Kelly Leonard

405: How Improv Can Level Up Our Creativity, Connection and Leadership

Could improv comedy be the key to unlocking human potential?

Our guest today isn’t just tossing around this idea—he’s used the alchemy of the improv stage to forge groundbreaking strategies that are sure to ripple through business, sport, and life itself.

Let’s set the stage for Kelly Leonard. His title—Vice President of Creative Strategy, Innovation, and Business Development—only begins to capture his role at The Second City. And this isn’t just any theater. It’s a global comedy powerhouse that gave us legends like Stephen Colbert, Tina Fey, and Amy Poehler, to name a few. 

Yet the improv stage is merely a starting point for Kelly’s broader mission. He’s on an epic journey to inspire and empower people to use improvisation as a tool for positive change and growth. Kelly’s best-selling book, ‘Yes, And,’ and a pioneering partnership with the University of Chicago reflect this mission—bridging behavioral science with the principles of improv.

I love how Kelly offers us unconventional wisdom on reframing challenges, daring to risk, and savoring the present moment in all its unpredictability.

And our conversation goes deep. We explore thoughtful leadership, building a culture that unlocks radical creativity, tools to deepen relationships and even some remarkably profound ways to approach grief.

So, if you’re leading a team, wanting to live fiercely in the now, or simply searching for a fresh lens on life’s curveballs, this is one episode you won’t want to miss.

“I don’t want your success story. I want your fiasco, and the fact that you made it through. “

In This Episode:

What is ‘The Second City’?

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 people mostly know us as a place that is home to the first jobs of all these famous comedians. When I was washing dishes, Mike Meyers and Bonnie Hunt and Joel Murray were all on the main stage… And my first cast included Stephen Colbert, Steve Carell, and Amy Sedaris. I hired Tina Fey, Amy Poehler, worked with Mike Meyers, worked with Seth Meyers, Jason Sudeikis, Cecily Strong, Keegan-Michael Key, a host of incredible people… It’s just always been this place where budding talent is playing and learning and growing. And we have a school and we work with corporate groups and do all kinds of stuff, but at its heart, it is an improv based comedy theater.

Working well with others

Look, no one got into comedy, because they’re well-adjusted. That is not a reason people enter these doors. But what these skills do teach these individuals, these sometimes broken individuals, is how to work well with others. And when they share that language, they don’t want to ever do it differently. When I listed off that huge name of Second City alums, if you trace where their careers went, Second City, people went with them. Whether it’s Cheers, Mary Tyler Moore, 30 Rock Parks and Rec, writers, actors, everyone’s bringing the Second City people with them because they know that they have a shared language and a shared set of values. One of the things in improvisation is your job, because you have no script, your job is to save the person across from you, and you know their job is to save you. If you are going into these very high pressure situations and you know that this person has got your back and you’ve got theirs, why wouldn’t you want to be working with that person?

Creativity and innovation

The idea in creativity, of course, is you cannot be creative if you’re in judgment of self or judgment of others. You also can’t be creative if you’re in fear. And all of that is affected by people saying no to us. When you create a space, and this is what we do when we are putting together a Second City show over a 12-week process, first three weeks, four weeks, all ‘Yes, And’ every idea. I don’t care how dumb it is. Because you don’t know what innovation looks like when you’re being creative. And creativity and innovation are two different things. When you’re being creative, you are just playing and you’re failing and it’s all good. When you get to innovation, you’re turning it into something. But by virtue of it being innovative, it means we haven’t seen it before. If you’re saying no to these things, because they seem like they might not work, you’re being both anti-creative and anti innovation.

Leadership and teams

…in improv what we know is that leadership will change hands continually based on who has the ball and who’s the expert in that moment. We’ve all heard the phrase, “Your team is only as good as its weakest member.” At our place we say, “Your team is only as good as it ability to compensate for its weakest member because each of us will be the weakest member at some point…And that is true of all of us, so our differences as an ensemble, and that’s what we call our teams at Second City, ensembles, is that we’re all bringing this weird mix of talents and we are allowing each other’s talents to shine and then recede and shine and recede, and there’s flow that exists inside of this.

Coming up with good ideas

I think Bob Sutton’s done some at Stanford, which is to get to a good idea, you need something like 2,000 ideas. And I know that sounds daunting. It is not. If you just let your mind go. And the research I’ve looked at around when we talk about mastery in music and different arts is volume. I mean, the amount of music that the Beatles made in a nine-year period is stunning. Very similar to Beethoven and Mozart and the greats produced a lot. And we don’t talk about the stuff that maybe they produced that wasn’t great. It doesn’t matter, because a lot of the greatness came out of the a lot. 

What is ‘Yes, And’?

