I workshopped a comedy bit with singer Mat Kearney

Ten minutes backstage before a conference

Earlier this week, I was backstage at a conference in Austin with singer-songwriter Mat Kearney.

Photo by Breezy Baldwin

He was the opener (musically), I was the opener (keynote-wise). We had about ten minutes before the show started and instead of talking about the event, we spent the whole time workshopping one of his comedy bits.

No, Mat isn’t also a stand-up comedian. He’s just learned, as a musician, adding humor to his live shows is a great way to engage the audience (and there’s something special about getting a room full of people to laugh).

In fact, he told me one of his biggest focus areas for his last tour was working on the bits between songs. Not the music, but the moments in between.

In particular, Mat had this story he’d been telling on stage about one of the first times he heard his own song playing out in public. He was at Home Depot. His song came on over the speakers. So he turned to the guy next to him and said, “Hey, that’s my song playing.”

The guy looked at him for a second and said, “Do you know if this 3/4-inch pipe fits a toilet flange?”

It’s a great bit that already works. But Mat said he always felt like there was more there. So we kicked around a few ideas backstage using a concept I learned from UCB: “If this is true, what else is true.”

What if he follows the guy around the store, helping him shop, but really just trying to get him to acknowledge the song? What if he goes up to other shoppers and they all just want his help finding things? What are other places he’s heard his song and how did people react there?

What a musician can teach you about humor at work

What I love about this story is the approach Mat took to the craft. He already had a bit that worked and he could have left it alone. Most people would have.

But he treated it the way he’d treat a song. You write the first version, you play it live, you hear what lands, and then you go back and make it better.

That’s what practicing humor actually looks like. It’s not sitting in your office trying to come up with jokes from scratch. It’s noticing the thing that already got a laugh (the comment in the meeting, the line in the email, the observation you made at lunch) and asking yourself, “What if there’s more there?”

If this is true, what else is true?

That question is one of the most useful tools in improv and sketch comedy. And it works just as well in a conference room as it does on a tour bus. You don’t have to invent something from scratch, you’re simply building on what’s already working.

Mat didn’t become funny overnight. He noticed that audiences responded to the moments between songs, and then he started treating those moments like they were worth practicing.

After our impromptu writing session, Mat kicked off the conference with a beautiful song. Then I went on to teach the audience some of the same skills Mat and I were just using backstage.

The skills aren’t different. Whether you’re a musician trying to connect with a crowd between songs or a project manager trying to keep a team engaged during a status update, the process is the same. Notice what gets a reaction. Ask what else might be true. Try it out. Refine.

So here’s what I’m curious about. Hit reply and tell me: what’s something you’ve said at work that got an unexpected laugh? The offhand comment, the accidental joke, the thing you didn’t plan that landed anyway.

I want to hear it. And I bet if we applied “if this is true, what else is true,” there’s an even better version waiting.

Wit regards,

-Andrew

P.S. If you’re not familiar with Mat Kearney’s music, do yourself a favor and check him out. I’d start with “Ships in the Night” or “Nothing Left to Lose.” You’ve probably heard his songs without knowing it, possibly while in a Home Depot.