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787: Better Leadership Through Humor, with Chris Duffy
Brief
Chris Duffy visited Coaching for Leaders (episode 787, June 15, 2026) to argue that humor is a learnable leadership tool that helps leaders be more present, creative, connected, and resilient. Host Dave Stachowiak began skeptical that humor would rank among top leadership competencies; Duffy reframed the debate by showing how humor shortcuts the hard work of building vulnerability and connection. Rather than performance or attention-seeking, Duffy defines a practical sense of humor as noticing the absurd, acknowledging imperfections, and laughing with people — not at them. He illustrated the point with a study-style example in which equally qualified job candidates who acknowledged a coffee stain were rated more favorably than immaculate candidates, demonstrating that candid imperfection boosts likability.
The conversation moved through several applied practices. Duffy offered the “new bathroom mindset” — act as if you’re encountering routine settings for the first time to strengthen observation skills and surface comic detail — and urged leaders to ask follow-up questions (Dave and Duffy both endorsed a simple 'ask a second question' tactic) to reveal unexpected material. He recommended deliberately “celebrating the bad”: normalizing flawed early work (he pointed to Boston’s Museum of Bad Art) so teams iterate without shame. Duffy also emphasized selective vulnerability: acknowledge problems honestly but in a way that sustains confidence and direction. He backed these ideas with personal anecdotes — a fifth-grade student named Gary whose humorous cafeteria reviews sparked engagement, and a LinkedIn prank in which Duffy listed himself as 'CEO of LinkedIn' for a year before being flagged — to show both the power and the necessary boundaries of workplace humor. Overall, Dave and Chris largely agreed: humor, practiced as generosity and attention, is a pragmatic leadership skill that can be cultivated and used to deepen connection, surface insight, and make organizational life more humane.
Why it matters
Episode 787 of Coaching for Leaders (host Dave Stachowiak) aired June 15, 2026 and featured Chris Duffy, author of Humor Me: How Laughing More Can Make You Present, Creative, Connected, and Happy.
Key details
- Chris Duffy told a replicated-study style anecdote: equally qualified job candidates who acknowledged a spilled coffee (i.e., visible imperfection) were rated more highly than their pristine counterparts — illustrating that self-deprecating honesty increases likability and hireability (Duffy).
- Duffy reframed humor as a leadership tool — not performance — that shortcuts other competencies (presence, vulnerability, connection) and makes difficult tasks feel like less 'homework' (Chris Duffy).
- Practical practice: Duffy’s 'new bathroom mindset' trains attention by treating routine spaces/events as if you’re seeing them for the first time (notice details like towels, soap, toilet paper orientation) to build the muscle of noticing and surface everyday absurdities to laugh about (Chris Duffy).
- Concrete tactical advice endorsed by Dave Stachowiak and Duffy: be present, ask a second/follow-up question to uncover unexpected, often funny details, and deliberately seek small weird facts to use as connective humor in everyday leadership interactions.
- Duffy recommends 'celebrating the bad' as a cultural practice: normalize and laugh at early, bad work (he cites the Museum of Bad Art) so teams feel safe iterating toward good ideas rather than hiding mistakes.