Teambuilding Playbook

Lessons and personal reminders from over fifteen years managing people and teams in new and fragile organizations.

These are my notes for creating a company employees love. Lessons and personal reminders from over fifteen years managing people and teams in new and fragile organizations.

It is hard. I’ve created this to a) clarify and record my own thinking; and b) share it with people who may be interested in working with me.

If anything here resonates with you, please take it. A caveat: company culture must be authentic to the founder. You should take what you connect with, modify whatever needs changing, and discard everything else. Make it your own.

Contents

Why this matters
Three Principles for Teambuilding
My Teambuilding Philosophy
Intentional Leadership - Big Boulders
Intentional Leadership - Useful Tips
How to Have a Successful All Hands
Closing a Candidate
Successful Onboarding of a New Hire
Have the Hard Conversations
Employee Pulse Survey
How to handle a key departure
Topics to Come

Why this Matters

As a startup, your team is your most valuable asset. You need to attract and retain talent to get anything done.
Earning the right to work alongside gifted colleagues is the first force multiplier needed to accomplish great things.
Talented employees have choice, and look for work that is purposeful.
Inspire a team with personal connection to the story of the organization.

Three Principles

Return to this section when you are lost. Always re-center efforts on these three principles:

Care about individuals. Not ‘show you care’ or pretend to care - actually, genuinely make your team a priority.

Practical Tip: Audit your calendar every two weeks - simple calculation - how many minutes did you invest in the last two weeks on team health? Target ~20-25% of your time - less and you are risking neglect, more and you may be putting out too many fires or serving as an unnecessary crutch for someone/something the team is missing.

Diversity Matters. Everyone comes from a different background and perspective. Make sure you are building - from the very start - an organization that brings a range of perspectives to challenging issues. This is not just demographic diversity, it is also philosophical and temperamental (introversion, extroversion, etc). Remember especially ‘hidden’ dimensions like socio-economic diversity. Audit quarterly at least - how are you doing?
Get Data. You need to know how people are feeling so you can support the team. Most important here is data over time (longitudinal data), so you can see how it evolves and when you need to step up support for team morale. Make consistency a priority.

Practical Tip: Use Employee NPS Survey (below) constantly. A regular cadence will provide valuable lessons over time. Other key metrics - regretful turnover (any patterns?), founder confidence ratings, survey participation rate.

Team Building Philosophy

Keep it simple. Develop a working theory of successful teams. Return to it whenever you have lost direction. Keeping this as a mantra creates consistency for you and the team. Make it your north star for every and all team conversations.

‘People want to be a valued member of a winning team, with colleagues they respect on an important mission.' (adapted from Joel Peterson's work)
‘Valued member’ - show the person why their work matters to the company. Make it ladder up to the overall mission - take time to walk through the steps that show how good performance in the role will impact the company. For direct reports, do this in 1-1s, and follow with an email to them so they see it in writing. Repeat this in casual conversations around the office. In interviews with new candidates. The ladder from role to mission may be clear to you, but it isn’t to them.
‘Winning team’ - show the person/team how you are making progress as a team. Remember you can define ‘winning’ how you like as long as it is truthful and meaningful to the person/team. And it can change. Every company has ups and downs. Some months winning can be revenue growth or a star new customer, sometimes it can be a new feature/product shipped, sometimes it can be just a piece of feedback from employees/customers. You are always winning at something. Your job is to provide visibility to these success stories across the company. Make sure they are shared and appreciated.
‘Colleagues they respect’ - People want to feel like they are learning, and the easiest way to do that is from colleagues. Note this point is not people they ‘like’. - affinity can be a foundation for respect, but that won’t drive retention and success, particularly for high performers. Get data on how team feels about colleagues (survey below, but also in conversation). When there is a weak person/team/department, you need to solve the problem - either move the person to put in a position where respect is gained, or separate.
‘Important mission’ - You need to inspire people with more than revenue/profits alone. How is the world a better place if the company is successful? Find new ways to tell this story so it doesn’t get stagnant. Repeat, repeat, repeat.

Practical Tip - ask other team members to speak to the important mission. They will use different words, providing new opportunities for connection, and can be even more powerful mission ambassadors as the team grows.

Intentional Leadership - Big Boulder

Know the Why. Why is this person here? What are they looking for in this experience? How does this role intersect with their goals in life? Simply asking this question, and recording the answer, improves the chances of a great relationship. First, it shows you care. And second, it affords a roadmap for fulfilling that persons why.

Reminder: I tend to project my own goals - making the (incorrect) assumption they are like me, and motivated by similar goals (purpose, money, status, etc). Just ask. Don’t judge someone else’s why. Try to understand it.

Intentional Leadership - Useful Tips

Keep Active Notes - Create a living Google doc with your HR notes.

First Tab - Personal Connections. Write the names of spouses, children, dogs, favorite teams/hobbies - ways you connect with key people. Doesn’t have to be everyone, but should be all your direct reports and a handful of others in the org that you have visibility.

