What We Can Learn About Great Storytelling from Comedians

Back in the 80s, I got to be in the audience for Top of the Pops. I thought it was going to be a wild, electric, party-like atmosphere—the kind you saw on TV. The reality? Less rock ‘n’ roll, more school trip with grouchy teachers. Instead of dancing and soaking up the music, we were shuffled from stage to stage by an unimpressed floor crew. 

Then came the weirdest moment. Chaka Khan was mid-performance when, out of nowhere, a bloke who looked alarmingly like Limahl (yes, Too Shy Limahl) appeared behind me. He prodded my should and hissed, “Dance, penis breath!”

Now, I danced—because what else do you do when an angry Limahl lookalike gives you an order? For years, I assumed “penis breath” was just a weird insult. It took me three decades to realize he was actually being homophobic.

Punchlines and the ‘Ohhh’ Moment 

That delayed realization? That’s exactly what makes a great joke work (ideally, not 30 years later). A punchline flips what you thought you knew and makes you see something differently. That’s exactly what great business storytelling does. A good story isn’t just a list of events—it delivers a twist, a moment where the audience goes, “Ohhh, now I get it.”

Why Most Business Stories Fall Flat

Here’s the problem: most business storytelling doesn’t have that moment. It’s just a dull series of facts. No twist, no surprise, no payoff. It’s like a comedian dragging out a setup but forgetting the punchline. And without that shift, people tune out, your message gets lost, and your audience is left checking their phones, counting down the minutes ‘til coffee

Why Bad Storytelling is Holding You Back

If your stories don’t deliver that insight, people stop listening. They check their watches, nod politely, and mentally clock out. Your ideas don’t land, and you might as well be talking to an empty room.

How to Tell Stories Like a Comedian

Comedians know that setup and payoff are everything. They take the audience down a familiar path—then twist it. The next time you tell a story, don’t just list what happened. Lead people somewhere. Make them think one thing—then surprise them. Because the last thing you want is your audience standing around, waiting for something interesting to happen—like an extra in Top of the Pops wondering why an irate 80s pop star is yelling at them.