How To Avoid Bad Startup Culture

If you are not paying attention to your startup culture, I have news for you: you are already building a culture into your company. Chances are that is not the culture you want.

Every company has a culture. It is a summation of all the habits and practices that make up the work. It is every choice, good or bad, made by every person involved. Every action sets a precedent, a “how we do things here.”

This is how we are wired. We are naturally social beings and are strongly predisposed to fit in to the group we find ourselves in, and to emulate their behaviour. This reinforces culture further, and compounds when more people are involved.

A culture grows like plants in a garden. You cannot stop the life from growing, but you can decide how and where it grows. Left unattended, weeds will grow alongside the flowers. The key is recognising this and putting in the work to shape it.

Here is a quick primer on how to do the minimum to avoid bad culture, and how to get good culture going with a little attention every so often.

How to get good culture started

You need to be intentional with your culture, but you also need a successful business. Paying too much attention too early is wasteful.

Many years ago in my first startup I learned this the hard way. I sat with my team for several days trying to think through what kind of company we wanted to become. Unfortunately, I paid too much attention to the culture and not enough to our sales funnel. We ran out of money before we could become that company.

Culture, like a garden, is best attended to little and often. If you are still a small team, do the minimum now to set things up and return to it regularly. At Cherrypick we met for an hour every week with our early team, purely to discuss our company culture. It was a great way to keep the culture alive and evolving intentionally.

Figure out your values

You might cringe when you hear about an organisation mission or its values. So often companies come up with meaningless lists of values that rot on the wall and reek of insincerity and hypocrisy. We all know of companies that preach one thing and do the opposite.

However, without any idea of what you stand for, you will not be able to shape the company into what you want it to be. Without a clear idea of how you do business, and what is important to you, the weeds of bad culture will grow.

At Cherrypick we have a set of core values that we have agreed on, which we called operating principles. They have defined how we interact as a team, how we pay people, and how we decide what to work on. They have helped us keep the speed of innovation high over the years, and continually keep us focused on what is important.

How to create a set of values that are not laughable fallacies but can shape you and your team behaviour? It comes down to how you go about it:

• Involve everyone in their discovery
• Beware of hippos
• Boring culture is ok
• Organise your values into types
• Road test and tweak them

Involve everyone: start with your co-founders and early team

The values conversation should begin with the co-founders and the early team. Who to involve will depend on your honest appraisal of the current situation.

If you are working on your own, write down the values that are important to you, and review them regularly. Make sure you are clear about them before your first hire or when choosing a co-founder. Be prepared to evolve these ideas as you build your team, but it is useful to discover your core values early, as these are not likely to change (see below for more on core values).

If you have a small team with no indirect reports, and you are broadly happy with the team culture at present, involve everyone in the company in the full process. It is really important everyone is involved as much as possible or the decisions you make will not stick.

If you are happy with your co-founder relationship, but unsure about some of the cultural behaviours in your team, then spend time discussing the values with your co-founders first to make sure you agree on what is important. You can then run a wider workshop with the rest of the team. Warning: if the culture in your team is not what you want, and you uncover fundamental incompatibilities that cannot be resolved, then you will need to be prepared for some of your team members to leave. This is good. Better now than later when the culture is set.

If you are unsure about the culture being set by your co-founder, then drop everything and work on that relationship first. It is the most important thing you can do right now. Come back when you agree about the culture you want to set. If you cannot agree, you are best to part ways now.

If you already have a larger team, start with the handful of people who report to you directly. Once you are sure about the culture you can run bigger workshops with the rest of the team. This journey will take longer, and uncover more issues.

Beware of hippos: come up with individual lists of values

Given your starting set of people, come up with a list of values that you see on display within your team, and that you might want to see, or might not want to see. Ask the team to work for a while on their own list, then bring them together for discussion, combining and removing duplicates.

It is important that people create lists on their own at first to prevent groupthink and ensure proper divergence of ideas. If you do not do this, you are likely to converge on the “highest paid person’s opinion” (HiPPO), which is likely to be you if you are the founder.

While HiPPO-driven decisions can be difficult for you to spot, they are obvious to your team. When it happens, you will notice your team gradually disengaging from the process. For them, it feels deeply disempowering - they will see that their input is not truly valued and stop investing in the process. This defeats the whole purpose of involving your team. Values imposed from above will not lead to meaningful behavior change.

Use boring culture as a starting point

One way to come up with a list of values is to think about people in your organization or elsewhere that you admire, and think carefully about how they go about their work. Write down the driving principles that you think are important to them and that guide them, even if they would not be able to articulate them themselves. You do not need to be original. Boring culture borrowed from other companies is a good starting point: Charity Majors writes eloquently about this topic.

