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 202: Creating Meaningful Change Through Faith and Entrepreneurship (with Justin Forman)
Leadership isn’t just about building something successful; it’s about building something meaningful, aligning what you believe with how you lead and using what you’ve been given to make a difference. Today’s guest is someone who has spent years helping leaders do exactly that.
Ep 201: Five Essential Functions of Leadership (with Henry Cloud)
Our President and CEO, David Ashcraft, recently sat down with Dr. Cloud for a conversation about his upcoming book Your Desired Future. This book is basically a masterclass in how to lead—yourself and other people and is exactly what we’ve come to expect from Henry: deep psychological insight with super practical application.
Ep 200: Resilience for Leaders (with David Ashcraft)
Today we're talking with GLN president and CEO David Ashcraft about resilience. This conversation will help you think about why resilience is necessary and the importance of celebrating small wins. With the right inputs, we can be resilient leaders.
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.
