (CoS at Intercom)

Additional Resources

Questions from Carmen Collyns, CoS at Brex

• Where do you want to take this company?
• What are your values (personal and company)?
• Do you want to work on all things together, or delegate certain things for me to run with? Will I be a complement to you, or an extension of you?
• What are you bad at? What skills are you actively trying to improve
• What does a great day for you look like, and how could I help you achieve that?
• Do you have an Executive Assistant? (Answer must be yes as the CoS is not serving an EA role)

Assertion Table from Alice Lan, CoS at Opencare

Priority level: High/Medium/Low (remove all low priority from CEO scope)Leader: Person who needs CEO inputTime, Budget, Effort: Bullet points on time, budget and resources (remove anything under $X from CEO scope)Pros: 1–3 bullet points on why this recommendationRisks: 1–3 bullet points on any risks with this recommendationMitigations: 1–3 bullet points on mitigation plan for risksRelevant Links: Pre-read/financial model if relevantAction Needed: Input/Feedback/Brainstorm/Sign-off/Follow-up meeting

Join two robust Chief of Staff communities: the Chief of Staff Tech Network and the Corporate Chiefs of Staff Network

Read The First 90 Days: Proven Strategies for Getting Up to Speed Faster and Smarter (recommended by multiple Chiefs)

Read Paul Cohen’s 4-part series on the Chief of Staff role, including what to do in the first 6 months (recommended by Billie Solomon, CoS at Spin)

Outline

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• Product-User Fit: The extent to which you’ve built the right product for the right user.
• Power users are the biggest sign of product-user fit. Making the leap from product-user fit to product-market fit is about listening to these users to evolve your product to attract more users.

Homebrew has a ton of excellent and thorough guides. Their guide on Benefits is exceptional and covers the following topics:

• Where do I start?
• What's next?
• We're really small- what should we do?
• How much should the company cover?
• What kinds of plans can we provide?
• What's standard for benefits/holidays/vacation?
• How does unlimited vacation work?
• How do we measure success in benefits?
• What kinds of leave are there?
• How do we make this easy for our employees to understand?
• How do we support new parents?
• EAPs
• Gym Reimbursement
• 401(k)
• Meals and Snacks
• Insurance and Disability

Outline

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• Enter the Mission-Driven Team
• Saving Blockbuster

Outline

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1. First, the four major functions in a SaaS startup — Sales, Finance, Product, and Marketing — are all best run on a quarterly cycle.
2. However, it’s not the same cycle. Sales and Finance are on one calendar; Product and Marketing are on another calendar. I call these the Sales-Finance System and the Product-Marketing System.
3. If you snap these two calendars together, it will create a single operating cadence for the company.
4. Summary

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• State Granted Advantages
• Special Know-How
• Returns to Scale
• System Rigidity

SUBJECT:Follow Up from ____________

Dear ______,

Thanks so much for taking the time to apply to _____ . There were a high number of applications for this role, and unfortunately, there wasn’t a fit at this time. That being said, we really appreciate the time you took to learn about us — thanks again.

If there’s anything we can do to help with your job search, please let us know. And keep an eye on our website [Link to careers page], as we’re always updating it with new positions.

We wish you all the best!

Sincerely,

_________

Outline

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• What Is Priming?
• Types
• Process
• Real-World Impact

Outline

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• APPLYING PRODUCT DEVELOPMENT TO HIRING
• VISION
• PRINCIPLES
• TACTICS
• MEASUREMENT
• ITERATION

Outline

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• How to Position Your Business
• In terms of what comes first, product or positioning, Jackson suggests that the two should grow up side-by-side.

• How to Name Your Company

• There are three routes you can take when it comes to naming:

• How to Pull Together Branded Assets

• How to Prepare for Launch

Free Template Sales Agreement

[

YC_Form_SaaS_Agreement.doc66.0KB

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When Y Combinator startups make their first sales, we provide them with a sales template to make the legal part easy. In 2015, Y Combinator open sourced its sales template for the benefit of all startups.

The sales template here is specially tailored for software-as-a-service (SaaS) startups – i.e. companies who charge for cloud software on a subscription basis. You should consider YC’s template as a starting point and customize it to meet your needs. We’ve highlighted the areas that in our experience are most likely to vary startup to startup.

• Y Combinator Sales Template Agreement

Special thanks to James Riley at Goodwin Proctor for helping us draft the template sales agreement. Needless to say, YC & Goodwin Procter do not assume any responsibility for any consequence of using any of the documents linked here.

Getty

This article is the first in a series focused on Diversity and Inclusion in the workplace. Please note that references to minorities within the article are meant to refer to any underrepresented groups within an organization.

