How to Build Company Culture That Makes Your Startup Team Want to Stay

A practical guide to building a high-trust, high-performing startup culture, from weekly rituals to quarterly offsites.

Why Most Startups Build a Business but Forget the Company Culture

During a particularly difficult time in my last business, we laid off nearly 80% of our staff. We reduced the team size in order to buy runway in support of a major change in how we were selling our product.

The business was already doing over $1M in ARR and supporting dozens of customers. We needed to keep those customers in order to keep the business alive. We also needed to engineer our way from a sales-driven acquisition model to a fully self-service one.

As leaders, we agreed if we were going to have any chance of making it all work we needed to retain our remaining team. If anyone left we were in trouble. And if there was an exodus we were doomed.

But these people had just been through hell. They had witnessed, or in some cases helped to plan and execute, the laying off of dozens of colleagues and close friends. Like many startups, our company was a close-knit team and for many employees their primary friend group.

In the days leading up to the layoff, I found myself obsessed with the question of employee retention. How could we get everyone to pull together, stick around, and see this through?

What Is Company Culture, Really?

I explored the question with my leadership team and cofounders, with trusted friends and advisors, with my coach, and even with my therapist. I do not remember exactly where the realization crystallized, but I remember that it did.

Somewhere in the years leading up to the layoffs, I had been exposed to the idea that a business and a company are not one and the same. We tend, in startup-land, to use the terms interchangeably. But they are not the same.

A business is a product or service sold to customers in exchange for money, attention, or some other form of payment.

A company is a collection of humans brought together around a shared effort or mission.

We speak a lot in startups about how to build a business: how to learn from customers, how to build a great product, how to test various acquisition strategies, how to raise capital, etc. But we rarely talk about how to build company culture.

Even when we do discuss culture, we treat it as an afterthought. A necessary complexity to be tacked on afterward once the business is working. Some mishmash of ping pong tables, free lunches, and paid vacation.

The realization that crystallized for me around the timing of that layoff was that I had for too long neglected the building of our company culture. While the business had some problems, and while we had a plan for testing our way through those problems, we would only have a chance of keeping the necessary humans together (and hopefully thriving!) if we tended to the company.

Learning how to build company culture while scaling the business became an obsession. Over the 24 months following the layoff, we were able to retain that entire team and also to turn our $1M, cash-burning startup into a profitable $5M+ business without adding any employees. The investments in the company paid off big time.

As we later began to add team members, they were invited into a thriving company, not simply a growing business.

The Cost of Ignoring Culture in Your Startup

Since selling that business and becoming a full-time CEO coach, I have witnessed a similar under-investment in dozens of companies.

Here is what I see over and over again:

• CEOs who feel fully out of touch with the experience their employees are actually having.
• Leaders who feel burned out and unable to do their best work.
• Teams of people who have worked together for years but barely know one another, and as a result, do not trust one another.

These companies are leaving a massive opportunity on the table: the opportunity to get the most out of their teams. Not through longer hours or stricter turn-around times on projects, but through building a place where people actually give a shit.

Business Focus vs. Company Culture Focus

The job of a CEO, and by extension the leadership team, is to:

• Hold the vision
• Recruit and retain the team needed to achieve that mission
• Resource that team with capital, clarity, and care

I have written elsewhere about some of the practices that support clear vision and team clarity and how to raise capital from venture capitalists. This post is largely about how to retain your team and how to build company culture that genuinely cares for its people. I will share some ideas on what is needed to create that culture and also some practical tactics to get you started. If you would like support beyond this post, please feel free to reach out.

How to Build Company Culture: Practical Steps That Work

To build a company culture and not simply a business, or put differently to care for the humans involved in the business and to enable them to pull together as a team and really thrive, we need to create space for different kinds of conversations than those which happen in the weekly operations meetings.

While team happy hours or fun offsite activities can be helpful in creating space for a team to get to know one another outside the day-to-day work, these activities are often helpful but insufficient in allowing a team to achieve real intimacy and alignment.

What a high-performing team actually needs:

• Space to explore and discuss the human side of the work
• Time for feedback on how the team works together
• Regular discussion about whether you are living your values
• Alignment between the company you are building and the lives your people want to live

Let me share some of my favorite tactics, variations of which I have seen work in my own companies and in those of many clients.

Create Shared Language Around Culture

A helpful starting place is to separate out in your own mind and in internal communications, the concept of the business and the company. You might introduce the differentiation to your leadership team, your board, and your employees in order to establish a shared vocabulary going forward.

As you do so, you create the opportunity for distinct discussions and experimentation on what is needed for the business vs. what is needed for the company culture.

Run a Weekly Company Check-In (Not Just an Ops Meeting)

One of the most powerful things you can do for startup employee engagement is to separate your operational meetings from your culture meetings.

