For leaders, there’s no avoiding failure; it just comes with the territory. However, how leaders respond when things don’t go as planned—how they lead through failure—is absolutely critical. This month, we are going to focus on ways that leaders can lead through failure and turn potential disappointment into powerful lessons for growth and renewal. In this episode, GLN President and CEO, David Ashcraft, shares stories of times when things did not go as planned, and how he has learned to “fail well” over time.
SUMMARY
For leaders, there’s no avoiding failure; it just comes with the territory. However, how leaders respond when things don’t go as planned—how they lead through failure—is absolutely critical. This month, we are going to focus on ways that leaders can lead through failure and turn potential disappointment into powerful lessons for growth and renewal. In this episode, GLN President and CEO, David Ashcraft, shares stories of times when things did not go as planned, and how he has learned to “fail well” over time.
IN THIS EPISODE:
- When is a time that David had a project or idea that he was passionate about, but that did not turn out the way he wanted?
- How can you move through discouragement over the results to a posture of learning?
- Does David see himself as a perfectionist?
- How can you build a culture of candor in a team?
- If you tend to be a people pleaser, what can you do to start receiving feedback more productively?
- If you’re going to experiment, be aware of how bad the consequences could be, and calculate accordingly.
LISTEN
Apple Podcasts | Spotify | YouTube
STANDOUTS AND TAKEAWAYS
- Perspective is very important to determine whether or not something is actually a failure.
- Try new things but try them wisely.
- The desire for success can help mitigate the desire to please others.
- Address shortcomings and “gaps” with truth and grace, not suspicion or doubt.
- “Failure is not the enemy, inaction is” (Carrie Lohrenz).
LINKS MENTIONED
- Website: Leader365 and Team365
- Website: Global Leadership Summit 2025
- Website: Global Leadership Network
Related
Ep 211: On Calling, Counsel and Courageous No's
In this episode of the Global Leadership Podcast, GLN President and CEO David Ashcraft talks with Priscilla Shirer about how leaders discern what is truly theirs to carry. Priscilla shares practical wisdom on calling, wise counsel, humility, accountability, and learning to say yes or no from a place of clarity rather than fear or guilt.
Ep 209: Communication, Candor and Trust
In this episode, Whitney Putnam and GLN President and CEO David Ashcraft talk about one of the most common leadership challenges: how to communicate with clarity, candor and care when the stakes are high. They unpack a real moment from a recent GLN all-staff meeting, where a public challenge created tension, required follow-up and ultimately helped sharpen strategy. Whitney and David explore why leaders often think they are being clear when others are hearing something different, how trust makes hard conversations possible, and why “keeping short accounts” can prevent tension from becoming toxic.
Ep 208: Leading When the Plan Falls Apart with Craig Groeschel
In this episode, David Ashcraft talks with Craig Groeschel, founder and senior pastor of Life.Church, about how leaders can respond when leadership does not go as planned. Craig reflects on failed ideas, organizational pivots, team conflict, and the ongoing discipline of letting go as leadership expands. He also shares how humility, preparation, prayerfulness, candor and trust have shaped the way he leads through uncertainty.
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.

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