These days there’s an alphabet soup of terms focused on encouraging fairness in the workplace. Most organizations have a senior level executive of Equity, Engagement, Culture, Belonging, Fairness etc., but the most common phrase is “Diversity and Inclusion” (D&I) – which sounds great, but what does it really mean? Are these concepts similar, complementary, or different? The truth is that too many companies make the mistake of assuming that diversity and inclusion are synonymous or that one automatically implies the other…and that mistake is arguably a risky one. In fact, Gallup’s 2018 report “3 Requirements for a Diverse and Inclusive Culture” highlights the importance of acknowledging D&I as two very different concepts. The report concludes, “Gallup's research indicates recognizing that diversity and inclusion are very different things is the first step in the journey toward creating a uniquely diverse and inclusive culture.”

Defining Diversity

Indeed, diversity and inclusion sound pretty similar, but the truth is that they connote quite different concepts. The 2018 Gallup report defines diversity as “the full spectrum of human differences.” Dimensions of diversity might include visible traits like age, gender, disability and ethnic background or invisible traits like socio economic status, marital status and sexual orientation. Lori George Billingsley, Chief Diversity Officer for the Coca-Cola Company defines diversity as “the differences you can see or describe in people.” In essence, workplace diversity connotes just what we think it does – having a workplace that represents different types of people and backgrounds. Joni Davis, Vice President and Chief Diversity Officer for Duke Energy further explains, “We want our workplace to reflect the communities we serve.”

Duke Energy employees at the Charlotte Pride parade

Diversity vs. Inclusion

The 2018 Gallup report asserts, “Inclusion refers to a cultural and environmental feeling of belonging. It can be assessed as the extent to which employees are valued, respected, accepted and encouraged to fully participate in the organization.” Contrary to what some may assume, diversity doesn’t necessarily imply inclusion. In fact, the Harvard Business Review article “Diversity Doesn’t Stick Without Inclusion” focuses on this distinction. The article asserts, “Part of the problem is that ‘diversity’ and ‘inclusion’ are so often lumped together that they’re assumed to be the same thing. But that’s just not the case.” For example, while adding women to the board or promoting more people of color might enhance diversity, it doesn’t necessarily change the culture of the organization or ensure that these underrepresented groups will feel fully included and valued. Davis uses the analogy, “Diversity speaks to who is on the team, but inclusion focuses on who is really in the game.”

Society of Human Resource Management CEO Johnny C. Taylor, Jr. shares an interesting observation on the state of D&I initiatives in many organizations. “Honestly, most companies have reached increased levels of diversity. Inclusion is where most companies are focusing these days. In fact, some are swapping the D&I label for I&D to reflect their focus on inclusion.” His observations speak to the real difference between the two – and the inherent fallacy in assuming that one automatically implies the other. In fact, some would argue that the differences aren’t subtle and failing to understand those differences can be a grievous and potentially costly error.

The Dangers of Achieving Diversity Without Inclusion

Indeed, many organizations add a few women or people of color to a board or executive team and feel they’ve checked the box and can return to business as usual. That mentality is arguably naïve, misguided and truly dangerous because there are real risks associated with focusing primarily on diversity and largely ignoring inclusion. The aforementioned Harvard Business Review article concludes, “In the context of the workplace, diversity equals representation. Without inclusion, however, the crucial connections that attract diverse talent, encourage their participation, foster innovation, and lead to business growth won’t happen.”

Let’s explore some of the very real risks organizations face when they achieve diversity but not inclusion.

Inhibiting Psychological Safety

When Google conducted a study aimed at understanding what makes their teams effective, the results showed the number one factor for team success is psychological safety. Their report “The five keys to a successful Google team” asserts, “Who is on a team matters less than how the team members interact, structure their work, and view their contributions.” The study explains psychological safety with the question “Can we take risks on this team without feeling insecure or embarrassed? Organizations with high levels of psychological safety are generally regarded as those where team members feel free to speak up, ask questions, and make suggestions without fear of retribution or concern that their comments might damage their relationships or reputation. Inclusion seems to be an important if not necessary element for creating an environment of psychological safety. After all, can team members feel psychological safety without first feeling a sense of authentic belonging and inclusion? The latter seems to be a necessary ingredient for the former.

Creating a False Sense of Security

Since “non minorities” typically benefit from a default sense of inclusion, they’re often not aware that others may feel uncomfortable or excluded. As a result, when the composition of the organization changes to bring more diversity, it’s easy for leadership to fall into a false sense of security and assume the company has achieved major strides when the reality may be that they’ve only taken a first step.

Missing opportunities for enhanced business performance

It’s widely acknowledged that organizations pursue diversity and inclusion not just for ethical reasons, but also to realize enhanced business results and better financial performance. Arguably, the potential for enhanced innovation and business results is significantly handicapped without the realization of systemic inclusion. If there’s diversity in the organization, but those people don’t feel free to speak up, they’re not actively engaged decision makers or they don’t feel a true sense of belonging and therefore don’t passionately advocate on behalf of the organization, the boost to business performance will be limited at best.

