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The Leadership Question: Navigating Your Trail

The Leadership Question: Navigating Your Trail

By: Brian Wygle
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The Leadership Question: Navigating Your Trail is a podcast for business owners who are tired of getting advice from people who've never actually sat in the chair.

Every episode, three business leaders answer the same question — completely independent of each other. They don't hear the other two answers. They don't compare notes. Their three answers get combined into one episode, so you hear three honest, unscripted takes on the same question, side by side.

There's no debate and no scorecard. Nobody's trying to win. The point isn't which guest gave the best answer — it's the question itself, and what it reveals that three people, on three different trails, land in three different places.

Host Brian Wygle opens each episode and explains why the question matters. Then he gets out of the way. The guests do the talking. He closes with one observation and hands the question back to the listener: what would your answer be?

Brian spent 40 years as a CEO, investment banker, and turnaround advisor across five industries. He's not a consultant working from a textbook — he's made the hard calls himself, more than once, and come out the other side. "Some people start things. Some people grow things. Me, I fix things" is how he puts it.

Every leader is on a trail. Start-Up, Growth, Stability, Turnaround, or Exit — five stretches of ground, and each one asks something different of the person leading it. What gets you through one trail won't get you through the next. The questions on this show come from that idea: where you are changes what you need to know.

New episodes post when they're ready, not on a forced schedule. Hear all three perspectives, then ask yourself the question — and figure out which trail you're on.

2026 Brian Wygle
Economics Leadership Management & Leadership
Episodes
  • Having The Right Answer or Asking The Right Question? — Mike Ryan | The Leadership Question
    21 Oct 2026

    What is more important in a leader: having the right answer or asking the right question?


    Mike Ryan spent decades as an investor. He was a partner at Goldman Sachs and managed about $18 billion for the Harvard University endowment. Today he is founder and CEO of BulletPoint Network. Brian Wygle asked him one question, and Mike answered it on his own, without hearing the other guests.


    What you'll hear:

    • Why a team can make great time and still be going in the wrong direction

    • Why fast, confident answers make the right question matter more, not less

    • The difference between expertise and judgment, from the basketball court to Wall Street

    • Why the best leaders try to kill their own thesis every day

    • Why changing your mind is not weakness


    About Brian Wygle

    Brian Wygle has spent 40 years as a CEO, investment banker, and turnaround advisor across five industries. He has sat in the chair, made the hard calls, and come out the other side. He is the author of nine books, including Leadership on Loan and the Five Cycles Leadership Series, and the owner of Help For My Company in Burbank, California.


    About the show

    The Leadership Question: Navigating Your Trail asks experienced business leaders one worthwhile question and lets each of them answer it their own way. Three perspectives on one question. No debate, no scoreboard. What would your answer be?


    Connect with Mike Ryan

    bulletpoint.network

    linkedin.com/in/mike-ryan-bpn


    Connect with Brian

    helpformycompany.com · linkedin.com/in/brianwygle · @helpformycompany


    Timestamps

    0:00 The question

    0:59 Mike Ryan: "We're going in the wrong direction"

    12:53 What would your answer be?


    #Leadership #DecisionMaking #BusinessLeadership #AskBetterQuestions #Judgment #TheLeadershipQuestion

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    14 min
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