Deep Leadership
Jon S. Rennie
Show overview
Deep Leadership has been publishing since 2020, and across the 6 years since has built a catalogue of 431 episodes. That works out to roughly 310 hours of audio in total. Releases follow a weekly cadence.
Episodes typically run thirty-five to sixty minutes — most land between 40 min and 46 min — and the run-time is fairly consistent across the catalogue. None of the episodes are flagged explicit by the publisher. It is catalogued as a EN-language Business show.
The show is actively publishing — the most recent episode landed 4 days ago, with 22 episodes already out so far this year. The busiest year was 2023, with 101 episodes published. Published by Jon S. Rennie.
From the publisher
“Leadership is a People Business.” That's the philosophy of this leadership podcast from Jon Rennie. It's real-world, actionable advice from Jon as well as his expert guests. As a former Cold War Submarine Officer who spent 22 years leading businesses in Corporate America before starting his own manufacturing business, he knows that leadership matters!
Latest Episodes
View all 431 episodes#0431 – Why High Performers Will Win in the AI Era (and Others Won’t) with Jacob Morgan
#0430 – The Networking Mistake That Could Cost You Your Career with Greg Roche
#0429 – Why Smart People Get the World Wrong with Peter Lamont
#0428 – Why Self-Awareness Is the Leadership Skill Most Leaders Lack with Margaret Andrews
#0427 – Leadership Decisions You Can’t Afford to Get Wrong with Dr. Linda Henman
#0426 – Stop Being the Fixer & Start Leading People with Robert Heath, Sr.
#0425 – Great at Your Job? That Doesn’t Mean You’re a Great Leader with Dr. Peter James
#0424 – Broken Trust: How Great Leaders Fix It with Dr. Darryl Stickel
#0423 – Claim Authority First – Then Figure It Out with Tom Kubiniec
Ep 422#0422 – Crisis Is Coming. Are You Ready? With Stephanie Craig
Crisis Is Coming. Are You Ready? Every leader will face a crisis. The question is whether you’ll be prepared—or caught off guard. In this episode of Deep Leadership, I sit down with Stephanie Craig, President of Kith, to talk about what most leaders get wrong about crisis management—and how to fix it before it’s too late. Stephanie shares why crisis preparedness is a mindset, not a checklist, and how trust, clarity, and communication determine whether your organization survives—or comes out stronger. We also dive into: Why most companies treat crisis prep like a “check-the-box” exercise The difference between your brand and your reputation (and why it matters) How to build trust before a crisis hits Real-world examples of companies that turned potential disasters into wins Practical ways small and mid-sized businesses can prepare without massive budgets If you lead a team, run a business, or want to become a better leader—this is a conversation you can’t afford to miss. Connect with Stephanie Craig:🌐 Website: https://kith.co📊 Crisis Resilient 365: https://crisisresilient365.com💼 LinkedIn: https://www.linkedin.com/in/craigstephanie/ Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 421#0421 – Stop Fixing Problems - Do This Instead with George Pesansky
Stop Fixing Problems! Most leaders are trained to hunt problems, fix issues, and eliminate failure. But what if that mindset is actually limiting performance? In this episode, Jon sits down with George Pesansky, author of Super Performance, to challenge the way we think about leadership, operations, and improvement. Instead of obsessing over what’s broken, George explains how the best leaders identify what’s working—and then scale it. You’ll learn: Why focusing on failure holds teams back The concept of the “Golden Hour” and how to replicate peak performance How leaders unknowingly create a culture of mediocrity Why your best people may be holding back (and how to unlock them) A better way to drive consistent, high-level results If you want to build a high-performing team, it starts with changing what you pay attention to. George Pesansky's resources: https://georgepesansky.com/ https://myblendedlearning.com/ https://amzn.to/4lJm4gU Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 420#0420 – The Success Trap: Why High Achievers Feel Empty at the Top with Keren Eldad
The Success Trap: Why High Achievers Feel Empty at the Top Success is supposed to make you happy… so why do so many high achievers feel trapped? In this episode of the Deep Leadership podcast, I talk with executive coach and author Keren Eldad about the hidden emotional cost of ambition. We explore why success and happiness often move in opposite directions, how leaders unknowingly build a “gilded cage,” and why perfectionism, hustle culture, and chasing the wrong goals can leave even the most accomplished people feeling empty. Keren shares practical insights on breaking free from the relentless pursuit of more, rethinking success, and leading from purpose instead of pressure. If you’re a leader, entrepreneur, or high performer who feels like your ladder might be leaning against the wrong wall, this conversation will challenge how you think about success. Learn more about Keren Eldad and her book Gilded https://amzn.to/4bqmRPaSubscribe to Deep Leadership for more conversations that help build a world with better bosses Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 419#0419 – The Confidence Trap: Why Great Performers Choke Under Pressure with Scott Papek