Get the information in 1-1s or other conversations (quick note in your notes if you are taking notes - and you should be in 1-1s).
Look at the sheet before your 1-1, and reference the name of the person in a direct question. Get to know your colleague and their life.

Second Tab - Significant 7. Imagine each individual walked into the office and quit. Actually picture it. Who are the 7 people that it would be most painful to lose? Write their names down in a new tab (Called ‘Significant 7’).

Next to each name, write your thesis for what motivates them. Why are they here today? What do they want out of this experience? Given their importance to the organization, your job is to make sure the organization is delivering this to them.
Revisit this list monthly - update people and hypothesis

Do Skip Levels. Open up channel of communication to people who report into the people that report to you. Can be monthly small group lunch with less than 5 people that don’t report to you, followed by walk or 1/month more focused meeting with a direct report of your direct report. The lunches build trust (and help that team get alignment with mission/vision/strategy), the meeting offers chance for specific feedback on your direct report, the company overall, areas you are missing

How to have a successful All Hands

First question to ask (for all meetings): Why do you have an all hands now? What purpose does this format have that no other meeting could accomplish? This answer may change over time - revisit the question every 60 days (short calendar reminder on your calendar to prompt)

Early on. (less than ~15 employees, not yet validated by investors or customers). The reasons for all-Hands are:

50% - confidence in your leadership and the company
30% - building team spirit / connectedness
20% - learning / surfacing opportunities / issues

The percentages may vary over time, even within this stage. Consider each week what should be the goal, then plan agenda around it. Confidence in the company/leadership does not mean you are talking each week - the opposite may be true. Bringing in third-party validator of the idea (frustrated customer, market leader who sees opportunity, etc) can hit same goal more effectively.

Later (more than 20 people, clear market validation):

90% - alignment in common purpose
10% - inspiration and shared

Choosing Topics: What topic is relevant for everyone? Aim for 90%+ 'fit' for the topic - 9 out of 10 should be interested, especially early on.

Product update - something that is shipping that week, or roadmap update
Rotate team updates - but not from senior most people on the team. Let all levels of team present updates, what they are learning and how that is shaping their work/strategy.
Light hearted game with new colleagues - two truths and a lie that the new person leads (Important: give them a warning before. You don’t want people to be surprised). Trivia on skills, something else to humanize team to each other
Bring in a Board member, investor, industry contact, customer. Talk about industry and bring toward the mission/strategy of the company.
Regular Q&A - google form to get questions in advance, but also leave time for live.
At least every 6 weeks have the CEO or Co-Founder revisit long term vision / critical questions in front of the company. These should be no more than 15mins presenting - likely reiterating -- then open Q&A. Standing in front of the entire company and opening to questions is a powerful symbol of transparency.
There will be awkward silences. That is ok. Let them sit. It is the repetition of the meeting that matters. Cadence and predictability

Closing a Candidate

On your choice: Focus on hearts and minds as your selection criteria - do they have skills to do the job (or direct path to get them) and does this role make sense as a part of a career journey they are undergoing. Why? Ask them directly. Select talent and mission alignment over experience every time.
On their choice: Always counter-sell for a senior hire. Make sure they know all the challenges and uncertainties. Be upfront before they sign, to avoid any surprises after.

Successful Onboarding of a New Hire

The work starts the moment they sign. Everyone that interviewed them sends an email with a specific point about why they are excited about that person joining. Should be relevant to experience talking with them, regardless of how they voted in process.
Follow up with key touchpoints before they start (computer, onboarding doc, press or industry article)
If long gap, hiring manager put a calendar reminder at least every week for a short note - something happening in the company, an opportunity or press clipping - goal is to keep in touch
Onboarding document in their inbox by 8am on start date (not before)
Thoughtful explanation of organization, how the role fits, why you are excited about their specific impact to the company goals
30/60/90 day expectations
Key personnel they need to learn from - names and what to discuss
Do a six week check in - great opportunity to learn from employee. What is as expected? What is different about the company than you expected?

Have the Hard Conversations

Remember, you do an injustice to your colleagues when you don’t have hard, honest conversations with them. People and teams grow through interpersonal dynamics. Avoiding that gift to your team is not who you want to be as a leader. Don’t assume you are right in a conflict, but don’t shirk the responsibility you have as a leader to initiate the dialogue.

Practical Tip: Short email to yourself after each ‘hard’ conversation. How could you have done it better? Count the number of emails. If you have less 5 / month, are you avoiding your responsibility?
Prepare. Think ahead what you want from this interaction.
Don't cross the net. Don't assume intent - make point about impact on you and others in direct, neutral language. Listen. Listen to understand and find a path forward that meets the person's why? and the organization goals.

Employee Pulse Survey

Perhaps the most important tool for long term teambuilding. Keep short - here is the template.

Need to do every 90 days - want trendline and trust from the team.
Read-out to the team within two weeks of completion of survey. As much transparency as possible, without harming any individual

Managing a separation of an important employee

Managing a separation process is never easy.

