How do you react when you fail? Have you ever wished that you could learn more quickly from your failures and move on? In this episode, GLS Executive Producer Lori Hermann sits down with CEO, executive coach and best-selling author Ryan Leak to hear how he learned more from his failures than he ever did from his successes. In their conversation, they discuss his documentary, “Chasing Failure,” and how failure became the best teacher throughout his life.
IN THIS EPISODE
- What was the story behind Ryan’s documentary, “Chasing Failure”?
- How was the experience of chasing failure different from planning the documentary?
- How did he end up working with the Dallas Mavericks?
- What does Ryan really like to teach on?
- What legacy would Ryan like to leave?
- From his perspective, what is the biggest challenge that leaders are currently facing?
- Overall, what has chasing failure taught Ryan?
LISTEN
Apple Podcasts | Spotify | YouTube
STANDOUTS AND TAKEAWAYS
- Failures can help people more than any kind of success.
- People admire perfection from a distance, but they cannot relate to it, so it’s important for leaders to reveal what’s behind the scenes.
- Getting things wrong is just a part of the journey, so keep putting yourself out there: keep posting, keep, leading, keep trying new things.
- If you make what you’re doing always about others, it takes the pressure off.
- It’s difficult to lead effectively, and to keep growing, when your marriage isn’t well.
- Ask every person that serves you, “Is there anything going on in your life that I could pray for?”
- Don’t take change personally. Everyone is going through it.
- Though leading through change is difficult, it’s actually more challenging to follow through change. Leaders can help their organizations by being empathetic to what “front-line” employees are going through as change happens.
- Organizations respond positively when they believe that their strategic leaders are available to them.
- During seasons of change, try to not make decisions in a vacuum.
- As a leader, cultivate trust through an atmosphere of caring. Then, even if someone does not agree with a decision, they are more likely to support the decision.
LINKS MENTIONED
- Website: Ryan’s Website
- Website: “Chasing Failure” (YouTube)
- Website: Team365
- Website: Global Leadership Summit 2025
- Website: Global Leadership Network
FOLLOW US
Instagram | Facebook | LinkedIn | X |
SPONSOR
- This episode is sponsored by ECFA Leadership Standard.
Related
Ep 196: A Lifetime of Leadership (with John C. Maxwell)
Have you ever wished you could sit down with someone who has truly mastered their craft? Michael Jordan on winning; Mozart on music; Leonardo da Vinci on creativity. Not just to review their highlight reels but to unpack all the lessons they learned across their lives? Well, that’s what today’s conversation feels like because today we get to listen to John C Maxwell talk about leadership.
Ep 195: On Purpose and Calling (with David Ashcraft)
As a leader who is rolling into a new year, you might be thinking about what’s next. This conversation with GLN President and CEO David Ashcraft will encourage you with the unique ways you’ve been called to lead and center you by reminding you what it’s all about.
Ep 194: A Look Back at 2025 (with Whitney Putnam and Eric Case)
As 2025 wraps up and 2026 gets started, we thought we’d take a look back on all the great conversations we’ve had over the past year and pick a few of our favorites to share with you.
Leadership That Lasts
Team365 isn’t just a platform. It’s a commitment to grow, lead and live with purpose — every single day. Whether you’re here for content, community or clarity, you’re in the right place. Your leadership matters. Let’s keep going.
