10 Tactics To Find Startup Culture Fit

People look for their next startup role for 3 main reasons:

1. Seeking more growth and opportunity

2. Transitioning into something they’re excited about

3. Escaping a bad manager and toxic culture

Lately, I’ve heard a lot of people citing the third reason.

Just this week I spoke to three people who worked super hard and drove great results but left the company on their own accord due to the conditions getting so bad they just couldn’t take it anymore.

If this sounds like you or if you want to be thoughtful about the culture of your next startup, you’re in the right place.

This week, we’ll cover:

• Why a startup’s culture is crucial to your overall experience and success

• 10 tactics to get a real picture of the company’s culture

What You Do Is Who You Are.

Ben Horowitz, Co-Founder of top VC firm Andreessen Horowitz, wrote a book titled, “What You Do Is Who You Are.” It’s a must-read for anyone in startups and any current or aspiring manager or founder.

The title says it all. A company’s culture isn’t defined by the lofty statements it shares on its website or in founder podcast interviews. It’s what they actually do, day in and day out.

And more than anything, it’s what they do when times are tough.

Crisis and Culture.

When revenue is soaring and customers are happy, it’s easy for everyone to get along. But, the real essence of an organization’s culture is revealed in crisis.

Crisis, my friends, is why culture is far more important to focus on in a startup than in a large corporate company. The earlier you join a startup, the more that crisis (or apparent crisis) will be your constant companion.

Before you get to the gold-drenched halls of a Series C where the business model is figured out, product-market fit has been achieved, and you just need to pour gas on the fire to turn the company’s spark into an inferno, you must first pass through the gauntlet of Pre-Seed, Seed, Series A, and Series B. In those early stages, because the company is so small and still trying to figure things out, many things can seem like (or actually are) an existential crisis to its survival.

How a company handles these challenges shows its true character.

Are they cool, calm, collected, principled, and collaborative under pressure, helping each other make quick decisions, supporting them to try new things, treating failure as an opportunity to learn how to make the company better, and disciplined about documenting those best practices so they don’t repeat the same mistakes twice?

Or, are they frantic, random, inconsistent, prone to inner team arguments, focusing more on who it was that led the company into a situation of crisis so they can be reprimanded and made an example out of?

Regardless of which side of the line the company falls on, it pays to have as much information about the culture as possible because it will either lead you to do the best work of your life or leave you miserable.

Culture Change.

An unspoken aspect of culture is that while not impossible, it is very hard to change it as a single person.

Typically when you join a startup, they have had years of operating in a given way. The founders will have their own way of doing things. They are the boss and the main driver of the company culture.

If they don’t want the culture to change because they believe it has served them and the company to this point, then you, as a single individual, are not going to be able to change it.

So, unless you want to try and push a boulder up a hill to change the culture while doing the challenging work of building a startup - I’d recommend doing the work to find a company with a culture that matches what you’re looking for.

Culture Explorer.

So, how do you uncover the authentic culture of a startup before you sign your offer and embark on the incredible but challenging voyage of company creation?

Here are 10 ways.

1. Ideal Company Characteristics: Before you apply for your next role or send off that first networking message, press pause and do the work to understand what you want in a company. Make a list of all the previous companies you have worked for. Write down all the aspects of that company’s behavior and culture that you enjoyed and set you up for success and all the aspects that led you to be miserable. Be as specific as possible. You now have a list of company characteristics to move towards and run away from. Next, take those characteristics and craft questions around them (or have ChatGPT help you craft questions around them) ahead of time so you can ask multiple people the same set of culture-based questions and see how similar or different their responses are. A good company culture will result in the majority (if not all) members of the company giving you the same response.

2. Current Employee Interviews: When people build their startup job search strategies in the Early Accelerator they don’t just reach out to the hiring manager and recruiter. They reach out to 10-20 people on the team. Most of these people are outside of the interview process and that’s a good thing. You’re looking to speak with people who are currently on the team you’re looking to join, cross-functional stakeholders you will work with, and leaders in critical departments. If they’re not involved in the interview process they’ll be more likely to give you their “no-bs” assessment of their experience in the company and what it actually looks like inside. Ask the questions you came up with when crafting your “ideal company characteristics” but remember to ask if they can provide you with a specific example of a time the company was in crisis and how the team handled it. I also like to ask if those crisis moments happen once a quarter or once a week.

