The Surthrivalist Podcast with Zach Wise

Let Them Learn: A Coaching Conversation on Leading Through Mistakes with Ryan Calistro | Ep. 1

Have you ever watched someone on your team walking straight toward a mistake… and wrestled with whether to step in or let them learn the hard way?
That’s exactly where today’s guest, Ryan Calistro, finds himself—leading a 200+ person, multi-brand organization and learning how to lead without rescuing.
In this coaching conversation, Zach and Ryan dig into the tension between being a high-driving, answers-oriented leader and becoming the kind of leader who multiplies others by asking better questions. Along the way, they talk candidly about ego, fear of failure, and what it really costs to let your team experience non-fatal consequences for the sake of long-term growth.
In this real-time coaching conversation, we talk through:
How to resist the urge to rescue and instead lead your team through non-fatal failures
Using purposeful questions to create clarity, buy time, and help others discover their own solutions
Turning stressful leadership moments into growth opportunities through reflective coaching
Navigating the humility, maturity, and patience required to lead a large organization without micromanaging
 
Resources Mentioned:
Books:
Multipliers: How the Best Leaders Make Everyone Smarter by Liz Wiseman: https://amzn.to/4akBRPk
The Coaching Habit: Say Less, Ask More & Change the Way You Lead Forever by Michael Bungay Stanier: https://amzn.to/4rmB1I5
Schedule a free 15-minute chat with Zach - https://calendly.com/surthrival/chat-with-zach
Apply to be coached on The Surthrivalist Podcast - https://smallbizsurthrival.com/podcast
 
Connect with The Surthrivalist:
Website: https://smallbizsurthrival.com
Facebook: https://www.facebook.com/smallbizsurthrival
LinkedIn: https://www.linkedin.com/in/zjwise
YouTube: https://www.youtube.com/@smallbizsurthrival

Welcome to The Surthrivalist: Real Coaching for Real Builders

The Surthrivalist Podcast is where Christian entrepreneurs get the real, unscripted coaching they’ve been craving. Hosted by Zach Wise, this show tackles the tension between building a business that matters and becoming the man God has called you to be. Expect raw conversations, honest struggles, biblical wisdom, and practical strategy to help you move from surviving to surthriving—in business, in family, and in faith.
Resources:
Schedule a free 15-minute chat with Zach - https://calendly.com/surthrival/chat-with-zach
Apply to be coached on The Surthrivalist Podcast - https://smallbizsurthrival.com/podcast
Connect with The Surthrivalist:
Website: https://smallbizsurthrival.com
Facebook: https://www.facebook.com/smallbizsurthrival
LinkedIn: https://www.linkedin.com/in/zjwise
YouTube: https://www.youtube.com/@smallbizsurthrival