From The Second City’s Dishwasher to EVP: Kelly Leonard’s Path of Persistence, Positivity and Acceptance Will Inspire You

Monday, May 6, 2019

By Miranda Myers, staff writer at Grow Wire

Since its inception in 1959, The Second City — a world-famous improvisational theater with roots in Chicago — has become known for its ability to produce comedic superstars like Bill Murray, Steve Carell and Tina Fey (amid countless others). On this episode of the “Grow Wire Podcast,” we sat down with Kelly Leonard, Executive Vice President of The Second City, to discuss his journey with the theater and why he thinks improvisation is key to success on the stage, in the office and in life.

Leonard takes us back to 1988 when he first got involved with the theater — a start, he admits, was anything but glamorous. His first job at the theater was as a dishwasher, and he insists that his gradual transition to Executive Vice President was based on two primary factors: luck and punctuality.

“I lucked my way into this,” Leonard jokes. “I showed up on time and was reasonably polite to everyone, so they gave me the gig, even though I was in no way qualified.”

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All jokes aside (which is hard to do in the world of improv), he explains that creating an environment where failure is not fatal was crucial to him becoming an important leader for The Second City. An open and understanding office environment allows creative ideas to flow more freely with no judgment on outrageous ideas that can lead to the occasional stroke of brilliance. 

“A mistake a lot of companies make is not allowing a space just to explore something that might sound a little crazy,” Leonard explains. “So if you say no to someone, they might not want to bring more ideas.”

"A mistake a lot of companies make is not allowing a space just to explore something that might sound a little crazy."


Leonard reveals his biggest goal within the company is to positively contribute more to the world through comedy and improv—the key to which is listening with an improv mentality of “Yes, and…” and a new idea Leonard initiated around bridging the gap between people with opposing ideas and beliefs; he calls it “Thank you, because…”

“I think if we can make people listen at least 2% better, then we’re making the world a better place,” Leonard declares.

Of course, we couldn’t do a podcast with Leonard and not get some hilarious behind-the-scenes stories—for example, how Bill Murray stole a rug one time…

Listen to the full podcast episode on Apple Podcasts, SoundCloud and YouTube, and as always, don’t forget to rate review and subscribe.