Risking the Perception of Tokenism

The uncomfortable truth is that diversity without inclusion may be perceived as “tokenism” which can ignite a negative boomerang effect on the most well intentioned organizations. Indeed, those individuals from underrepresented communities placed in positions of senior leadership (or other areas previously lacking diversity) often feel like tokens once they realize that they may be “on the team,” but they’re not really “in the game.” What does that really mean? Possibly, they have a position of leadership but realize that they may still not wield the same influence as their majority counterparts. They may feel physically included but continue to feel like an outsider. They may realize that while there are members of underrepresented groups in leadership positions, the organizational culture has not shifted to embrace and fundamentally value those communities.

Organizations may invite underrepresented groups to participate on a board or leadership team and once those new invites realized they’re only tokens, they abruptly leave oftentimes with more disgust and frustration than they had previously. The organization is consequently worse off because they now have an even smaller pool of underrepresented minorities to approach to enhance their diversity profile, and they have a steeper hill to climb to strive to fully integrate these underrepresented groups into the fabric of the organizational culture.

In short, diversity in these cases may be seen as an attempt at a band aid or quick fix for systemic challenges that have not been fundamentally addressed. Lori George Billingsley shares that, “Inclusion is so much harder to achieve and measure because it’s more about a mindset.” Indeed, some organizations make the mistake of settling for checking the box of diversity without making the significant commitment to achieving true inclusion. They do so at their own peril as this short sighted approach can create enhanced levels of organizational tension, frustration and disappointment.

If diversity is a sprint, inclusion is a marathon. Each requires different training, conditioning and commitment.

Outline

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• Compensation at Startups
• Salary Bands
• Homebrew’s compensation philosophy

• Base salary and equity%20cash%20flow%20is%20not%20a%20stressor%20for%20employees%20and%202)%20equity%20is%20parsed%20out%20in%20thoughtfully%20so%20there%20is%20equity%20still%20available%20for%20future%20hires%20and%20refresher%20grants.)

• Balance cash and equity

• I’m a founder. Should I pay myself?

• I’m a founder. How can I possibly pay a new hire more than I make?

• Negotiation

• The Offer Process - Timing

• DOs

• DON’Ts

• The Offer Letter

Outline

• This is a short but great piece. Take a look for inspiration!

Outline

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• Reasons to Fire an Employee at a Startup: (not mutually exclusive)

• They are not getting done what they need to get done

• They are a bad culture fit,

• They are dishonest or unethical.

• Some Signs You May Need To Fire Someone

• The "But We Need To Get X Done First" Fallacy)
• How To Do It

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• Overview
• Benefits and drawbacks of remote work
• Mitigate remote work drawbacks
• Meetings
• Remote team communications
• Ensure accountability

• Managing remote employees

• Project Management Methodologies

• Further Reading

Kira Hudson Banks, Ph.D., is an Assistant Professor in the department of psychology at Saint Louis University, and a principal at consulting firm the Mouse and the Elephant. We spoke with her about why managers shouldn’t wait for a controversy to start talking about race.

Outline

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1. Make it easy for prospective remote employees to get started

2. Give additional calendar time judiciously

3. Screening applicants before spending your remote team’s time on low-quality candidates

4. Evaluate skills of remote workers through relevant, realistic experiences

5. Evaluate whether prospective employees fit into your culture

6. Give your team & potential new hires a hands-on experience with contract-to-hire

Many CEOs think the chief financial officer (CFO) is a utility position… and they’re dead wrong.

Outline

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• But when do startups need to build these functions and hire a CFO?
• When should we hire the ‘take the company public,’ experienced CFO?
• What should we look for?
• Can we wait to add the CFO?
• Why can’t I just outsource this function?
• How do we go about hiring a CFO then?

Outline

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• Brand exercises make big decisions easier
• Introducing the Brand Sprint
• Set the Stage
• 1. 20-Year Roadmap (15 minutes)
• 2. What, How, Why (30 minutes)
• 3. Top Three Values (30 minutes)
• 4. Top Three Audiences (30 minutes)
• 5. Personality Sliders (30 minutes)
• 6. Competitive Landscape (30 minutes)

Outline

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• Design

Outline

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• Step One: How to FIND a Coach
• Step Two: How to CHOOSE a Coach
• Ten sets of questions related to different aspects of coaching that you might find useful when talking to potential coaches

Outline

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• A CEO does only three things. Sets the overall vision and strategy of the company and communicates it to all stakeholders. Recruits, hires, and retains the very best talent for the company. Makes sure there is always enough cash in the bank. Read more!

Outline

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• Hire an experienced manager to run a team and watch how she does it.
• Trial and Error
• Get a formal or informal mentor
• Get an executive coach
• The biggest reasons CEOs don’t delegate

Outline

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• What KPIs are relevant?
• Why have we chosen these KPIs?

