Deep Leadership
“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!
Episodes
May 2, 2026 • 40 mins
Why do smart people get things so wrong?
In this episode of Deep Leadership, I sit down with Professor Peter Lamont to explore a powerful idea: it’s not what you think that matters most—it’s how you think.
We dive into his concept of Radical Thinking—a different approach to critical thinking that challenges you to examine the roots of your beliefs. Peter explains why every one of us is operating from a limited view of reality, sh...
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April 30, 2026 • 35 mins
Why Self-Awareness Is the Leadership Skill Most Leaders Lack
Most leaders don’t fail because they lack skill, experience, or good intentions—they fail because they don’t truly understand themselves.
In this episode of Deep Leadership, I sit down with Margaret Andrews, author of Manage Yourself to Lead Others, to unpack why self-awareness is the foundation of effective leadership—and why so many leaders struggle without it.
We ta...
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April 25, 2026 • 36 mins
Leadership Decisions You Can’t Afford to Get Wrong
In this episode of Deep Leadership, I sit down with Dr. Linda Henman, advisor, author, and expert in high-stakes decision-making, to talk about the leadership decisions you simply can’t afford to get wrong.
Most organizations are full of people who know how to execute. They run fast, deliver results, and get promoted. But when the stakes are high, execution isn’t enough. The rea...
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April 22, 2026 • 39 mins
Most leaders don’t fail because they don’t care.
They fail because no one ever taught them how to lead.
In this episode of Deep Leadership, I sit down with Robert Heath Sr., a former Marine Corps officer, attorney, and leadership coach, to unpack one of the biggest traps leaders fall into—the need to be the fixer.
If you’re the person everyone relies on to solve problems, this conversation might hit close to home.
Because the ...
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April 18, 2026 • 37 mins
What happens when your best performer becomes your worst leader?
In this episode of Deep Leadership, I sit down with Dr. Peter James, President and CEO of HCG Strategic Partners, to unpack one of the most common (and costly) mistakes organizations make: promoting great individual contributors into leadership roles without preparing them to lead.
Peter brings a rare perspective shaped by leadership in the military, corporate Ameri...
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April 11, 2026 • 40 mins
Broken Trust: How Great Leaders Fix It
Trust is at some of the lowest levels we’ve ever seen—and leaders are paying the price.
In this episode, I sit down with Dr. Darryl Stickel to unpack what trust really is, why it’s collapsing in today’s uncertain world, and how great leaders rebuild it inside their teams.
We talk about the real definition of trust (it’s not what you think), why confidence without certainty destroys credibil...
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April 5, 2026 • 37 mins
What if you didn’t wait for permission… and just claimed authority?
In this episode of the Deep Leadership podcast, I sit down with Tom Kubiniec, President and CEO of Securit Tactical, who built multiple successful companies without a degree, corporate experience, or a traditional playbook.
Tom shares how he carved out a leadership position in an industry that had no clear expert—and why sometimes the fastest way forward is to st...
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March 27, 2026 • 36 mins
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 communic...
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March 21, 2026 • 38 mins
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 scal...
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March 14, 2026 • 35 mins
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, hu...
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March 7, 2026 • 32 mins
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 bui...
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February 28, 2026 • 38 mins
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?
W...
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February 22, 2026 • 35 mins
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 st...
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February 13, 2026 • 37 mins
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 o...
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February 7, 2026 • 39 mins
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 environme...
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January 31, 2026 • 37 mins
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 mic...
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January 24, 2026 • 34 mins
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....
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January 17, 2026 • 38 mins
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
Pract...
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January 10, 2026 • 41 mins
How Great Leaders Turn Empathy into Power
Empathy is praised in leadership—and often quietly punished.
In this episode, Jon Rennie is joined by Jess Baker, chartered business psychologist and author of The Super Helper Syndrome, to explore how great leaders turn empathy into real power without being overlooked or burned out.
Jess explains why highly empathic professionals are often passed over for leadership roles, even though t...
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January 3, 2026 • 37 mins
Brave Leadership: How Courage, Not Comfort, Drives Results with Jill Schulman
Fear shows up quietly in leadership.
It delays decisions. Avoids hard conversations. Keeps talented people playing it safe.
In this episode of Deep Leadership, I’m joined by Jill Schulman, Marine Corps veteran, leadership consultant, and author of The Bravery Effect, to break down why courage—not comfort—is what actually drives results.
Jill shares ...
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