If still unsure, Andrew McAfee’s The Geek Way provides an excellent framework of values that have proven successful at many of the world’s leading tech companies. The book examines how top tech organizations operate and identifies their common cultural traits, which he distills into four core values. They are worth including on any startup list for discussion.

Scientific approach: Decisions should be driven by data and evidence, not authority or tradition. Teams should regularly run experiments and measure outcomes to validate their hypotheses. Most importantly, they must be willing to change direction when the data contradicts their assumptions.

Speed of execution: Great teams optimize for rapid learning through quick iterations and small batch sizes. They focus on getting working solutions in front of customers quickly, even if imperfect. They understand that speed of learning is more important than perfection on the first try.

Openness: Information should flow freely within the organization, with transparency being the default state. Teams should share context broadly and create environments where ideas can be challenged constructively. This openness extends to mistakes and failures, which are treated as valuable learning opportunities rather than sources of blame.

Ownership: Teams should have both the authority and responsibility for their outcomes, not just completing assigned tasks. They should be able to make decisions about their work, especially if they are reversible, which most decisions are. Conversely, they should be held accountable for results. This ownership mindset means caring deeply about the long-term success of initiatives, not just short-term deliverables.

Organise your values into different types

Once you have come up with your lists, compare notes together and combine anything the group agrees is similar (be careful of HiPPOs again). You should now have a big list of perhaps 10-20 good ideas.

This is the crucial part. To create a set of values that are actually useful and believable, organise them into these four distinct categories, so they can be both believable and aspirational, and not just nice ideas on a wall.

Patrick Lencioni’s The Advantage provides an excellent framework for organizing values into types.

Core Values

These are the fundamental values that define your organisation at its core. They are the principles you would “bleed for” - the non-negotiable aspects of your culture that you’ll defend at all costs. They are not things you wish to be or want to have, they are already a natural part of who you are at a deep level.

You should try not to have more than a very few core values. If you have more, then it will not be clear which are the most important things to you, and it will be hard to sustain them.

When faced with criticism or challenges about these values, you’ll stand firm because they represent a core part of your identity. They cannot be compromised, and you will defend them at all costs. Every major decision, from hiring to strategy, should be filtered through these values - they often reflect the fundamental values of the founders. People who cannot embody these values or who do not agree with them will not last at the company - it is best to know that as early as possible!

A couple of examples:

“Just get it done” on the surface sounds like a good value. Is it a core value for you? If so, then people will move mountains to get things over the line, even if it means breaking a few rules, or working late. Is that true for your company? If so then you will appeal to potential hires who are happy with this level of commitment. If they are not then you will not be able to hire them, and that is a good thing as they will do much better elsewhere. You will also have to celebrate and tolerate rule breaking in your team for the right reasons. How far can people push the boundaries? If it is a core value, then you will need to be comfortable with people defying you and others’ feedback to get something finished. Are you comfortable with that?

A core part of the Cherrypick value “move fast” is “working in plain sight”. We broadcast all our work and keep everything open and public as much as possible. We do this in a public Slack channel, giving regular updates on progress, and we publish a summary of all our results clearly so they are easy for others to understand and digest.

This means that our Slack channels are all public, and full of activity. This can be a disadvantage, so we have to organise them carefully and post in the right places to ensure people are not overwhelmed with noise. We also give and accept feedback on our work at any point, which can be uncomfortable if you are not used to it. We do not do big reveals but publish partial work regularly for feedback.

This value is important to us. It helps us move fast as mistakes are found and fixed quickly, and work is optimised as it is being done. It does not suit everyone. A number of early employees prefered to work more privately, not show their methods, and do larger presentations to the rest of the company when things were “finished”. Some did not get used to the level of transparency we expect. They left the company, and are much happier elsewhere. If something is a core value, you will be ok with that.

Permission to Play Values

Teams often get stuck debating whether fundamental traits like “integrity” should be included in our values list. I have spent many a pointless meeting in the past discussing whether integrity should be a value. The answer is (usually) “yes, but as a permission to play value”.

These types of values are the basic expectations that should be present in any professional environment. While they are necessary, they do not distinguish your culture from others. Examples of values like this are “teamwork”, “respect” and “integrity”. They are not core unless we are prepared to adopt very high standards on these values that distinguish you from other companies, and they are already an extremely important part of who you are.