Outline

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• How does one prepare for a pivot, or rather, how does one create the proper conditions to pivot properly?
• To conclude…

Outline

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• Items for your calendar audit.
• 6am customer or partner meetings.
• Every press opportunity.
• Every event.
• Excessive networking.
• Unnecessary fundraising.

[

Carta Offer Letter Template (Word).docx4707.8KB

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Carta Offer Letter Template (Pages).pages4992.5KB

](https://s3.us-west-2.amazonaws.com/secure.notion-static.com/c22dd433-2e53-441d-9a50-a1b889cd2533/Carta_Offer_Letter_Template_%28Pages%29.pages?X-Amz-Algorithm=AWS4-HMAC-SHA256&X-Amz-Credential=AKIAT73L2G45O3KS52Y5%2F20210627%2Fus-west-2%2Fs3%2Faws4_request&X-Amz-Date=20210627T084202Z&X-Amz-Expires=86400&X-Amz-Signature=e1da21951eb58599193dc5a4d09496bf50b072fb7b844591732863657663c514&X-Amz-SignedHeaders=host)[

Carta Offer Letter Template (Pages).pdf4483.8KB

](https://s3.us-west-2.amazonaws.com/secure.notion-static.com/9de9fa1b-7e87-448f-97a2-234d1a6d69b3/Carta_Offer_Letter_Template_%28Pages%29.pdf?X-Amz-Algorithm=AWS4-HMAC-SHA256&X-Amz-Credential=AKIAT73L2G45O3KS52Y5%2F20210627%2Fus-west-2%2Fs3%2Faws4_request&X-Amz-Date=20210627T084202Z&X-Amz-Expires=86400&X-Amz-Signature=a618c2d6da32ea5fcaa62ef10d89cae8c8620fa97a13e8e89b5b2e71b8a94e31&X-Amz-SignedHeaders=host)

Outline

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• WHY DISCIPLINE — NOT VISION — GOES THE DISTANCE
• DISCIPLINED COMMUNICATION: THE THREE EMAILS EVERY FOUNDER SHOULD SEND
• IN SUMMARY

Outline

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• ANCHORING AROUND A METRIC: A LEADING INDICATOR FOR PRODUCT/MARKET FIT
• FROM BENCHMARK TO ENGINE: THE FOUR-STEP MANUAL FOR OPTIMIZING PRODUCT/MARKET FIT

1) Segment to find your supporters and paint a picture of your high-expectation customers.%20Segment%20to%20find%20your%20supporters,With%20your)

2) Analyze feedback to convert on-the-fence users into fanatics.%20Analyze%20feedback%20to%20convert%20on%2Dthe%2Dfence,However%2C)

3) Build your roadmap by doubling down on what users love and addressing what holds others back.%20Build%20your%20roadmap%20by%20doubling,Even)

4) Repeat the process and make the product/market fit score the most important metric.%20Repeat%20the%20process%20and%20make,As)

• BRACING FOR IMPACT

Outline

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• For Companies and Managers: Communicating option value to new hires
• For Companies and Managers: How we handle refresh grants
• For employees: Calculating the value of your stock options
• A final word on transparency
• Option value template for new hires/offer deck
• Option grant value calculator for candidates
• Option value calculator for current employees

Outline

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• The Wealthfront Equity Plan
• How It Works
• The Key: Consistent, Early Evergreen Grants
• What About Dilution?
• An Equity Plan that Works for Employers & Employees

Outline

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• Actually, start with the résumé
• Look at the portfolio design itself
• Look at each piece of work
• Generalize: What kind of designer is this?
• Making the decision: Should I interview this design candidate?
• What if they don’t have a portfolio?
• Some advice for designers

Outline

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• An Onboarding Plan: From Offer Letter to First Friday
• Offer Letter Signed
• Two Weeks Before Start Date
• The Friday Before The New Hire Arrives
• First Monday
• By The End of The First Week
• In-Between Time

Outline

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• 1. Schedule Everything
• 2. Use a Support System
• 3. Focus on Non-Work Time
• 4. Form New Habits
• The Bottom Line

Outline

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• Sleeping in Foreign Environments
• sleep and drugs
• dreams
• stages of sleep
• The horrible effects cause by a lack of sleep – Part 1
• light and sleep
• What should a person do if they have a hard time falling or staying asleep?
• sleep and evolution
• The horrible effects caused by a lack of sleep – Part 2
• naps
• The horrible effects cause by a lack of sleep – Part 3
• Sleep and Medicine

Photo courtesy wocintechchat.com

If you find this piece useful, find out more about how my firm can help your business. Visit vayaconsulting.com.