Focus on just two goals: Clarity and dignity

Clarity. Your job is to prepare thoughtfully to provide as high a probability of clarity as possible in the initial meeting. Some points of clarity that are needed:

Why is this happening?
When is the last day?
What severance is being offered?
What will messaging be?
Will anyone be open to references in the future?

Dignity. Simple rule - manage the situation such that if roles were reversed you would find actions of the organization worthy of respect. That means you bias away from sharing information with anyone that doesn't need to absolutely know. There is tremendous pressure to talk to the team about the departure (if an Exec), stay true to the goal of dignity.

When talking in private or public about the situation, you should be comfortable with all answers you provide if the person were sitting right next to you. Here’s the formula (this is for a very prominent company departure, not every leadership change):

Email team immediately sharing the departure and saying it will be discussed at next All Hands (another benefit of regular all hands)
At mtg, open with a broad, true statement that is positive to the person. “As you know, XX left our company this week. She has made significant contributions to our company over the past YY years. I know she is well liked and well respected by many of you.”
Make a personal, positive, and true statement. “I’m saddened by this. I will miss her many gifts in helping me think through YY. She was also very valuable in building ZZ work, a project that is important to us going forward.”
Acknowledge dynamic, but repeat policy. “When something like this happens, it is natural to want to know more. We don’t share more as a policy. We have this policy because it is how I would want any organization I leave to treat me if I were departing. There are many reasons people leave our company, and it isn’t our story to tell you why this happened."
Make it personal to the audience. One of the benefits of working here is we hire exceptional people. That creates an environment of learning and growth for us all, but it also makes departures like this harder. My recommendation to you: spend time with the question of what is behind your curiosity to know more? Or, are you worried XXX’s departure is a signal about the company overall? Or about what is going to happen with the product/finance/XX team? Or perhaps something else? Explore these feelings, and bring them to your manager, or me if you like. Talking it through can help us focus on what matters most as we continue to build in the days ahead.
Get data. If you are open to it, I’d like to hear more about what comes up when thinking about this. We won’t talk through XX specifically, but I can speak to other related questions that may be sparked in your mind with this transition. We will send a short anonymous survey after this meeting, and dedicate some time next All Hands to talking through the questions and responses.
Stay consistent in all 1-1s too. You need to follow your own policy. Don’t say it publicly to the team, then contradict yourself with a key report.

Topics to Come / Still in development

Turmoil is normal. It isn’t easy. It will always be a roller coaster. You aren’t the worst company to work at, nor the best.
Don’t expect 100%. All employees will not skip to work every day. That isn’t the expectation. You are tilting the scales in favor of more people on more days being marginally happier at work. That is success. Don’t beat yourself up when you can’t win them all.
Trust Equation. Reliability x Credibility x Authenticity / Self- Interest. Where to focus my time - how to diagnose with other people.
Setting a Company Purpose. If you are just starting, start here. No more important subsequent decision than why your company exists. Think deeply about. Write it down.
What problem you plan to solve; how you'll solve it; Why it's important
This is foundation for so many future decisions. Most importantly, it provides the reason why employees want to work for you, and investors want to invest in you.
Setting a Personal Purpose in the endeavor. Always remember and push for detailed answers to @ThisIsSethsBlog's advice for founders:
What are you willing to invest (time, reputation, emotional bandwidth, $$)?
Who do you want your customer to be (you will fail if you don’t have empathy for customer)?
What experience do you want (pay dues for big $$, balance, joy)?
Financing Your Company. Full Blog Post here
Raising outside equity commits you to a defined path for success. You are obligating yourself to growth and change. Every month, quarter and year needs to show significant growth, or it is judged as a failure.
Is that your goal with this organization? Do you want it to be huge? Is the business well suited to constant growth cycle?
Remember, it is exceptionally hard to get off the equity path once on. There are a few options at the start, consider:
Structure a company led buyout. Ask investors what success looks like for them, then allow for company led buyback if that return is achieved. For example, put in 10x (or more) clause that company can buyout position in next 10 years at 10x capital paid
How to do an important reference check: First step, whether direct or backdoor reference, make the person you are talking to knows you care about getting this right. Before the call, you should know who they are and their relationship to candidate first (2min linkedin search)
Connect with the person first - common geo, interest, school, anything to show you know them and background, have common connection. That helps build trust and reduces chance they want to bs you
Confirm relationship b/w contact and candidate.
Say what has impressed you about the candidate so far - “Sally has impressed our team. She seems great at XX and YY, with a lot of experience that would be relevant for us.’
Describe the role and where you are as a company. The person you are talking to knows the candidate better than you, but you know the context for the role better than them. Your job is to bridge that gap so they can give valuable information.
Assume the person you are potentially hiring is talented. What you are trying to do in this call is determine if their skills and talent fit well with the role you have open at the moment.
What can I do to coach this person to get the job?
How can I help this person best succeed (probe 2-3 times here, need to draw out response)