So, ‘Yes, And’ is an approach to additive creativity. You’ll never hear professional improvisers use the term ‘Yes, And’, but is the mindset of, I’m going to go in this room and I am going to allow every idea to live a little. I’m going to explore these ideas. I’m going to add to them. If they take us nowhere, that’s fine. We’ll go down another path. And we say in our work, you have to learn to replace blame with curiosity. So, this idea of it’s so easy to come in and be like, I’ve just been handed this terrible thing, but why not want to go, okay, I’ve been handed this thing, what can I make of it? We learn to see all obstacles as gifts. In improvisation we talk about that all the time.

On FOPO (Fear of People’s Opinions)

You’ve sort of seen the studies on fear of public speaking being one of the biggest fears that human beings have. So, I would imagine if you don’t have a script or anything or you don’t know what you’re going to do…That seems incredibly daunting. So, you really have to teach people the approach to make it not so daunting. So, a lot of that in very early improv classes is meditative qualities of getting that place of get out of your fear brain. We have them sort of fail over and over and over again. And then we work a lot on listening skills. 

The art of listening

When you’re on stage improvising with someone else, the last few words they say might contain crucial information. …But many conversations that we have throughout the day, we’re not giving our full weight to. And so when you practice listening to the end of a sentence and when you are patient and not worried about the pause at the end, that’s the other thing. A lot of people feel like, well, if I pause, that’s going to be upsetting. It’s like it’s the opposite. When I finished talking and I saw you sort of trying to calculate what you were doing, I knew you had been paying attention to me. I knew you saw me and that felt good. 

Practicing failure

And so they enter this world of improvisation in part because …they have to be deeply, fiercely present in the moment. They can’t linger in the past and they can’t linger in an imaginary future. They have to stay present. One of the things we say is you need to learn to play the scene you’re in, not the scene you want to be in. So, what’s the scene you’re in? Play that. And it is incredibly freeing. There are no phones. You have your other humans working with you. And in the classes we are putting people up to fail in volume over and over and over again.…And so you’re building up a callous for your bad failing work. 

The freedom in “not getting it right”

Nick Epley is one of the scientists that we work with at the University of Chicago, and he has research that shows us that human beings get it right in typical conversations, probably 20 to 30% of the time…So, when you understand that we’re getting it wrong more than we’re getting it right considerably, what an awesome, awesome opportunity for you to listen a little bit more deeply, ask a couple more questions, do all those things that might give you an edge in notch that up to 35 or 40%. And I would say that great improvisers are understanding what’s going on in a conversation or a room much more than a regular human being. And it’s in the same way that great athletes know to move to space. 

Following the fear

There’s a phrase in our work of the need to follow the fear. There’s a teacher, he was an actor here first and a teacher, Rick Thomas, who used to say, “You need to learn to fall into the crack of the game.” I’ll say it again. “You need to learn to fall into the crack of the game.” The idea there is these mistakes and these fears are all opportunities…All of that is about when you’re in this beaten space, but it’s also beatific and this idea of I’m leaping into the unknown. That’s where all the good stuff is. It’s hard, but it’s easier if you’ve got a group. It’s easier if you’re not alone.

Build a safe space to play and take risks

…we’re ruthlessly experimenting in front of audiences. We’re doing rapid prototyping of creativity in front of audiences, this third act of improvisation…The founders of Second City instinctively understood this idea that we need a safe space to play and to risk. This is the thing that businesses need. If they’re in the business of making something out of nothing, creating new things, all of that, where is their laboratory for people to play? Especially what we understand now in almost all businesses is you can’t do it in a silo and that you want to use your audience. How do you engage them in such a way that’s not going to put at risk your product or the thing that might not work? That’s not always easy, but I think great, great businesses have found a way to find that space of play for themselves.

On being human

Being a human being is not easy. I just turned 57, had a birthday last week. I am sorry to say this, it does not get easier. It really doesn’t. Your body starts to break down. You lose people. You lose more people. You lose pets. Work gets harder in all these ways. However, if you have a practice, and I do, we’re talking about it and hopefully some wisdom and you continue to allow yourself to be curious, you are going to have an incredible toolbox from which to deal with all this.

Relationships and loss

We lost Nora four years ago…and I’ll tell you the thing that if there’s one aspect of this work that through the sort of grief period that helped me, it was the idea of relationship, right? That in improvisation you have your ensemble, but your ensemble isn’t just the people on stage with you. It includes that audience and it includes the people who are cleaning up the room and the box office. And that’s the way they’ve always been. At Second City, we make heroes of the audience and in turn, they make heroes of us. And that’s what I needed. So I think it would’ve been very easy to just go hide in a hutch somewhere and instead we rallied the team and to hold us up when we couldn’t hold up ourselves. And they did it. It’s still hard. It’s not the scene I want to be in, but we had to play the scene we were in.

The role of AI in comedy

I mean, the thing that the robots are not particularly good at is improv or comedy… 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 because we’re all kind of just figuring this crazy thing out together. So the future is the blend. The future is not that AI takes the place of, it’s that AI is additive to, because you’re going to need the storytellers and the problem solvers and the creators, and that is just not going to be that particular kind of technology. And we are going to need deep places of human connection. And the surest distance between two people is a laugh.

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