3. Former Employee Interviews: The people who are going to give you insight into how these people operate are those who have already worked for/with them. If the founders of the startup have started other companies, reach out to former employees of those other companies and ask them about working with the founder and how they handled the crisis moments. If they say they would 100% work for the founder again, ask them why they’re not currently working with them. You can also reach out to former employees of the company you’re looking to join. There is no downside to contacting these people so reach out to as many of them as possible and try to get up to 6 different people’s feedback. The more people you’re able to speak with, the better chance you have to get a distributed average position instead of the position of one disgruntled low-performing employee.

    

4. Research Leader Behavior: Do a quick Google and Reddit search for the leaders in the company to see if any flags pop up. A member of the Early community was interviewing with a Seed-stage company and found a blog post written by a co-founder who had been fired. The co-founder who had been fired had some not-so-nice things to say about the other founder and the company. The member was able to get in touch with the former co-founder and when she interviewed with the founder was able to bring up the blog post to hear the response and explanation directly from them.

    

5. Evaluate Company Policies: If you’ve received an offer, ask for the policies and benefits details. If you’re pre-interview or in the interview process and the company has a page on its website describing its policies, do a deep dive and see if those policies match your values. If their policies aren’t public, ask about them when having conversations with members of the team. Remember, the culture of the organization is not what is listed on a piece of paper, it’s how the people in the organization act. They can have an unlimited vacation policy but everyone you speak with hasn’t taken a day off in over a year. Ask people what it looks like in practice.

6. Read Online Reviews: Depending on the size and stage of the startup they may have reviews on GlassDoor, Blind, or other review sites. I always take these with a grain of salt because very few people who are having an amazing experience at a company feel the need to share that with the internet. Those who have had a terrible experience or feel they have been wronged in some way are very vocal. So, take the reviews as a data point you can ask questions about in conversations with people at the company. Don’t be afraid to reference these in the question period in your interviews. Do it in a thoughtful way that shows you did your research and are approaching it from a position of curiosity vs accusation.

7. Observe the Office Environment: In an ideal world, you’ll be able to come into the office to meet and see the team in person. If you’re able to do this, what are the vibes like? Are people joking around? Do you see people who look like you? Does it seem that they care about the same things you care about? This is more challenging for remote teams because the likelihood of them allowing you to sit in on a company meeting or access company communications is practically zero.

8. Speak With Investors: Depending on your seniority you may be able to get in touch with investors in the company. If possible, ask about what led them to invest and the things they think the founder is doing particularly well, what the company does well, and what the company needs to work on. Then ask them about any challenges with the founder and current team. Most VCs are founder first, so they may not give you the full open, and honest answers but depending on the rapport you build and what you’ve done in your career, you might be able to gather great insight.

9. Ask Specific Questions in Interviews: Ask your culture discovery question in the interview. This is a captive audience and they’re giving you a chance to ask them what it’s actually like to work there in the interview process so don’t shy away from the opportunity. Ask about the crisis scenarios, how the company handled them, and how often they happen. Ask the questions that will help uncover the specific cultural details that set you up for success or created a terrible work environment in the past. If you get an offer and you’re still deciding, ask to set up additional time with any interviewers you would like to dive deeper with.

10. Check for Cultural Fit: Once you have all this information you will need to determine if your personal values and working style align with what you’ve learned about the company culture. If you’re doing this on the fly, you’re going to set yourself up for failure. That’s why it’s important to do the work I described in number 1 before setting off on this journey of cultural discovery. That way you have a rubric to grade against and determine if this company is a “hell yeah” or a “no”.

The first day I walked into the shabby Uber office in Queens in 2013 I knew it was a culture I wanted to be a part of.

People laughing while they were hard at work. There was music playing, the energy was high, and I could see the constant collaboration between team members. From sitting in on a single driver onboarding I could see the level of analytical rigor and documentation that found its way into every aspect of the business.

No one seemed to care that there weren’t enough desks or that the horns of taxis outside sometimes blared for a full minute. People were wearing T-shirts and shorts. There were men and women, people from different backgrounds, all working together on a shared mission. It was far different from the suit-wearing, stuffy, Fortune 500 cubicle environment I was running away from and exactly like the work environment and culture I was looking for.

That environment led me to learn more than I would have in any MBA program and do the best work I had ever done.

Finding a startup with a culture that fits your values is critical for your success and fulfillment. You are going to spend more time with this company than with your own family and you’ll be dedicating years of your life to helping them win.

Using these tactics will uncover the true culture of any startup before you join and can make all the difference in your career journey.

Let’s go get you that job 🏆

Kyle