787: Better Leadership Through Humor, with Chris Duffy

Leadership isn't just about strategy and structure—it's also about presence, connection, and the quiet power of humor. In this episode, Chris Duffy, author of *Humor Me*, challenges the idea that humor is just about telling jokes or being the center of attention. Instead, he reframes it as a radical act of generosity: noticing the absurd, embracing imperfection, and creating space for joy in the mundane. Drawing from his experience as a teacher and comedian, Duffy reveals how a simple shift—like laughing at a coffee stain or a typo on a client gift—can build trust, reduce fear, and make teams more creative and resilient. He argues that humor isn't a distraction from leadership; it’s the very tool that makes leadership more human, more effective, and more joyful. The episode dismantles the myth that leaders must be flawless, showing how selective vulnerability—acknowledging failure with laughter—actually strengthens influence and connection. The conversation unfolds through practical, actionable insights: the 'new bathroom mindset' for retraining attention, the power of asking second questions to uncover hidden truths, and the radical idea of celebrating failure as a path to excellence. From a LinkedIn prank that got him banned to a museum of bad art that transforms how we see beauty, Duffy shows that humor is not performance—it’s perception. By training ourselves to notice the strange, the awkward, and the absurd, we don’t just laugh more—we lead better.