The Confidence Trap: Why Great Performers Choke Under Pressure Why do talented athletes, leaders, and entrepreneurs sometimes lose confidence in the moments that matter most? In this episode of the Deep Leadership Podcast, I sit down with mindset coach Scott Papek to explore why even high performers struggle with pressure, overthinking, and self-doubt. Scott works with athletes from middle school through college, helping them build the mental skills needed to compete with confidence. Together they discuss how confidence is actually trained, why negative self-talk and fear of judgment sabotage performance, and how focusing on effort instead of outcomes can dramatically improve results. In this episode, you’ll learn: • Why confidence comes from preparation and belief• The real reason people choke under pressure• How self-talk impacts performance• Why worrying about what others think kills confidence• How athletes train their minds to perform at their best If you want to perform better under pressure, whether in sports, business, or leadership, this episode is for you. Subscribe for more conversations on leadership, mindset, and building better teams. Scott Papek's Resources: https://www.maxoutmindset.com/ Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 418#0418 – If You Only Hear Good News, You’re Failing as a Leader with Phillip Wilson
If you’re a leader and you only hear good news, you may have a bigger problem than you think. In this episode of the Deep Leadership podcast, I sit down with Phillip Wilson, CEO of LRI Consulting Services and author of The Leader-Shift Playbook, to talk about one of the most overlooked leadership blind spots: power distance. Why don’t employees speak up?Why do teams hide mistakes?Why does bad news travel slowly… or not at all? We unpack the concept of approachability, the hidden cost of wide power distance, and what Phil calls the “hero assumption” — the mindset shift that transforms how leaders see their people. If you want more honest feedback, stronger trust, and a team that tells you the truth before problems explode, this conversation is for you. Phillip Wilson's resources: https://www.linkedin.com/in/pbwilson/ https://yourleadershift.com/ https://amzn.to/4rAXDEq Subscribe for more conversations focused on building a world with better bosses. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 417#0417 – When the Mission Fails: 5 Timeless Values Every Leader Must Live with Andy Crocker
What do you do when the mission fails? In this episode of Deep Leadership, I sit down with aerospace executive Andy Crocker to talk about what happens when a career-defining project collapses. After competing against SpaceX and Blue Origin for NASA’s Human Landing System, Andy and his team lost the contract — not once, but twice. For many leaders, that kind of loss can shake your identity. Instead of walking away bitter, Andy stepped back and asked a harder question: Who am I without the mission? That reflection led him to write The Unconditionals, a book built around five timeless values every leader must live: Love (yes, even in high-performance environments) Gratitude Integrity Accountability Endeavor We talk about why values aren’t “soft skills,” how trust is built and rebuilt, what accountability really means, and why humanity is more important than ever in the age of AI. If you’ve ever faced failure, questioned your leadership, or wondered what truly holds high-performing teams together, this conversation is for you. Leadership is a people business. And when everything falls apart, values are what keep you standing. 🎯 Get Andy’s book: https://andycrockerbooks.com/ 🎙 Subscribe for more conversations with top leaders 🔔 Share this episode to help us build a world with better bosses Until next time — lead well. Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 416#0416 – The Hidden Reason High Achievers Struggle in Marriage with Gabriela Embon
Are you winning at work but quietly struggling at home? In this episode of Deep Leadership, I sit down with Gabriela Embon, author of Becoming a Power Couple, to talk about why high achievers often succeed in their careers but fail to invest in the most important partnership of their lives. We discuss: Why work-life balance is a myth for driven leaders The difference between balance and integration How to think of your marriage as a co-founded enterprise The 4 Pillars that build resilient, high-performance relationships Why your relationship is the infrastructure behind your leadership If you’re a founder, executive, entrepreneur, or ambitious professional, this conversation will challenge how you think about success. Because leadership doesn’t start at the office. It starts at home. Your marriage should be an asset, not a liability. Listen in and learn how to build a power couple that multiplies impact instead of dividing energy. Subscribe for more conversations that help you build a world with better bosses. Learn more from Gabriela Embon here: https://gabrielaembon.com/ https://amzn.to/4tA6ZBP https://gabrielaembon.com/prologue-becoming-a-power-couple/ Subscribe for more powerful leadership conversations! Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 415#0415 – Real Leadership Isn’t Learned in a Classroom with Chris Hossfeld
