Three hundred episodes.
For this milestone edition of Leaning Into Leadership, I wanted to do something different. Instead of looking back by myself, I invited six incredible leaders—and people who have become an important part of my own journey—to join me for a conversation about leadership, growth, relationships, and the people who help us become better versions of ourselves.
Joining me for Episode 300 are Jason Ryan, Katie Kinder, Todd Bloomer, Bentli Lewis, Josh Tovar, and Brandon Beck. Every one of them has appeared on the podcast before. More importantly, every one of them has challenged me, encouraged me, taught me something, and sharpened the iron along the way.
We start with a simple question: What are you learning about yourself as a leader right now?
That opens the door to a powerful conversation about moving from solving problems to developing people, learning to lead through influence, building leadership capacity in others, staying close to the work, adapting when circumstances change, and recognizing that leadership is always a long game.
We also dig into how leaders continue to sharpen the iron. The answers range from surrounding yourself with people who challenge your thinking and intentionally building your network, to reading, listening, taking care of yourself, prioritizing family, staying curious, seeking feedback, and remaining humble enough to recognize that what worked yesterday may not work tomorrow.
Then we turn the tables and look back at Leaning Into Leadership itself. Each guest shares an episode or conversation that has stayed with them—and hearing what they chose reminded me why I started this podcast in the first place.
What began as an opportunity to grow a platform has become something much more meaningful: a place for me to learn alongside some remarkable people.
We close with a lightning round built around three questions every leader should consider:
That final question may be the most important one of the entire episode.
Leadership rarely happens alone. Somewhere along the way, someone sees something in us. They encourage us. Challenge us. Open a door. Invite us to the table. Sometimes they see our potential before we do.
Episode 300 is a celebration, but it is also a reminder of what leadership is really about: people, relationships, growth, and creating opportunities for others to become more than they thought possible.
To every guest who has joined me over these first 300 episodes and every listener who has spent part of their week with Leaning Into Leadership—thank you.
300 down. We’ve got way more than 300 to go.
This Episode Is Sponsored by HeyTutor
HeyTutor partners with schools and districts to provide high-impact, in-person tutoring in literacy and math, giving students targeted support alongside the work of classroom teachers.
Learn more about how HeyTutor can support student learning in your school or district at HeyTutor.com