Sin 01
Focusing on the wrong things
A CEO's main focus should be company strategy and overall health - anything related to keeping the company going and having a future: raising money, ensuring there is a clear product strategy, addressing critical operational challenges.

Often founders focus on the wrong things or on minor issues. Sometimes this happens with controlling or micromanaging founders who struggle to let go of what they used to do themselves. A former engineer who steps in to fix bugs and feels good after shipping something quickly is not doing their job as CEO - they are doing someone else's job and neglecting their own. Reaching for low-level tasks because they feel manageable is a very human response. It is also a very costly one.

Another version of this is the CEO who is convinced they are simply better than their team at a particular skill. I worked with a CEO who was certain he was better than anyone on his team at persuading talented people to leave well-paid stable careers for his startup. The underlying belief - "if it was me it would have been done long ago" - is almost always a distortion. The founder did those things when the company was 10 people. The company is now 100 people, and the complexity of operations has grown in ways the founder often does not account for.

With less experienced founders, there is a third pattern: freeze. Faced with a problem they don't know how to solve, they gravitate toward problems they do know how to solve. If you know nothing about building a spaceship but are assigned to build one, you will naturally spend a lot of time discussing the color of the frame. Because that is what you know. As a CEO, you should always know what is worth your time - and be honest with yourself when you are avoiding what is not.

Example If your company is failing and you are asking your employees to change the name of the meeting - this is a waste of your time. Your task is to keep your company going. If you are actively investigating why a watercooler or printer is not working in the office while your company's runway is less than 3 months - you are wasting your time. The watercooler will not matter at all when your company is shut down. Naturally people get annoyed when something is not working as they want. Everything will not work as you want it to, even if your employees work 24/7 - get over this.
Sin 02
"I am a genius, that's why this company succeeded - so I know everything better"
Yes, you might be a talented CEO with a good idea. But the right market fit, timely funding, the right connections, and talented people who worked alongside you since day one all contributed massively to that growth.

Attributing success entirely to yourself is not just inaccurate - it is dangerous. It leads to dismissing input, undervaluing the people around you, and making decisions without the information you need. You should always hire people who are smarter than you in their domain. A CEO who is the smartest person in the room has hired wrong.

Sin 03
"I don't want to mediate relationships between my executives - they should work well together and sort things out on their own"
Wanting your team to sort things out on their own is not a leadership style. It is avoidance - and it usually comes from founders who want to be liked and are afraid of making people (or herself/himself) uncomfortable.

Your executive team should be in no doubt that their goal is to make the company successful - not to protect their own territory. When that stops being the case, it is the CEO's job to name it and address it directly.

Example During an on-site meeting, two executives started arguing over ownership of a team. They fought for 2 hours over whether employees should be assigned to one or another. The CEO was listening and addressed the tone but did not address the issue. If your executive team fights for influence - I have bad news for you. They are not focusing on the company's success. They are only interested in their own benefit.

The CEO should steer the conversation back on track and make clear to both executives that power fights are not a productive use of anyone's time. And it will never be tolerated.

When should the CEO intervene and when not? Executives should be able to handle most things together. But if peer feedback is consistently being ignored by one or both sides, that is the moment for the CEO to step in. You cannot opt out of this entirely and call it trust.
Sin 04
"These people were with me since day one - I trust them so they should stay in the company forever"
As the company grows, neither you nor the people who started the company with you may be the right employees to keep.

You will see a lot of startups with employees who have worked there for 8-10 years. The worst setup is when those people have never worked anywhere else and have no industry experience outside of what they built with you.

Example Imagine a team of 10 engineers who started with an tech startup. There was one engineer who was the best among those 10. Of course he would be promoted to senior engineer, then domain lead, then director. The company grew to 60 engineers. Is that person still the most talented? No - but the organization is so biased by early evaluations that it fails to recognize there are better people for the role. What happens with the more talented engineers? They see that there are no prospects and leave. What happens a lot is the "best" engineer makes very suboptimal decisions as they have only dealt with an older stack and smaller infrastructure. They have never had experience working with larger traffic and thus make suboptimal decisions. Good if they listen to other engineers who actually have industry experience. What happens more often is that people in these "best employee" seats develop massive ego issues and do not listen, because they think they know better.

The best people always have the most options. If the company is doing nothing to develop or retain talent, the best people are the first to leave. We can talk a lot about loyalty, but nobody will stay in a company with no career progression and poor pay simply because they like the founder. If they do stay - it most likely means they have nowhere better to go. Do not let your ego convince you otherwise.

People also simply get tired. Someone who gave everything in year one will not sustain that indefinitely, nor should they be expected to. Keeping someone who is no longer performing out of loyalty is not generosity - it is actively demoralizing to everyone working hard around them.

Sin 05
Ego traps
One of the most surprising things is hiring and keeping people the CEO has a good relationship or vibe with - but who are not right for the job.

The pattern works in both directions. The moment friction appears with an executive, the CEO writes them off. Meanwhile, executives who are easy to be around get away with repeated underperformance - because the CEO enjoys the relationship and finds reasons to justify keeping them.

The rule If your reasoning for hiring someone is "I had a great conversation over lunch with Greg" - make Greg your friend and hang out with him. Do not hire him into your organization. Relationships with your executives can be hard. If they deliver, that is what matters. Focus on the company, not on your comfort.

Always use external metrics to evaluate your executives - not internal ones. Compare against what is standard in your market. If you run a customer support team, look at cost per agent, response time, and ticket resolution time against industry benchmarks.

If your executive reports a 40% improvement compared to how things were before they joined, ask yourself what that baseline actually was. A 40% improvement on a very poor starting point may still be well below what any comparable company is achieving.

Sin 06
Listening to the loudest executive
People on your team will have different personalities. Not everyone will be loud and extraverted. Some executives are naturally reserved and quiet - often they have the best ideas.
Example I worked in a team where there was an executive who was extra focused on showing their results. Often times results were overestimated or phrased in a way that made them sound big and important, while in reality they did not even make sense to spend time on. The CEO was so persuaded that this executive was good at everything that they ignored plain facts and numbers. Moreover, the whole executive team had heard so many times how great this executive was and how "no matter what they touch it works" that they were all sure this person was the best performer. The reality was this person was loud and occupied most of the time in executive meetings.

You want to separate what people say about themselves from what they actually deliver. No executive will ever tell you they failed a project or wasted the company's time. Everyone presents their work in the best possible light, especially if this is what you encourage. Quantify the results your executives bring. Their job is to work together to make the company better - not to compile an impressive-sounding list of activities for the weekly meeting.

If your executive has never once admitted to making a mistake, ask yourself whether that is actually possible. Startups require failing fast in order to learn. An executive who has never failed at anything is almost certainly someone who is more focused on protecting their image than on the company's progress.

The rule It is your role as CEO - or your Chief of Staff's - to make sure every executive has time and space to speak. The moment one person is talking 80% of the time, you have a problem. Even - and especially - if that person is you.