The Leadership Skill You’re Underestimating: Humor

Two clients. Related feedback. Different directions.

Beth: "I want to see your sense of humor. It would soften the intensity and intimidation."

Brad: "People shut down when you're sarcastic. It creates distance."

Beth admires her CEO — someone who cuts tension with a sharp observation, disarms with self-deprecation, lands a point with an unexpected metaphor. She recognized that her serious, hyper-focused demeanor was stoking disconnection, not authority.

Brad saw something harder. His sarcasm has always been protection — a way to deflect when things get uncomfortable. He recognized it for what it was: passive-aggression dressed as wit.

Same feedback. Opposite problems. Both worth paying attention to.

Executives who develop their humor become sharper communicators, stronger collaborators, and more trusted leaders.

So how do you develop it?

Look at great comedians. Their humor isn't jokes — it's strategic wit. Intelligent, purposeful, and nuanced.

Seinfeld. Fey. Carlin. Newhart.

Each one teaches something:

Observation
Razor-sharp, relatable insights delivered simply. 

Storytelling
Warmth, wit, and vulnerability woven together. 

Reframing
Quick, humorous takes on the unexpected. 

Self-Deprecation
Laughing openly at your own imperfections. 

Banter
Fast, friendly, light. 

Irony and Paradox
Naming the contradiction in the room.

Executive humor is adaptable, authentic, spontaneous, and deeply human. It laughs at flaws — never at people. It finds the absurdity in high-stakes situations without minimizing them.

Done well, humor unites teams around shared truth. It diffuses tension, invites candor, builds trust, and makes hard work more bearable. It also makes ideas stick.

How do you develop it?

Honestly — I'm not sure you can manufacture it. What I've noticed: the more present and relaxed I am, the more it surfaces naturally. It's not something to force. It's something to access.

And it's contagious. When I genuinely appreciate someone else's humor, mine shows up more easily.

What brings out yours?