For the past two days, I have watched friends and acquaintances debate the merits of diversity in tech with ill-informed folks on social media. This stems from an ignorant set of remarks about Facebook’s inability to attract talent from backgrounds underrepresented in tech, essentially blaming it on “the pipeline issue,” one of the laziest analyses of this sector’s lack of diversity.

So, for the people who are working on this issue and are tired of repeatedly rehashing the defense, I have assembled an FAQ, to use the term loosely. These are some of the typical arguments lodged against diversity efforts, followed by responses. Copy and paste, refer people to it, use this information as a guide. Most of all, help improve it.

How can we diversify when the pipeline is so small?

The pipeline is wide compared to the yield. For example, each year in U.S. universities alone, 13–15% of computer science grads are Black and/or Latinx. If the tech sector is only between 3–5% Black and/or Latinx, we are losing significant numbers of people every year. Where are they going?

• Many are going to big companies with clearer career paths, not to the innovation economy where these things are often ill-defined.
• Some people are unwilling to come to or stay in the Bay Area, knowing the steady decline in the number of people of color we are able to retain in our neighborhoods. San Francisco in particular does not signal to Black candidates that this is a place for them.

People inclined to come into tech are dipping their toes in and deciding to leave before ever actually arriving. The anecdotal evidence is overwhelming that this is not a welcoming place. In the case of women of color in STEM fields overall, 100% report experiencing gender bias. If you were told that 100% of people like you face bias in a field, how inclined would you be to give it a shot?

In short, “the pipeline is too small” is the industry’s worn-out excuse for companies whose diversity efforts fail. The truth is we are here, we are tired of being invisible, and we are building pathways for more of us to get inside.

How can we hire the best if we’re lowering the bar by focusing on diversity?

Based on the “bar-lowering” logic of the questioner, tech companies currently — and miraculously — find all of the “best and brightest.” And yet, demographics in tech bear little resemblance to the makeup of the US, and even less resemblance to the Bay Area.

When we talk about seeking diversity, we are talking about hiring people who (a) meet the requirements of a job and (b) have not had access to tech jobs or are over-looked in current tech recruiting. There is no salient argument for loosening skill-based requirements in hiring. Being lax on qualifications does no one favors, especially the person being hired. What is more important to understand is the fact that hiring in most companies is a painfully inexact science, bolstered more by “culture fit” than any objective measure of skill-based excellence.

“Did you like the candidate?” a recruiter asks an engineering manager.

“His code was good, but I don’t think he is someone I’d like to grab a beer with. Pass.”

Are you hiring him to drink beer with you? Is that in the job description? If not, strike this analysis from the record. “Drinking beer” or any other similar non sequitur is a craven shortcut for “not like me.” So, on measures unrelated to the job at hand, people from underrepresented backgrounds are at a significant disadvantage in hiring.

(For the sake of research, I checked several large job boards in the U.S. for jobs with “drink beer” in the job description. I found one, at a brewing company.)

Equally important in measuring “excellence” is the fact that technical interviews are notoriously broken. This is perhaps one of the worst-kept secrets in tech. Technical interviews are lauded as great equalizers when in reality they are anything but: Steeped in bias, technical interviews reek of hazing and overwhelmingly favor those with dominant cultural context.

Google, the pioneer in ridiculous interview questions, recently lobbed this at an intern candidate:

Estimate the number of tennis balls that can fit into a plane.

This question assumes that

1. The candidate is familiar enough with a tennis ball that they can estimate its volume;
2. The candidate has been on a plane enough times that they can estimate volume; and
3. The job will require volume calculation on some regular basis.

If the candidate is missing knowledge about (1) or (2), they are already at a loss. “But who doesn’t know how big a tennis ball is? Who has never been on an airplane?” a hiring manager might ask. Answer: A hell of a lot of people. Does the candidate say “I’m sorry, I have never really held a tennis ball.” or “I have never been inside a plane?” For the dreaded fear of impostor syndrome, they definitely don’t.

So despite getting excellent math grades and being comfortable calculating volume, this candidate is stuck, based wholly on the cultural assumptions of the question. This has nothing to do with their mathematical prowess nor does it determine their ability to succeed in the position. Using this “methodology,” our industry discards so much talent at the doorstep of our biased hiring processes.

Those who say that they only want “the best” must examine their definition of “best.” Best at what, and as measured by whom? “Best” is a subjective description, as measured by a singular viewpoint steeped in a specific world view.

“Lowering the bar” is a red herring: Armed with no concrete definition of excellence and bias-laden interview processes, tech companies lay waste to the type of talent that could bring sorely-needed innovation.

Why can’t we get candidates from underrepresented backgrounds to apply for our job listings?

This is like saying “I wanted to invite you to dinner last night but I didn’t have your number. Sorry you missed a great party. Why didn’t you come?”

