Episode
Episode 300: Leadership Lessons From the People Who Helped Shape the Journey
- Podcast
- Leaning into Leadership
- Published
- Sep 23, 2026
- Duration seconds
- 4162
- Processing state
not_requested
Actions
POST https://stenobird.com/v1/public/podcasts/leaning-into-leadership-4658926/episodes/episode-300-leadership-lessons-from-the-people-who-helped-shape-the-journey/transcription-requests
Idempotently request low-priority transcript generation for this episode.GET https://stenobird.com/podcast/leaning-into-leadership-4658926/episode-300-leadership-lessons-from-the-people-who-helped-shape-the-journey.md
Read the agent-friendly Markdown representation of this episode resource.
Summary
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 alo…