Trust Falls and Reality Checks: The Uncomfortable Truth About Leadership Retreats with Jeff Conroy
No More Leadership BS
Trust Falls and Reality Checks: The Uncomfortable Truth About Leadership Retreats with Jeff Conroy
October 29, 2025
The Retreat Myth: Why Your Leadership Summit Won't Fix Your Broken Board (But It Could Start Something) Think booking a fancy retreat will magically fix your dysfunctional board or fractured team? Spoiler alert: It won't. But before you cancel that reservation, hear us out. In this no-holds-barred episode, the Leadership BS crew tackles one of the biggest misconceptions in organizational management: the idea that retreats are the ultimate cure-all for leadership problems. Why Leaders Keep Getting This Wrong Most leaders treat retreats like corporate fairy dust—go offsite, add a trust fall, throw in a nice dinner, and poof! Problems disappear. Except they don't. You can't run away from your culture because you bring it with you. The panel breaks down why "retreat" is actually the wrong word (you're literally running away from something), why trust falls won't build actual trust, and how unstated expectations doom your event before it starts. If you don't have clarity on your "why," you're basically throwing an expensive party where nobody knows the point. The Real Problem Isn't Your Board—It's Your Leadership Here's the uncomfortable truth: If your board is broken, your leadership is the common denominator. Everything rises and falls on leadership, and no amount of icebreakers will change a toxic culture if the person at the top won't look in the mirror first. The crew discusses why making people part of the story matters more than fancy venues, and how one genuine moment of leadership vulnerability can accomplish more than a dozen trust exercises. The Bottom Line A retreat—or better yet, a "leadership summit" or "advance"—isn't a destination. It's not the staircase; it's just one step. It can be the beginning of cultural change, but only if you approach it with crystal-clear expectations, genuine leadership accountability, and a focus on where you're going rather than where you've been. Tune in for: Why the word "retreat" is setting you up for failure from the start The one question everyone's asking that leaders ignore: "What's in it for me?" How to build trust (hint: it doesn't involve catching anyone) The single most important thing to accomplish if everything else fails Real talk about why your board or team dysfunction probably starts with you This episode is your reality check served with a side of actionable wisdom. Because sometimes the best leadership advice is admitting that throwing money at a problem in a hotel conference room isn't actually leadership—it's avoidance dressed up with catering.
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Today's Featured Coach - 
Jeff Conroy - Organizational and Non-profit Expert, Motivational Speaker, Coach -  Executive Leader | Difference Maker for nonprofits in strategic planning, operations, and fundraising and development. Owner/Founder of Conroy Leadership Consulting, LLC. Reach Jeff at [email protected] or  208-215-6285

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