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LeadershipAdvice

Ask a CEO coach: ‘I’ve always been a high achiever, but what’s holding me back from becoming a leader?’

By
Bill Hoogterp
Bill Hoogterp
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By
Bill Hoogterp
Bill Hoogterp
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March 7, 2025, 5:00 AM ET
Executive coach Bill Hoogterp weighs in on what we want from leaders.
Executive coach Bill Hoogterp weighs in on what we want from leaders.

Bill Hoogterp is a bestselling author, an entrepreneur, and one of the top executive coaches in the world. 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 answers real questions from executives striving to become be better leaders.

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The subject of this week’s conversation is Lina, an executive in the finance sector in her thirties who is wondering why she feels stuck. The skills that propelled her to top reviews for years suddenly aren’t working as well to get to the next level of leadership. While attending a company training, she has a seemingly simple question for Bill: Why?

BH: My time is your time; how can I be helpful?

Lina: How can I improve more? What do I need to work on?

BH: Why do you want to?

Lina: You saw me in the training; I’m doing well, but I want to get to an even higher level.  

BH: Yes, I get that, but why?

Lina: Well, doesn’t everyone?

BH: No, but even if they did, you still didn’t answer, why do you?

[Long pause]

Lina: I don’t know. I guess I’ve always just strived for the highest I can.

BH: Lina, I am pushing you because I can see everything you just said, I saw it all morning, but it will help you to understand more your own why. But I can tell you something. Direct questions deserve direct answers. I noticed one thing about you.

Lina: What’s that?

BH: You try really hard to win people over.

Lina: What’s wrong with that? Is that bad?

BH: No, but I’ll tell you a CEO secret. When you’re young, your job is to impress. Impress the boss.  Impress the peers. Impress the clients. Everybody has a role—that’s your role.

Lina: [Nodding]

BH: But as you move up now to a higher level, it’s not your job any more to impress people all the time.  Now it’s your job to be impressed.  To let other people impress you.

[Silence, quizzical look.]

BH: The higher up you go, the less you know, the less you do, the more you accomplish. You don’t have to be the smartest one in the room anymore. That worked to get you from here to here, but it won’t get you from here to there. You can’t out work or out-clever everyone at this level. Jedi mind tricks don’t work on other Jedis. But the good secret is…you don’t have to.    

BH: Let your teams come up with better plans than you did; that’s what you pay them for. Once in a while, the boss and clients actually do see things you don’t see yet. Let them share their insights.  It makes them feel good. When you give up the need to impress people all the time, and let them impress you, you get promoted from…smart…to…wise. Lina, I know this is corny factor 11, but take this scrap paper and write on it “need to impress.”  

Lina: [Writes]

BH: Now crumple it up, come stand here, and hold it tight in your hand over the can. Lina, that need you are holding is healthy, natural, and normal. You have been doing it right and doing fine and now you just have one thing left to do. Let it go. And see what happens.

To learn more about Bill, visit lifehikes.com. To submit a question 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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