How Improv Can Level Up Our Creativity, Connection and Leadership | Kelly Leonard, VP of The Second City

Kelly Leonard (0:00)

I don't want your success story, I want your fiasco in the fact that you made it through. So when I think about comedy and improvisation, I think about mess and struggle and hard stuff, and the ability to navigate through it and laugh our asses off.

Michael Gervais (0:28)

Welcome back or welcome to the Finding Mastery Podcast. I'm your host, Dr. Michael Gervais, by trade and training, a high-performance psychologist. And I am thrilled to welcome Kelly Leonard to the podcast for this week's conversation. If you've ever appreciated the comedic stylings of talents like Tina Fey or Stephen Colbert or Amy Poehler or Seth Meyers, you may want to give today's guests some credit. As the executive director of Learning and Applied Improvisation at Second City, the world's premier comedy theater and school, Kelly Leonard has spent over 20 years shepherding the kind of creativity and collaboration that not only catapults comedy legends, but has the power to transform people's lives.

Turns out, improv isn't just good for laughs. Looking at behavioral science through the lens of improvisation, Kelly helps not just build performers, but leaders, innovators, and everyday professionals develop transformational skills in business using the yes and principle, mastering the art of co-creation, leading by listening, and innovating by making something out of nothing. Like improv, life is not scripted. The more tools we have to navigate it, the better. So whether you're ready to laugh or learn or cry or a bit of all three, you're going to love hearing the insights in this remarkable conversation. So with that, let's jump right in today's conversation with Kelly Leonard.

Kelly, I am stoked to learn from you today and just a sincere thank you for coming on the podcast with us. But before we dive into your insights, can you just set the scene for our audience and explain what Second City is, your roles there, and then please feel free to name drop all of the amazing people that you've been able to work with. But like, so can you just give us a flyover?

Kelly Leonard (2:27)

Yeah, yeah, yeah. So, and maybe we can do this. I can sort of tell you my story at Second City and we'll explain what Second City is through that. Because my first gig at Second City was in 1988 I had just graduated college and I got a job here as a dishwasher.

And the other guy who got hired that week to be a dishwasher was a guy named John Favreau, who would go on to direct some pretty famous films. We also both had mullets and my wife has photographic evidence of such.

So Second City is a sketch...

Michael Gervais (3:00)

Wait, hold on, hold on. I can see where we're starting already.

Kelly Leonard (3:02)

We're starting with mullets.

Michael Gervais (3:04)

You and John in the kitchen.

Kelly Leonard (3:06)

Washing the dishes.

Michael Gervais (3:07)

This is perfect.

Kelly Leonard (3:09)

With a bunch of like Yale sociopaths and alcoholics.

Second City is a renowned sketch and improv theater. It started in 1959 And so when I showed up, it was legendary in Chicago and nationally. And we have had a theater and still do in Toronto when we produced a television show called SCTV. And people mostly know us as a place that sort of is home to the first jobs of all these famous comedians. So when I was washing dishes, Mike Myers and Bonnie Hunt and Joel Murray were all on the main stage. Jane Lynch was in our ETC stage, our second stage. And then a couple guys named Tim Meadows and Chris Farley had just been hired into the touring company here.

And the way Second City is set up, I don't know if people know this, but we do two acts of scripted content, the review, and a third act almost every night that's fully improvised. And that's where the cast is just taking suggestions from the audience and making what appears to be magic happen on stage. And lots of celebrities will join up. It was not uncommon for Robin Williams to stop by almost every month and perform with the cast in the improv set. And the improv set is free. So, you know, broke college students are coming to this and getting to see world-class talent. And the thing is, it appears to be magic.

And then you work here for a while and you realize there's a sort of improvisational pedagogy that is going on, that all our performers are steeped in, that they learn.

And what I sort of figured out is that improvisation is not magic. It's like yoga for your social skills.

I often say it's like loud, noisy group mindfulness, right? It's a practice in being unpracticed, which is the way all of us walk through the world. So, you know, the very first company was spitting up people like Mike Nichols, Elaine May, Alan Arkin, Barbara Harris. Then you've got people like Peter Boyle and Joan Rivers and Robert Klein and Fred Willard. And then the group in 1969, which called itself The Next Generation, included John Belushi and Harold Ramis. And then you've got John Candy, Gilda Radner, Catherine O'Hara, Eugene Levy, George Wint, Jim Belushi, Bill Murray, Betty Thomas.