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The Long Way Around

What I Learned Coaching 100 First-Time CEOs

Apr 10, 202646 min7,340 words(37 min read)
If you only read one thing
  • 1This is your highest-performing episode for actionable insight. A grade across the board.
  • 2Your guest's '90% of CEO problems are loneliness problems' line is your single best Short. Ship it twice.
  • 3Listeners are asking for a worksheet of the questions she uses with her CEOs. Make it.
  • 4Schedule a follow-up specifically on the CEO who asked her if it was okay to cry at work.

Shareable moments

16

The best lines and clips — ready to copy, caption, and post.

Best for: This episode is a Shorts goldmine. Five of the seven candidates above are independently strong. Ship them across two weeks for sustained promotion.

  • 1
    Clip18s

    90% of CEO problems are loneliness in disguise

    Ninety percent of the problems first-time CEOs bring me aren't strategy problems. They're loneliness problems wearing a strategy costume.

    Opening hook

    Ninety percent of CEO problems aren't strategy problems.

  • 2
    Clip14s

    Stop trying to look like a CEO

    The best CEOs I've worked with all have one thing in common: they've stopped trying to look like CEOs.

    Opening hook

    The best CEOs all have one thing in common: they've stopped trying to look like CEOs.

  • 3
    Clip22s

    The CEO who asked if she could cry at work

    A CEO once asked me if it was okay to cry at work. I asked her how often she cried at work. She said never. I said that's the problem.

    Opening hook

    A CEO once asked me if it was okay to cry at work.

  • 4
    Clip20s

    Three questions for every new CEO

    I ask every new CEO three questions: who are you scared of, what are you avoiding, and who knows you're scared. Those three answers tell me everything.

    Opening hook

    I ask every new CEO three questions.

  • 5
    Clip16s

    The smallest gap wins

    The founders who survive aren't the smartest. They're the ones who develop the smallest gap between what they think and what they say.

    Opening hook

    The founders who survive aren't the smartest.

  • 6
    Clip18s

    The trust diagnostic

    I had a CEO tell me his board didn't trust him. I asked him to list five times he'd told the board something hard. He couldn't list one.

    Opening hook

    A CEO told me his board didn't trust him. I asked him to list five hard truths he'd told them.

  • 7
    Clip22s

    Find someone two years ahead

    If you're a first-time CEO, the best thing you can do this week is find one peer who is two years ahead of you and pay them whatever they ask for an hour of their time.

    Opening hook

    The best thing a first-time CEO can do this week.

  • 8
    Counterintuitiveearly

    Ninety percent of the problems first-time CEOs bring me aren't strategy problems. They're loneliness problems wearing a strategy costume.

  • 9
    Insightmiddle

    The best CEOs I've worked with all have one thing in common: they've stopped trying to look like CEOs.

  • 10
    Storymiddle

    A CEO once asked me if it was okay to cry at work. I asked her how often she cried at work. She said never. I said that's the problem.

  • 11
    Emotionallate

    Every founder I've ever coached has a moment where they realize the company they built is also building them. Most of them are not happy with what's being built.

  • 12
    Actionablemiddle

    I ask every new CEO three questions: who are you scared of, what are you avoiding, and who knows you're scared. Those three answers tell me everything.

  • 13
    Insightlate

    The founders who survive aren't the smartest. They're the ones who develop the smallest gap between what they think and what they say.

  • 14
    Storylate

    I had a CEO tell me his board didn't trust him. I asked him to list five times he'd told the board something hard. He couldn't list one.

  • 15
    Actionablelate

    If you're a first-time CEO, the best thing you can do this week is find one peer who is two years ahead of you and pay them whatever they ask for an hour of their time.

  • 16
    Counterintuitivelate

    The hardest thing I do as a coach is convince a successful CEO that they're actually allowed to be confused.