Aspirational Values

These values represent where you want to take your company. They’re the cultural traits you recognize as important but haven’t fully developed yet. They acknowledge that culture is a journey, not a destination, and show your commitment to growth.

This is a great place to take people forward without being too prescriptive. If you say “respect” is a core value but people are not showing respect towards each other yet, your values will not be believable and people will fail to take them seriously. However, if you say “respect” is aspirational you are showing leadership. You are setting a direction to grow towards and challenging your team to move in that direction together. “Will we respect each other more?” is a question not a command, and more likely to be adopted by the team.

You do not need people to be embodying these values yet, but you should be working towards them. New hires ideally should already be embodying these values so that you as an organisation can learn from them and grow towards them.

Accidental Values

These arise spontaneously from within the team without the leader’s involvement. They are not intentional, but they are real. They can be good for a company, but can also be bad for it. You need to keep a careful eye on them as they arise.

An example: it is likely that as you hire your team it will become more homogenous over time without realising it. People naturally know and hire people who are like themselves. “We hire people like us” is very unlikely to make it onto a company values statement, but it is still shaping your culture unless you actively work on avoiding it. An aspirational value such as “we ensure diversity of thought” could be a way to avoid this.

Road test your values

Once you have your list, whittle it down to the core set and road test them for a while. The work you have done so far is pointless unless they are used. Keep it low key and treat them as a test, which will help with buy-in. Once you have used them for a bit, revisit them as a team to see if they are still working and decide if you need to tweak them. Keep the conversation going.

Here are some ways to road test your values:

Call yourself out when you do not live them

If you discover an example of where you are not living out the agreed values, call it out. Apologise to the team, promise to do better, and ask them to hold you to account. Do this as publicly as possible, especially if a core value is at stake.

Celebrate success

We have a “celebrations” channel in Slack where we post examples of people successfully living out our values. This is a great way to reinforce them and encourage the team to do the same.

Steer away from failure

Call out examples of where values are not being followed. Exactly how you do this will be guided by your values themselves. My approach is to be as public as possible. Feedback in public is powerful as it is a signal to the rest of the team that you are serious, and they get to see your most important job, which is to make sure the culture is what you say it is. Your culture is what you tolerate.

I do this very carefully as gentle reminders, and wherever possible make sure it is not personal, and frame it as a question: eg “is that approach really working in plain sight?” or “could we publish the plan before starting the work?” if the values are discussed regularly enough, then a very gently reminder is all that is needed.

For more serious issues, you can give private feedback. Having these kinds of crucial conversations is another topic.

Hire for values not just competence

Values become especially critical during hiring. Every member of your interview panel should be testing for cultural alignment, particularly with core values. While candidates don’t need to match every value perfectly, they must align with your core values.

Structure your interview questions specifically around your company values. This allows you to systematically evaluate cultural fit and gives candidates clear insight into what matters to your organization.

Have each interviewer on your panel focus on evaluating different core values. This approach ensures comprehensive coverage of all values and prevents redundant questioning while giving you multiple perspectives on cultural alignment.

Look carefully for evidence that candidates have demonstrated your values in their past experiences and behaviors. Ask for specific examples and dig deep into situations where they’ve shown alignment with your core principles.

Don’t be afraid to reject technically strong candidates if they don’t align with your cultural values - skills alone aren’t enough. A misaligned hire can damage team dynamics and culture, even if they’re exceptionally skilled at their technical role.

Teach value-based decision making

Decision making at all levels should be guided by your values. Use them as a framework for decisions and reference them explicitly when explaining choices to the team. Be willing to take hard stances based on core values, even when it is difficult. This demonstrates your commitment to the culture you are building.

If the team learns how to make decisions using values, they will be able to make better decisions faster. This will compound over time, creating exponential returns as your organization grows. They are a multiplier for your organization’s effectiveness by enabling faster decision making and more autonomous teams as everyone learns to act as one.

The key is to keep your core values few, make them meaningful, and live them consistently. Your team should know them so well they can repeat them like a mantra - even if they roll their eyes while doing so.

Avoiding bad startup culture is a little and often process. Start early, be intentional, and remember that figuring our a first draft of your values is just a starting point. The living out of your values is what makes the culture real, and not the tangled mess of poor culture that knaws at the roots of what you’re building and has the potential to bring it down.

There is never a more impactful time to shape the way your company works than now. Like a great garden, a good culture is a thing of beauty. Your organisation will get smarter and more healthy over time without needing your involvement. You will help your team do the work of their lives, and make their work experience a joy. I can think of few better reasons to work on your culture than that.