Most leadership training happens in classrooms.Real leadership doesn’t. In this episode, I’m joined by Chris Hossfeld, a 27-year U.S. Army veteran and founder of Barrel Strength Leadership, who develops leaders by taking them to historic battlefields like Gettysburg and Normandy. We explore why pressure, emotion, and shared experience shape leaders far more than PowerPoint slides ever can. Chris explains how high-stakes environments force clarity, build trust, and reveal what leaders are truly made of—and how those lessons translate directly to business, manufacturing, and executive teams. If you believe leadership is forged in real moments, not theoretical ones, this conversation is for you. Learn more from Chris Hossfeld here: https://www.linkedin.com/company/barrel-strength-leadership/ https://www.barrelstrengthleadership.org/ Subscribe for more powerful leadership conversations! Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 414#0414 – How Pressure Turns Good Leaders Into Bad Bosses with Sabina Nawaz
How Pressure Turns Good Leaders Into Bad Bosses Most leaders don’t fail because they lack skill or good intentions. They fail because pressure changes how they show up. In this episode, executive coach Sabina Nawaz explains why pressure, not power, is the real force that corrupts leadership. Drawing from her work with senior leaders at Microsoft and Fortune 500 companies, Sabina breaks down how well-meaning managers slip into micromanaging, rescuing, and control—and how those habits quietly damage trust, performance, and culture. You’ll learn: Why pressure triggers the worst leadership behaviors The “sole provider” trap many leaders fall into without realizing it Why promotions are one of the riskiest moments in a leadership career How to lead yourself first so pressure doesn’t lead for you If you want to stay effective, human, and trusted as a leader—especially under pressure—this conversation is a must-listen. Learn more from Sabina Nawaz here: https://sabinanawaz.com/ https://growthroughpressure.substack.com/ Subscribe for more powerful leadership conversations! Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 413#0413 – Flexible Leadership: Why Rigid Leaders Fail in an Uncertain World with Kevin Eikenberry
Flexible Leadership: Why Rigid Leaders Fail in an Uncertain World The world has changed. Leadership has to change with it. In this episode, I’m joined by Kevin Eikenberry, one of the most influential leadership thinkers today and author of Flexible Leadership: Navigate Uncertainty and Lead with Confidence. We unpack why the leadership approaches that worked in the past often break down in today’s complex, fast-moving environment. Kevin explains why great leaders must stay consistent in values but flexible in how they lead, and why treating every challenge as a crisis leads to bad decisions. We dive into real-world examples, including when command-and-control leadership works, when it fails, and how context should drive your leadership approach. We also explore: Why “leadership style” can become a trap The difference between complicated, complex, and chaotic situations How flexible leaders improve their odds without losing trust Why mindset matters more than tools or techniques How habits, not intentions, determine leadership effectiveness If you’re leading people through uncertainty, change, or growth, this conversation will challenge how you think about leadership and give you a better way forward. 📘 Learn more about Kevin’s book Flexible Leadership - https://amzn.to/4a8mOI9 🎁 Free chapter and resources available - https://kevineikenberry.com/flexible-leadership/ Subscribe for more powerful leadership conversations! Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices
Ep 412#0412 – The Hidden Emotional Cost of Change Every Leader Overlooks with John Fisher
Most change initiatives fail for one reason: leaders ignore the emotional impact of change. In this episode, I’m joined by John Fisher, creator of the Fisher Change Curve, to explain what employees actually experience during change—and what leaders must do to guide people through it. We cover: Why change feels like loss The emotional stages of change at work Why resistance happens and how to reduce it Practical ways leaders can lead change without breaking trust If you’re leading organizational change, managing resistance, or navigating constant disruption, this conversation will reshape how you think about change management. Change isn’t just operational.It’s personal. Connect with John: John Fisher's website - https://c2d.co.uk/ John Fisher on LinkedIn - https://www.linkedin.com/in/c2dlimited/ Sponsors: Cadre of Men Farrow Skin Care Salty Sailor Coffee Company Leader Connect The Qualified Leadership Series ____ Get all of Jon Rennie's bestselling leadership books for 15% off the regular price today! HERE Learn more about your ad choices. Visit megaphone.fm/adchoices