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LeadershipAdvice

Ask a CEO coach: ‘Am I too nice?’

By
Bill Hoogterp
Bill Hoogterp
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By
Bill Hoogterp
Bill Hoogterp
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March 23, 2025, 12:07 PM ET
Illustration by Fortune

Bill Hoogterp is an author, entrepreneur, and one of the top executive coaches worldwide. He has advised dozens of Fortune 500 CEOs, and last year his company LifeHikes offered trainings at more than 100 global companies in 47 countries and seven languages. In this series for Fortune he has coaching conversations with real executives striving to become better leaders.

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The subject of this week’s conversation is Dave, head of strategy in his 30s for a large consumer products company whose boss said could be more “bad a**.”

Bill: My time is your time, how can I be helpful?

Dave: I got some surprising feedback from my boss. He is not the first to say it, but generally, that I don’t come off as… well, that I come off as serious but too nice.   

Bill: What do you think?

Dave: He said I should still be a good guy but sometimes you have to be a bad-a**.

Bill: Oh, this is very interesting. Say more. Start with what you want to be more of?

(Long pause)

Dave: I would like to be a stronger leader. Higher level executive. And I know they are tougher and have more gravitas and air of authority.

Bill:   How do you think people see you now? If I pulled in a few of your peers and said, ‘hey, what’s the story on Dave’ what would I hear?

Dave: Probably, he is smart. Helpful. Nice guy. Always looking to be a good colleague.

Bill: Sounds like good qualities to be known for.  What is missing?

Dave: Being able to be tough. To say no. To be more decisive.

Bill: OK, I’ll give you a choice of a golf or music analogy?

Dave: Music

Bill: Name an instrument you like in an orchestra.

Dave: Violin 

Bill: So all songs can done with just violins?  It’s such a good instrument.

Dave: No, you need different ones for different sounds.

Bill: Your full leadership is the orchestra. Becoming your best song requires many aspects of your best self. There are many facets to the diamond that is you. Most of us have a few parts of our personality that we show at work. But usually just those. We have our “go to” moves that work for us, have always worked, but are still only part of what we could be. Growth means expanding and getting out of your comfort zone and developing more aspects of who you are and doing it publicly.  Letting new instruments join your song.

Bill:  OK, that feels theoretical. Let’s try something different. Come step on my foot.

Dave: Gently steps on my foot.

Bill: Step on my foot.

Dave:  Steps on my foot.  (A bit firmer,, not much)

Bill: Dave, step on my foot!

Dave: Steps a little bit harder (this request and action repeats 4 more times before he finally pushes really hard).

Bill: Why did it take 7 times before you pressed hard enough for me to feel pain?

Dave: I didn’t want to hurt you.

Bill: That’s you. That is your problem. Your first lens is not to cause discomfort. In your annual review I bet when they ask you are always collaborative your rating is no conflict with anyone. As your coach, I don’t love that. That shows you are too nice. I am not saying stop being who you are or be mean on purpose, but focus more on getting things done as lens one.  Choice of two more analogies, basketball or dancing?

Dave: Dancing.

Bill: You and your spouse/partner ever go to a wedding where there is dancing?  (nods, yes). OK, you’re dancing and you accidentally step on someone’s foot, what do you do?

Dave: Say sorry.

Bill: Then they hit the alarm, call off the rest of the reception because you did that, everyone goes home?  Dave, what is the 100% guaranteed way to make sure you never step on toes when you dance?

Dave: (Thinks for a while). Don’t dance.

Bill: I can see why you’re head of strategy. You got it quick. So I’ll tell you what you already know. In the dance of real business, things move fast. You gotta move faster. The market is changing. You have to change faster. Conditions are challenging, you have to be more aggressive than the problems arising. And if you are doing it right, sometimes you step on toes and sometimes people step on yours.  Not to hurt, but just because you are dancing at a higher speed on a more slippery floor. The higher up you go, the feet get heavier, not lighter. Say sorry and keep dancing. 

Dave: I’m going to remember stepping on your foot for a long time. I got the message.

To learn more about Bill, visit lifehikes.com. To apply to have Bill coach you for a future column, email bill_hoogterp@lifehikes.com.

Join us at the Fortune Workplace Innovation Summit May 19–20, 2026, in Atlanta. The next era of workplace innovation is here—and the old playbook is being rewritten. At this exclusive, high-energy event, the world’s most innovative leaders will convene to explore how AI, humanity, and strategy converge to redefine, again, the future of work. Register now.
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