Every company must do the hard work to go out and find the talent, wherever it may be. A company that assumes everyone knows how to find them, their job listings, or that the brand “speaks for itself” is delusional. Through traditional methods like job boards and conferences targeting people from underrepresented backgrounds, to showing up at interesting and innovative events where diverse tech talent gathers, companies must do the legwork to demonstrate commitment and build a network.

Simply showing up is not a magic elixir, however. Each company’s reputation precedes it. People of color, white women, the LGBTQ community, folks with disabilities… our networks are strong. And if there is a well-earned reputation for what happens when our friends enter your company, all of the conference sponsorships in the world won’t fix that. In short, we know we’re invited to your dinner party, but your house is not somewhere we want to hang out.

I agree with you, but how do we make sure we’re doing it the right way?

The last time a white, male engineer with no expertise in diversity and inclusion asked me this, I asked to see some of his code. I told him I wanted to make sure he was doing it the right way.

“But you are not a developer,” he said.

Which is correct, and he is not an expert in diversity.

This is a thing that exists now. Diversity work hinges on best practices, research, and a ton of data. While not everything works perfectly (ever try to debug some code?), there is some real geekery behind effective diversity efforts. It is rife with nuance, grounded in years of experience and research, and requires massive amounts of iteration and innovation. And while many people have opinions about the best way to go about it, we need to level up on the general understanding of what this work entails.

So what is the right way? For that, I again suggest a technical parallel. Ask a developer a couple of questions, ones that an engineer colleague of mine calls “nerd grenades:”

“What language do you use to start a new project?”

“Given the choice, should my underlying physical page size be 4KB or 2MB? Which will ultimately be better for the performance and memory profile of my application?”

The answers vary wildly based on context, and may require substantial shared knowledge to fully explain.

It’s the same with diversity and inclusion work. No short answer in 140 characters or a single Medium piece is going to suffice. But those of us who have been doing this work for the better part of our careers know what to do. We have lived it, studied it, carved our professions from the best remedies for our communities’ pain. Now we need the resources, platform, and authority to do the best work of our lives and invest in the talent that will change this industry.

What even counts as diversity?

Here is a working definition I developed and still use. Please feel free to adopt it and help improve it:

Diversity means demographics that are underrepresented in tech and overly-predictive of career and educational success. This includes, but is not limited to race, ethnicity, gender, sexual orientation, age, disability and more.

Or to put it more plainly, all of the stuff about ourselves that we can’t control, but that have a massive impact on how we experience the world and how the world interacts with us. There is nothing about intellectual capacity or creative potential in this definition, because “intelligence and effort are evenly distributed, but investment and opportunity are not.”

The ubiquitous cop-out for many tech companies is their claim on “diversity of thought.” Yes, diversity of thought exists. Any time there are two people together, even if they are identical twins, there is diversity of thought. There is no legitimate argument to be made that all white men, for example, think the same way on any issue. However, as our demographic characteristics have an extraordinary impact on the shape of our lives including our overall life expectancy, expanding diversity across the axes listed above will likely yield a wider range of diversity of thought.

There are many other aspects of diversity that companies should value and desire. However, companies that find creative ways to avoid openly targeting race and gender diversity at a minimum are missing the mark. In so doing, they will miss the talent, too.

What is the benefit of diversity anyway?

At the risk of being overly-simplistic, there is one reason that compels most people who interrogate diversity efforts:

• Revenue. Greater diversity, specifically along gender and race lines, makes a company more money. I’m not sure there is more to say since we are, after all, discussing business.

It’s not the sole reason to do it, but if you really want to end an argument about whether or not diversity is worthwhile, this usually does the trick. Here are five other compelling reasons bolstered by data.

I hope this piece serves as a living resource for tech diversity and inclusion advocates. Please send me your thoughts and suggestions via pull request.

For too long, the industry that I love has gotten away with flimsy arguments cloaked in the myth of meritocracy. This has real consequences for a sector that desperately needs diverse talent. Those of us who have dedicated our careers to diversity in tech do so because we care deeply about building an industry where all people can thrive and feel supported. In so doing, we will help usher in the next set of technical innovations, built by people who experience the world in a myriad ways. From building inclusive dating apps to helping people access water, the next cycle of genius is ready to take its rightful place in tech.

Outline

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#1 Lower the barriers to communication

#2 Make shared objectives explicit

#3 Create a regular team cadence

#4 Make time to connect on a personal level

#5 Retrospect and build a knowledge base

#6 Meet offsite

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• This is the first part of a great passage on the role of the CEO by Elad Gil.

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• One question you should always ask yourself before a meeting is “Is it a Discussion or a Decision?”
• Process-Oriented Meeting
• Mission-Oriented Meeting

GitLab’s Remote Playbook comprehensively answers a simple question: “How do I work well remotely?”

Due to global issues concerning COVID-19 (Coronavirus), many teams face a new reality: They're remote, and they’re unsure when they’ll be able to return to the office.

