Mastering Leadership Challenges with Ryan Leak ๐
Join us on The Servant Leadership Podcast as Ryan Leak shares proven strategies for overcoming failure and leading difficult people effectively. Discover insights from a best-selling author and leadership expert!

Servant Leadership Podcast
69.2K views โข Apr 8, 2025

About this video
Today on The Servant Leadership Podcast, we welcome Ryan Leakโa best-selling author, leadership coach, and sought-after speaker. Ryan is a leading voice on risk-taking, growth, and leadership transformation. He challenges leaders to step outside their comfort zones and embrace failure in order to thrive. His book Chasing Failure reveals how the greatest leaders take risks and use failure as fuel to achieve their biggest goals. Instead of seeing failure as something to avoid, Ryan shows how it can be the key to innovation and lasting success. His latest book How to Work With Complicated People equips leaders to navigate the everyday challenges of working with others, In this episode, Ryan shares powerful insights on unlocking potentialโboth in yourself and in those you lead. If youโre leading at any level, this conversation will challenge the way you think about failure, success, and the impact you can make.
Timestamps:
00:00 Ryan Leak's Intro
00:57 Welcome Ryan Leak
01:11 Ryan's Journey to Become a "Speaker-Preneur"
02:58 Speaking to Corporate Boards vs. Church Leadership
05:20 Background on "Chasing Failure"
09:06 Advice For Others About Chasing Their Dreams
11:26 Learning From Your Failures
12:21 Does It Get Easier Over Time?
16:16 New Book - "How To Work With Complicated People"
19:15 Servant Leadership Perspective
22:16 The Hardest Part About Leadership
25:09 Building an "Open To Fail" Culture
29:30 Behind The Scenes Work - Complicated People
35:42 10-Rapid-Fire Questions
41:04 Closing
Want to learn more about Ryan Leak? Check out his website below:
https://www.ryanleak.com/
Servant Leadership:
URL:ย https://servantleadershippodcast.org/
Facebook:ย https://www.facebook.com/ServantLeadershipPodcast
Instagram:ย https://www.instagram.com/servantleadershippodcast
LinkedIn: https://www.linkedin.com/company/servant-leadership-podcast/
X (Twitter): https://x.com/servant_podcast
Timestamps:
00:00 Ryan Leak's Intro
00:57 Welcome Ryan Leak
01:11 Ryan's Journey to Become a "Speaker-Preneur"
02:58 Speaking to Corporate Boards vs. Church Leadership
05:20 Background on "Chasing Failure"
09:06 Advice For Others About Chasing Their Dreams
11:26 Learning From Your Failures
12:21 Does It Get Easier Over Time?
16:16 New Book - "How To Work With Complicated People"
19:15 Servant Leadership Perspective
22:16 The Hardest Part About Leadership
25:09 Building an "Open To Fail" Culture
29:30 Behind The Scenes Work - Complicated People
35:42 10-Rapid-Fire Questions
41:04 Closing
Want to learn more about Ryan Leak? Check out his website below:
https://www.ryanleak.com/
Servant Leadership:
URL:ย https://servantleadershippodcast.org/
Facebook:ย https://www.facebook.com/ServantLeadershipPodcast
Instagram:ย https://www.instagram.com/servantleadershippodcast
LinkedIn: https://www.linkedin.com/company/servant-leadership-podcast/
X (Twitter): https://x.com/servant_podcast
Video Information
Views
69.2K
Likes
18
Duration
41:37
Published
Apr 8, 2025
User Reviews
3.9
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