In this episode, Jon breaks down what it means to be the “doctor” of the organization you’ve inherited. ReLeading is less like raising a child and more like adopting an adult with pre-existing conditions, and the first step is always a diagnosis.

Jon walks through five health metaphors—cardiovascular health, high blood pressure, arthritis, diabetes, and obesity—to show how hidden issues in culture, pace, conflict, systems, and overload can keep an organization unhealthy.

You’ll learn what symptoms to look for, how to treat them, and how to lead your team back to health from the inside out.

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In this episode, Jon shares four moments in leadership that almost took him out. He opens up about battling self-doubt, carrying the pressure of expectations, leading without enough resources, and realizing that a mindset of lack had slowly taken over.

Now eleven years into his role, Jon reflects on what nearly broke him, how he got through it, and why he’s still leading today. If you’ve ever felt the weight of leading something you didn’t start, this conversation will hit home.

Jon would love to hear what challenges you’re facing right now as a leader. Leave a comment wherever you’re listening.

Instinct got you through the wilderness, but it won’t get you into the Promised Land. In this episode, Jon Chasteen unpacks the critical shift every ReLeader must make: from leading by instinct to leading with intention.

Jon shares his personal wake-up call, realizing that frustration with systems, staff, or culture often pointed back to his own leadership failures.

Drawing from Joshua’s transition moment (“When the manna stopped, Israel didn’t panic; they planted”), he explores what it looks like to stop reacting to yesterday’s problems and start designing tomorrow’s future.

Through three practical shifts, Jon shows how ReLeaders can move from survival to strategy:

1. Stop Managing Around People — Start Leading Through Culture

2. Stop Doing It All — Start Developing Others

3. Stop Avoiding Hard Conversations — Start Restoring Healthy Accountability

Whether you’re inheriting a ministry, rebuilding after a crisis, or simply ready to grow beyond maintenance mode, this episode will help you trade instinctual reactions for intentional rhythms that build a healthy, lasting culture.

Most leaders are wired to start things. But what if the most powerful thing you could do as a leader isn’t to start something new — it’s to stop something old?

In this episode, Jon Chasteen unpacks The Power to Stop — a countercultural principle that every ReLeader eventually has to learn. Using Michelangelo’s sculpture of David as a metaphor, Jon explores how greatness is often revealed not by what we add, but by what we remove. Just like a sculptor chips away what doesn’t belong, effective leaders must learn to prune, pause, and say no — not out of weakness, but out of wisdom.

Through Scripture and stories, Jon walks through four truths every ReLeader needs to understand:
1️⃣ Pruning Isn’t Punishment; It’s Preparation — God cuts back fruitful branches so they can produce even more.
2️⃣ Stopping Isn’t Quitting; It’s Trusting — Like Moses learning from Jethro, wise leaders know when to let go and share the load.
3️⃣ Saying No Isn’t Weakness; It’s Wisdom — Boundaries create margin, and margin fuels mission.
4️⃣ Less Isn’t Loss; It’s Leverage — Jesus wasn’t afraid of smaller crowds because He knew focus multiplies fruit.

Every ReLeader faces the same internal questions: Who am I to lead this? Do I have what it takes? What if I’m not enough? In this episode, Jon Chasteen unpacks the calling of Moses in Exodus 3 and shows how God answers those very questions—not by listing tasks, but by affirming identity, revealing capacity, and supplying sufficiency. If you’re leading something you didn’t start, this episode will remind you: God chose you, equipped you, and will fill in every gap if you're willing to go. Whether you’re leading a church, a team, or a turnaround, this is the reminder you didn’t know you needed.

Ever felt overwhelmed stepping into a new leadership role? You're not alone! Join Jon Chasteen as he talks with Ben Kendrew, Lead Pastor at Arise Church in New Zealand, about finding confidence amidst uncertainty. Ben shares practical insights on navigating leadership challenges, overcoming imposter syndrome, and remaining authentic even in tough times. Discover how difficult seasons are often God’s preparation for something greater. Don’t miss this inspiring conversation! 🌊💡 #Leadership #Confidence #Authenticity

In this episode, Jon Chasteen unpacks the often misunderstood concept of meekness in leadership. 🤔 Drawing from the words of Jesus about John the Baptist and the disciples, he explores how true strength is found in restraint and service—not in overpowering others. 💪 With insights for business leaders, pastors, and even dads, Jon challenges us to rethink what it means to lead with authority and kindness. Is it possible to be both strong and meek? 🤯 Tune in to find out how embracing a quiet strength could transform your leadership!#LeadershipHacks #ServantLeadership #QuietStrength #MeekNotWeak #FaithAndLeadership #ReLeader #PowerUnderControlWhat do you think? 🎧🔥

Nobody likes to wait—but what if your waiting season is actually preparing you for something greater? In this message, Jon Chasteen unpacks the hidden power of patience, revealing how it’s not just a virtue, but a Godly gain. Discover why the biggest callings often require the longest waits, and how God uses patience to build your strength, increase your capacity, and prepare you for takeoff. If you’ve ever felt stuck, this message is for you! Watch now and learn why it’s better to be patient than powerful. 🚀🔥 #Patience #GodsTiming #SpiritualGrowth

In this episode, I open up about a recent, deep stirring I’ve felt to ReLead in a place where I’ve already been leading for 10 years. It’s a vulnerable moment for me because, after so much time in the same role, you get comfortable with the way things are. But sometimes, God begins to nudge us, pushing us to shake things up and disrupt the norms we've grown used to. What does it really feel like when that urge comes? When we sense it's time to step out of our routine and re-lead from within? We’ll dive into the emotions, the discomfort, and the excitement that come when you realize it’s time to chart a new course, even in familiar territory.

In this episode, Jon introduces his fresh, unfiltered podcast format—ditching the polished production for a raw, personal approach. Dive in as he explores a crucial question: Who is really king in your organization? Plus, discover the three pitfalls that every leader crowned as "king" is bound to stumble over. Don’t miss this candid conversation that’s as real as it gets!