For many leaders, the question of "How do we do this?" is a giant one. Whether it's unwinding from offices entirely and going all-remote, or attempting to level the playing field for in-office and remote team members in a hybrid-remote arrangement, leaders should consider key forcing functions to ensure a commitment to remote-first practices.

What you’ll learn in this eBook:

• Immediate tactics to build remote fluency
• Key steps every remote worker should take
• How to turn chaos into opportunity with long-term vision

Download the eBook now to stabilize your work-from-home team and dive deep on topics including asynchronous workflows, meetings, informal communication, and management.

Table of contents

• 04 Get ready for takeoff
• 06–07 Why equity matters
• 08–14 Key terminology
• 15–25 Building your equity strategy
• 26–29 Lessons from entrepreneurial test pilots
• 30–31 Communicating the equity package: What your employees need to know
• 32–40 Tax time: a basic guide for your employees

Available to read in your browser as well!

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• THE CASE FOR HITTING THE EMOTIONAL GYM:
• SELF AWARENESS
• EMPATHY
• WILLINGNESS TO PLAY
• CURIOSITY-,CURIOSITY,Dr.)
• MINDFULNESS
• RESILIENCE
• EFFECTIVE COMMUNICATION
• TYING IT ALL TOGETHER: THE EMOTIONALLY FIT COMPANY

This article is by psychotherapist, bestselling author, TED Speaker and podcast host Esther Perel.

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• CO-FOUNDER CONFLICTS: THE COVERT AND THE OVERT
• WHAT LIES BENEATH: A FRAMEWORK FOR DECONSTRUCTING THE COVERT
• IMPROVING OVERT CONFLICT MANAGEMENT: SIX PRACTICAL TIPS FOR CLEANING UP YOUR FIGHTS
• COMING TOGETHER TO MAKE A BUSINESS AND MAKE MEANING

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• What are OKRs?
• 1. Objectives must be Big and Motivating
• 2. KRs must be measurable
• 3. Use binary KRs sparingly
• 4. All Key Results must have dashboards
• 5. Key Results must be exhaustive
• 6. Pair Metrics with Counter-Metrics
• 7. Distinguish between Committed and Aspirational OKRs
• 8. Cascade OKRs up, down, and laterally
• 9. Personal OKRs are powerful. Use them to accelerate your career
• 10. Prefer a small number of tightly focused OKRs to a long list

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• SELF MASTERY
• 1. NOTICING
• 2. NEUTRALITY
• 3. PRIMING
• 4. SELF-COMPASSION
• 5. GENEROSITY
• 6. GRATITUDE
• ABUNDANCE AT SCALE

TABLE OF CONTENTS

What to do before you make your first hire 03

What to do on your employee’s first day 07

What to know about taxes, legal, and regulatory requirements 10

What to look for in your first hire 14

Additional resources 18

White Fragility:Why It’s So Hard For White People To Talk About Racism

2018, Beacon Press

White people in North America live in a social environment that protects and insulates them from race-based stress. This insulated environment of racial protection builds white expectations for racial comfort while at the same time lowering the ability to tolerate racial stress. Although white racial insulation is somewhat mediated by social class (with poor and working class urban whites being generally less racially insulated than suburban or rural whites), the larger social environment insulates and protects whites as a group through institutions, cultural representations, media, school textbooks, movies, advertising, and dominant discourses. Racial stress results from an interruption to what is racially familiar. In turn, whites are often at a loss for how to respond in constructive ways., as we have not had to build the cognitive or affective skills or develop the stamina that that would allow for constructive engagement across racial divides. leading to what I refer to as White Fragility. White Fragility is a state in which even a minimum amount of racial stress becomes intolerable, triggering a range of defensive moves. These moves include the outward display of emotions such as anger, fear, and guilt, and behaviors such as argumentation, silence, and leaving the stress-inducing situation. These behaviors, in turn, function to reinstate white racial equilibrium. This book explicates the dynamics of White Fragility and how we might build our capacity in the on-going work towards racial justice.

What Does It Mean To Be White?Developing White Racial Literacy

“Rarely will one find an analysis of whiteness (and the problems associated with it) that is as comprehensive as this one. From incisive and wide-ranging critiques of how white folks deflect, deny, and evade the topic of racism, and the implications of our own racial identity and position, to an absolutely on-point interrogation of how racism and whiteness influence white teachers-in-training, and thus, the larger educational process, Robin DiAngelo demonstrates the kind of clarity of thought so needed on this important subject.” —Tim Wise, Author of White Like Me: Reflections on Race from a Privileged Son

“With directness, sensitivity, and clarity, Robin DiAngelo leads the reader through a series of challenging and revelatory discussions that have profound implications for teaching and learning in today’s classrooms. Her question, What does it mean to be white?, underscores the pressing need for honest dialogue, particularly among white educators, about this tremendously important topic. I hope every teacher has the opportunity to read this book. Both they, and the students they teach, will be the better for it.” —Sonia Nieto, Professor Emerita, Language, Literacy, and Culture, University of Massachusetts