You likely already have some kind of weekly operations meeting aimed at things like checking in on key metrics, reviewing work accomplished, eliminating blockers, etc. But if you are like most teams I meet, you likely do not have any weekly time aimed at connecting and supporting the humans involved.

Set up a dedicated company check-in once per week. I am a fan of end-of-day Thursday. Here is a sample agenda:

A Sample Weekly Culture Meeting Agenda

1. Check-in

Sit in a circle if possible, or on video. For larger teams, split into rotating smaller groups for cross-pollination. I am a fan of a simple red, yellow, green check-in.

The goal is to hear how everyone is arriving. As trust grows, people share more. If someone checks in yellow or red, the team can ask "how can we support you?" This creates a practical way to build trust and team building in your startup.

2. Gratitude

Ask each person to share one thing they are grateful for at work and one outside of work. This builds intimacy and resilience. Startups are fucking hard. Sharing gratitude helps bolster a team.

3. Values shout-outs

A time for anyone to acknowledge a teammate who lived your values this week. This keeps values active, not just words on the wall. It can also surface concerns about where the team is falling short.

4. How can we work better as a team next week?

This is my favorite part. Ask the question, then leave space. Allow for silence. Over a few weeks, this becomes the place where anyone can bring concerns or conflicts into the group. It also reduces the "drive-by complaints" that eat up a leader's week. Invite people to raise broad team concerns here, and handle one-on-one issues directly. It is not easy to build this openness, but the impact on your calendar and culture can be profound.

5. Any other open questions about anything?

A catch-all. Invite people to ask anything of you or the leadership team. This ensures nothing gets buried.

6. Closing: What are you most looking forward to next week?

Go around the circle and share the one thing you are most looking forward to next week, at work or at home. This gives the meeting a positive, connecting close.

There is no right way to do any of this. Experiment and make it your own.

What Should a Company-Focused Offsite Look Like?

If your team has a practice of company offsites, it may be helpful to divide the time in two with half focused on business building and half on company building. I love to do quarterly, two-day offsites where the first day is focused on the business and the second day is focused on the company culture.

For the culture-focused day, try longer-form versions of the weekly meeting elements above, plus these exercises:

1. The 10-Year Question

Give the team an hour to discuss: What would it take for you to be excited to spend the next 10 years on this mission with this team?

This question provides a way for the leaders, and everyone else, to learn about the kinds of changes that would support deeper alignment between the work people are doing and the lives they are living. You obviously cannot implement every idea, but you might find some real treasures that have a profound impact on preventing burnout and helping your people do their best work.

2. Check-in on working norms

How well is the way we are working together supporting us doing great work? Where are things like Slack interruptions, too many meetings, or other unhelpful work practices getting in the way?

Poorly run companies never talk about their working norms. Well-run companies make their working norms explicit and invite revision and evolution.

3. Partner walks

Invite team members to break into partners with someone they do not know super well. Give a prompt like: What would you most love to experience in your life or work this year? Set a timer for 20 minutes, 10 minutes out and 10 minutes back, with a different partner sharing each direction. When back, each person shares what they learned. Use this to find ways to evolve how you work together.

4. Origin stories

A powerful way to help a new team bond. Take turns sharing:

• Your full name
• Your parents' full names
• Your place of birth
• Your place in the birth order
• One challenge you overcame in childhood

It may sound simple, but it has a powerful effect. We immediately feel closer. And the last question reveals why each of us is the way we are.

These are just a few ideas. Feel free to brainstorm your own and invite your team to contribute. If you would like help with design or facilitation, let us know.

The Return on Investing in Your Company Culture

The return on investing in your company culture, and not only your business, is profound. If all of this sounds new and messy, that is totally ok.

There is no perfect in any part of startup building, and there is no perfect here. It is ok if your early efforts feel a bit disorganized or uncomfortable. Every step toward building a strong company culture will pay dividends.

If I can support you in any way as you explore how to build a place where you and your people can thrive, please reach out.

In the meantime, wishing you connection and ease. I know the days can be long and the road difficult.

-Matt

Frequently Asked Questions

How long does it take to build a strong company culture?

There is no fixed timeline. Most teams begin to feel a shift within 4 to 8 weeks of consistent practice with weekly check-ins and intentional culture conversations. The key is consistency, not perfection. Start with one new ritual and build from there.

Can you build company culture with a remote or hybrid team?

Yes. Every tactic in this article works on video. The weekly check-in, gratitude rounds, and open questions all translate well to remote settings. The important thing is creating structured space for human connection, not being in the same room.

What is the difference between company culture and company values?

Values are the words you put on the wall. Culture is how people actually behave when no one is watching. Building culture means creating rituals and feedback loops that keep your values alive in day-to-day work, not just in onboarding decks.

How do I know if my startup's culture needs work?

Common signs include high turnover, frequent "drive-by" complaints to leadership, a team that avoids difficult conversations, and a feeling of disconnection between leadership and employees. If people are leaving or disengaged, your culture is telling you something.