Leading With A Laugh: Lessons From The Comedy Stage

Most marketing executives spend their off-hours analyzing campaigns, reviewing trend reports, or scrolling through competitor ads. I spend mine on stage at comedy clubs, telling jokes about being dim-witted.

My stand-up journey began with improv. I was an empty nester looking for something fun. I’d spent so long performing in rooms that didn’t look like comedy clubs—executive meetings, keynote stages, QBRs—all strategy, polish, and control. I wanted the opposite of that. Something unfiltered. Something human.

Improv helped me loosen up, say “yes and,” and stop trying to control the outcome. It reminded me how fun it is to play—like we did as kids. Kids don’t analyze or plan—they just react to what’s in front of them.

I pushed further, signing up for a stand-up class. I’ve performed sets on stages in Pennsylvania and New Jersey, plus one unforgettable night at Gotham Comedy Club in Manhattan.

I didn’t expect any of it to show up at work. But it did. As it turns out, comedy wasn’t just helping me laugh more—it was helping me lead better.

What Stand-Up Taught Me About Leadership

• Get to the point—fast. In comedy, you have seconds to hook the audience. If the punchline takes too long, you’ve lost them. The same goes for presentations. Clients, stakeholders and employees need clarity, not a 12-slide PowerPoint. Comedy sharpens your ability to cut the fluff and say what matters.

• Read the room. A good comic adjusts based on energy and response. So does a good leader. I once joined an HR town hall to deliver a message about the importance of internal communications. It was one of the first times I’d spoken live—I was used to writing, not speaking. I was nervous; worse, I could feel the energy drop two minutes in. I paused, smiled, and said, “Sorry—public speaking isn’t my first language.” That one line got more reaction than the entire opening. I scrapped the rest and shifted to Q&A. It was a turning point.

In comedy, you refine your set based on what lands and what doesn’t. You learn to let go of what isn’t working—even if you love the line. Leadership works the same way. You have to pay attention to your audience, adapt in real time, and be willing to rework your message so it actually resonates.

• Make the joke about you. I’ve found a unique way to connect with my audience by making fun of myself in my set. This self-deprecation isn’t about undermining myself but about building trust. In the business world, this approach can work wonders. Leaders who own their mistakes or laugh at themselves create a more relaxed and open environment. You don’t have to be the funniest person in the room, but you do have to be the most honest.

I work with women who have criminal records—many still incarcerated. They’re resilient and often harder on themselves than anyone else could ever be. And too often, they assume the people around them—especially leaders—are perfect. It levels the playing field when I tell a story about messing up or poke fun at myself. It reminds them we’re all human—and that their voice belongs, too.

• Be human first. Comedy, like leadership, doesn’t work if you’re pretending. Audiences—and teams—can always tell when you’re not being authentic. Stand-up has taught me the value of dropping the polish when I need to and saying what I actually mean. Leading in a way that’s real, not rehearsed, is what truly connects with people.

• Laughter builds culture, too.

While we often focus on KPIs, performance reviews, and optimization, we shouldn’t underestimate the power of laughter in the workplace. A team that can laugh together—really laugh—is a team that trusts each other. It’s a team that feels safe and is more willing to take creative risks because it is not afraid of falling flat now and then.

Humor isn’t fluff. It’s function. It breaks tension, connects, and reminds people: you’re allowed to be human here.

After one of my sets, a few friends came up to me and said, “But you’re not dimwitted!” They were trying to defend me—against my own jokes. I just laughed. I don’t think I’m dumb. I took stories from my childhood where I absolutely was dimwitted and heightened them. That’s the point. That’s the fun.

There’s something freeing about laughing at your own story. It shifts how you carry it. And it gives other people permission to do the same.

Marketing Is Performance—So Is Leadership

Both require timing, audience awareness, and the courage to say something real. Stand-up taught me that failure isn’t fatal—it’s feedback. And sometimes, the best thing you can do as a leader is to let people laugh, especially when the stakes are high.

I don’t think every executive needs to take up comedy. But we could all benefit from lightening up—from loosening our grip on being perfect, polished and always on.

Because the world doesn’t need another perfectly worded email.

It could use a good laugh, though.