The Leadership Question: Navigating Your Trail

Brian Wygle

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.

Episodes

  1. 6d ago

    Having The Right Answer or Asking The Right Question? — Mike Ryan | The Leadership Question

    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

  2. Oct 12

    When does a good leader know it is time to get out of the way? — David Levian, Break Room Therapy

    When does a good leader know it is time to get out of the way? David Levian has spent 23 years coaching girls’ softball. He also co-owns Break Room Therapy outside Grand Rapids, Michigan, with his wife, Dawn. On the field and at work, his goal is the same: help people grow into leaders, then step back and let them shine. This is one of three independent answers to the same question. The other guests never hear his. What you’ll hear: Why he hands people decisions before they feel readyHow he reads confidence in a voice, a posture, and a look in the eyeThe staged way his team learns: shadow first, then leadWhat happened when his young staff had to run the business without himWhy empathy is at the heart of good leadershipHow every person can lead in their own way, even if it’s not up frontAbout 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 David Levian: Website: breakroomtherapy.comLinkedIn: linkedin.com/in/david-levian-8bb42613Instagram: @breakroomtherapyConnect with Brian Wygle: Website: helpformycompany.comLinkedIn: linkedin.com/in/brianwygleInstagram: @helpformycompanyTimestamps: 00:00 The question: When does a good leader get out of the way? 02:27 David Levian: Reading confidence in a voice and a posture 04:51 David Levian: When the team had to step up 06:03 David Levian: Meeting every customer where they are 07:14 David Levian: Making people feel welcome and safe 08:05 David Levian: “You’re creating better people” 08:26 David Levian: Raising the next generation of leaders 09:05 David Levian: Training shifts and spotting future leaders 10:03 David Levian: Everyone can lead in their own way 11:17 Closing: What’s your answer? #Leadership #LeadershipDevelopment #SmallBusiness #BusinessOwner #Coaching #DevelopingLeaders #TheLeadershipQuestion

About

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.