dick_costolo

Those who have seen Twitter CEO Dick Costolo speak know he’s a joke machine. But lately, he’s been getting a bit more love for it, thanks to a video of a one-liner-filled commencement address at the University of Michigan that has gotten a lot of attention in tech circles.

Costolo is, after all, an improvisational comedian. But Costolo isn’t just some guy who took a few acting classes in college (though he did), or even just perform at a few comedy clubs (but he did that too). He studied improv with Chicago’s venerable Second City troupe, famously a farm system for Saturday Night Live players. He mentions Steve Carell, Horatio Sans, and Rachel Dratch as a few of his troupemates.

Now, when you typically think of a CEO, you don’t usually associate it with the term “hilarious.” (Unless it’s something like, “hilariously inept,” but that’s a subject for another post.) But perhaps comedy is an under-utilized management style. The traits associated with being a good comedian – timing, adaptability, creativity – are certainly traits celebrated at great companies. At the very least, a comedic touch can bring lightness to a frazzled startup or corporate environment when things go wrong and are falling apart all around you. (Which is every day.)

There are workshops, like one called Business Improvisations, that teach improvisational skills to business students and executives. But not many CEOs of high-profile companies are known for employing such techniques in a big way. Costolo spoke yesterday at the National Venture Capital Association’s VentureScape conference, where he talked about a number of things, including managing a company as large as Twitter.

His comedic chops were on display, even during the fireside chat with Jason Mendelson, managing partner of Foundry Group. Costolo knows a crowd always enjoys a light roast, and it could be indicative of his management style at Twitter. “What’s your favorite thing about VCs?” asked Mendelson. “Paying for the second dinner,” Costolo replied.

Then Mendelson’s follow up: “What’s the worst thing about VCs?”

“Dinner.”

Raucous laughter from the audience. “I’m sorry, you set me up for that one,” Costolo told Mendelson. It helps to have a quick wit, especially when your entire company trades on quickness. Twitter’s great feat, after all, is its speed in disseminating information – as a makeshift breaking news outlet, or an emergency response vehicle.

But beyond that, it’s that approachable air that seems to work for a comedian in charge. When asked, Costolo said one of his best qualities as a CEO is how present he is with his employees, which he attributes to his background in theatre. Specifically, he says it’s a function of his improv training, in that it requires you to focus on what’s happening in the moment, and not just what the next thing will be. Doing that, he says, extends to really knowing your employees, and not just the managers that directly report to him.

“The view from the top is totally distorted. If you only spend time with people directly below you, you have no idea what’s going down in the trenches,” said Costolo.

As such, he mentioned teaching a class on management, so all the leaders across the company could learn how to manage in the same spirit. One thing he teaches is mixing it up. For example, he says, if he’s in a meeting and there’s some contention, he’ll get two people who don’t often work together – like the general counsel and VP of product engineering – and have them brainstorm a solution to suggest to the group at the next staff meeting.

Sounds a bit like improv comedy class to me.