26 DAYS AGO • 4 MIN READ

The BIGGEST signs your culture isn’t what you think!

profile

100 CEOs

Imagine if you could be personally mentored by some of the world's greatest CEOs that are alive today and they personally answer whatever question you are struggling with in your journey. This is how 100 CEOs was born - a newsletter where some of the world's biggest CEOs and entrepreneurs answer questions that you want to hear. If you're ready to receive actionable advice straight to your inbox, enter your email and we’ll handle the rest.


Responsive Header

What’s the biggest sign that a company’s culture isn’t what leadership thinks it is?

I asked 100 CEOs this question and here are the top 5 answers:


Steven Bartlett, Founder of FlightStory, Thirdweb, The Diary Of A CEO & Investor in more than 50 companies.

A company’s culture is nothing more - and nothing less - than the behaviours people display and the decisions they make when nobody is watching. Those choices are shaped by a web of incentives, spoken and unspoken, that the company intentionally or accidentally creates.

Culture is healthy when the team’s decisions match the behaviours the company claims to value; it breaks the moment those decisions drift. My earliest warning sign is repetition: when I find myself reminding teams again and again to act with a behaviour we desire; urgency, kindness, agility or customer obsession, I know the issue is no longer their memory - it is the system I have built.

When I fall into this loop, instead of issuing yet another plea, I pause and ask: what incentives in this environment make the desired behaviour hard and the undesired behaviour easy? By increasing the psychological incentives for the right actions and stripping away the disincentives, the behaviour sticks without further prompting.

In short, if you keep having to ask, fix the system, not the people. Giving out orders will help you win once, but creating a strong culture will help you win repeatedly.


Jaspreet Singh, CEO of Briefs Media and creator of Minority Mindset, with more than 4 million followers online.

"Culture starts at the top. I wanted to be liked, and I thought if people liked me and were having fun - it must be a great business.

I was wrong.

In the early days of Briefs Media, we hired people we thought were creative. We [prided ourselves on] being a ‘fun place to work’. The problem? Nothing was getting done. We weren’t working to succeed - we were working to have fun.

I wasn't building a company culture, I was building a failing company.

That's when things changed. We set new goals, KPIs and protocols and created a values guide. We asked everyone to return to the office so we could build the best possible version of the company.

It was a major shake-up. We went from chasing fun to wanting to build a real, profitable business.

Over 14 months, we rebuilt the team - now, every new hire goes through a 90-day value training to understand why our culture matters.

Culture starts from the top, but then it spreads from everyone else."


Eric Partaker, Founder of The CEO Accelerator, author and entrepreneur.

"Culture is what happens when you're not in the room.

A CEO I coach recently attended a week-long conference. When she returned, standards had slipped, deadlines had been missed, and accountability had disappeared. She was shocked… until I pointed out the uncomfortable truth: you don’t have a culture - you have a dependency.

The biggest sign that your culture isn’t what you think it is? It disappears when you’re not around.

True culture isn’t spoken; it’s lived. It’s in how your team behaves when nobody’s watching. If you see performance or behaviour gaps when leadership steps away, you're looking at a culture gap.

How do you close the gap?

  • First off, role model the behaviors you want to see. Don’t expect reliability if you’re unreliable yourself.
  • Secondly, run a simple anonymous survey with just one question: “What are the unwritten rules here?”

The difference between the answers and your official values will shine a spotlight on your culture gap."


Victoria Prew, Founder and CEO of HURR, Investor, and Forbes 30 under 30 alumni:

"There’s a big difference between people doing the job because it’s expected, and doing it because they actually believe in the mission. This disconnect often starts at the top.

Founders and CEOs tend to assume everyone’s rowing just as hard as they are. After all, the vision is exciting, right? But most employees aren’t owners. They don’t have the same financial upside, and they’re not rewarded for carrying the emotional weight of the company. Expecting 100% from someone who's not structurally set up to care that deeply isn’t just unrealistic, it’s also unfair.

Effective leaders don’t force founder-level buy-in. They build the bridge by focusing on:

  • Communicate the “why” relentlessly, not just the “what”.
  • Align incentives and recognition with what they truly value, whether that’s innovation, collaboration, or long-term thinking, not just hitting targets.
  • Create psychological safety so people feel empowered to question, contribute, and push back.

That’s what builds a culture people want to be part of, and stay part of."


Andrew Henderson, Founder and CEO of Nomad Capitalist.

"When leaders talk about “trying their best” instead of getting results. Culture is built when expectations are non-negotiable.

If you’re talking about culture but not enforcing it, you don’t have one. It took (...) running businesses across four continents to realize culture isn’t written in a handbook. Culture must be reinforced every day.

We fill out 47-page forms no one else wants to touch. That’s culture. And even then, it’s not perfect. [At one point] people cared too much, and they started letting others walk over them. Once we established a culture of hyper-caring, we had to go in and pull it back in the right places.

If you’re letting people miss deadlines, overlook details, or hide behind ‘trying’ - you’re not building excellence, you’re building comfort."


WHAT QUESTION DO YOU WANT ME TO ASK 100 CEOS NEXT?

I read every single message and your input shapes this newsletter - click the button below to let me know below.

Talk soon,

Steven

73 Cornhill, London, EC3V 3QQ
Unsubscribe · Preferences

100 CEOs

Imagine if you could be personally mentored by some of the world's greatest CEOs that are alive today and they personally answer whatever question you are struggling with in your journey. This is how 100 CEOs was born - a newsletter where some of the world's biggest CEOs and entrepreneurs answer questions that you want to hear. If you're ready to receive actionable advice straight to your inbox, enter your email and we’ll handle the rest.