“This book goes well beyond Diversity Training 101. It is filled with comprehensive knowledge and useful tools for understanding racism and white people’s role in it. An invaluable resource for every educator, student, practitioner, and concerned citizen; you will be better prepared to address all forms of oppression after reading this book.” —Eddie Moore, Founder of The White Privilege Conference

DiAngelo, R. (2012). What does it mean to be White?: Developing White racial literacy. NY: Peter Lang. “What does it mean to be white in a society that proclaims race meaningless yet is deeply divided by race? In the face of pervasive racial inequality and segregation, most whites cannot answer that question. Robin DiAngelo argues that a number of factors make this question difficult for whites—miseducation about what racism is; ideologies such as individualism and colorblindness; defensiveness; and tendency to protect (rather than expand) our worldviews. These factors contribute to what she terms white racial illiteracy. Speaking as a white person to other white people, Dr. DiAngelo clearly and compellingly takes readers through an analysis of white socialization. She describes how race shapes the lives of white people, explains what makes racism so hard for whites to see, identifies common white racial patterns, and speaks back to popular white narratives that work to deny racism. Written as an accessible introduction to white identity from an anti-racist framework, What Does It Mean To Be White? is an invaluable resource for members of diversity and anti-racism programs and study groups and students of sociology, psychology, education, and other disciplines.”

Is Everyone Really Equal?An Introduction to Key Concepts in Critical Social Justice Education

2012 Critics Choice Book Award! from the American Educational Studies Association (AESA) for outstanding contribution to scholarship in the Social Foundations of Education field.

“This is a brilliant primer to help us consider what it means to think critically and to act for justice.” —Bill Bigelow, Rethinking Schools magazine

“The most accessible book on social justice I have ever read! The authors demonstrate that important concepts about social justice and political change can be both understandable and engaging.” —Mara Sapon-Shevin, Syracuse University

“Sensoy and DiAngelo’s book is to social justice what the Chicago Manual of Style is to the art of writing. It acts as a kind of guidebook. It introduces several basic fundamental ideas that form the structures beneath a number of essential concepts, thereby offering a clear road map for putting those concepts into action toward affecting change. —La’Ron Williams, Interfaith Council for Peace & Justice.

“This timely book offers a reader-friendly, unflinching approach to answering those questions on social justice that people are often afraid to ask. All critical educators need to get this text in the hands of their students.” —Darren E. Lund, University of Calgary

Sensoy, Ö. & DiAngelo, R. (2012). Is everyone really equal?: An introduction to key concepts in critical social justice education. NY: Teachers College Press. Written by invitation of James Banks for his _Multicultural Education_series with Teachers College Press, this practical handbook will introduce readers to social justice education, providing tools for developing “critical social justice literacy” and for taking action towards a more just society. Accessible to students from high school through graduate school, this book offers a collection of detailed and engaging explanations of key concepts in social justice education, including critical thinking, socialization, group identity, prejudice, discrimination, oppression, power, privilege, and White supremacy. Based on extensive experience in a range of settings in the United States and Canada, the authors address the most common stumbling blocks to understanding social justice. They provide recognizable examples, scenarios, and vignettes illustrating these concepts. This unique resource has many user-friendly features, including “definition boxes” for key terms, “stop boxes” to remind readers of previously explained ideas, “perspective check boxes” to draw attention to alternative standpoints, a glossary, and a chapter responding to the most common rebuttals encountered when leading discussions on concepts in critical social justice. There are discussion questions and extension activities at the end of each chapter, and an appendix designed to lend pedagogical support to those newer to teaching social justice education.

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• Recruiting Calculator
• Hiring Funnel
• Value of Referrals
• Close, Close, Close

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#1 Really Pick the Right Advisors for You

#2 Know When You Need Advising the Most

#3 Break the 80-20 Rule of Advising

#4 Give Your Advisors Permission to Help You

#5 Forge a Closer Relationship with Your Advisors Outside of Board Meetings

#6 Maximize Your Advisors' Super Powers

#7 Take Action When an Advising Relationship is Over

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• A DIFFERENT TACK FOR EXECUTIVE INTERVIEWS

1. Constrain your JD.

2. Split your interview process to separate skill assessment from fit.

• BRINGING IT ALL TOGETHER

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• Create Categories

• Light Touch Advisors

• Board Advisors (a.k.a. Senior Advisors, Lead Advisors — the title is up to you.)

• Maximize Potential Connections

• Redefine the Word "Chemistry"
• Next Steps
• Here’s what you should be looking for in meetings and correspondence:
• Making the Ask
• Keeping Relationships Strong