40 min read

Learn to Fail (Kelly Leonard)

Being constructive, learning from failures, comedy, yes and, and mental flexibility.

Kelly is an author, radio host, and producer from the legendary The Second City theater where improvisation was born, applying it to business and behavioral science.

Listen and Read

You have two options…

  1. Get the audio at Apple, Spotify, Google, Amazon, and subscribe using your favorite app.
  2. Alternatively, you can listen and read this conversation using the basic player below.
PRO TIP: Subscribing has the advantage to avoid missing out on new episodes.


Simone Salis (host): Host of the podcast ‘Getting to Yes, And’ on WGN Radio and for Second City Works, Kelly is also a public speaker for the Aspen Ideas Festival, TED talks and companies like Microsoft and Coca-Cola. Kelly, executive director of Insights and Applied Improvisation, you are what Susan Messing, who is a long time improviser, would define as one of the guys who tries to turn improv into rocket science, and rightfully so. Because in the past 2 decades, we have much more research about what improv does to your brain and in like social environments. And you’ve been working on the Second City for 30 years.

Kelly Leonard (guest): Right.

Sim: And now you do this. But how did you start here 30 years ago?

K. Leonard: So my first gig at Second City was in October of 1988, and I became a dishwasher. So I didn’t come here looking for improv. In fact, I didn’t really know Second City did improv. I knew I came to the shows and I loved the comedy, and I had wanted to be a playwright. And so the advice I got from a number of theater professionals was, “If you want to work in theater, work in a theater. It doesn’t matter what it’s doing; whether it’s tearing tickets.” And I got to meet with Bernie Sahlins, who was the co-founder of Second City but, he had left Second City; had sold it to Andrew Alexander and Len Stuart, and he was starting his own theater called the Willow Street Carnival. And after I met with him, he’s basically like, “I’ll hire you to be a PA in my theater. But it’s not starting for about 5 months. I’ll call my friend Joyce Sloane at Second City, she’ll give you a job.” And I like I was on top of the world because I assumed of course I’d walk in as a marketing director. And no, I came in and showed up on Friday night and got shown to the kitchen by Allison Riley who was running in the rum. And while a terrible job, and it was back then, because it was like we serve basically you know like one draught beer. So I was basically… and we had the… the dishwashing were 3 brushes and I would just have to do these glasses over and on my hands are raw. And you could smoke in the theater in those days.

Sim: Oh my god! (Laughs).

K. Leonard: So just imagine this tiny cabaret theater with everyone smoking; it was terrible.

Sim: And beer. (Laughs).

K. Leonard: Yeah. But I got to see in that first cast was Mike Myers and Bonnie Hunt and also incredible talent. And I started to figure out that, “Oh there’s this 2 act scripted show, and then a third act that’s made up; this improv set,” and I started to understand what that was. Still, none of this was like clicking with me the like, “Oh, I’m going to do this,” it was more of like, “This is my way station. It is awesome and I’m getting no people for me to go write my plays and get out.” And that’s really, over the next couple years as I kept getting sort of promoted and working at the theater, I was still writing.

Sim: What did you get promoted for? Like, I mean, you were washing dishes well. (Laughs).

K. Leonard: Yeah. So I did a good job in the kitchen and I showed up on time.

Sim: Okay.

K. Leonard: And then I convinced Allison Riley, who is the house manager at the time, I said, “You know, I’m very good with people, I think I could be a host.” And then she’s like, “Okay.” So I trained… the guy I trained with, his nickname was Chainsaw, Chuck Mueller; and that was based on how he treated people.

Sim: Okay. (Laughs).

K. Leonard: Yeah, we were not known for our customer service at Second City in 1988 and ’89. I left briefly to go work for Bernie’s theater, it didn’t work; like the theater folded, I left like a week before that. But when I came back, I was about to get married. And the woman who ran the box office, Anne, was like, “Do you want to come work in the box office? Because I’ve got slots of feeling available.” I’m like, “I do, except my wife-to-be does not want me working evenings.” So she’s like, “Okay, well, what if… what if we do this? What if you worked Monday, Tuesday, Wednesday, Thursday during the day and then one night a week with me,” and, “would that work?” I’m like, “That’d be awesome!” Unbeknownst to me, what Anne had figured out is that Joyce Sloane, who is her boss, the producer of the theater, she liked me.

Sim: Okay.

K. Leonard: And Anne was like, “If I get like that someone that Joyce likes who’s in the office every day, it’s going to be so much better,” which turned out to be the case. So we start doing the schedule, I’m working in the mornings, it’s going well. Because Joyce was around every Friday night, we started the Kelly Leonard dinner club. So it was basically like, Joyce would take money out of the safe to give to me to buy a different ethnic food for all of us to eat in the office.

Sim: Okay.

K. Leonard: So it was like this really cool sort of communal group.

Sim: Yeah.

K. Leonard: I ended up getting married and Anne from the box office came to my wedding, and she caught the bouquet at my wedding.

Sim: (Laughs).

K. Leonard: And then I went to her wedding afterwards, and we’re all friends. And then Anne left to potentially go to graduate school. Actually, it didn’t, end up going to the Goodman. I became the box office manager after she left. And, again, I didn’t want to work nights, so I convinced Joyce that I should be box office manager and director of sales. So we’ll hire someone to really do the box office, and then I’ll do all this other stuff. And then Anne came back and then ended up working in the training center. And I’ll leap to the story. My marriage dissolved, her marriage dissolved, we’ve been married 22 years.

Sim: Right, because Anne from the box office is currently your wife.

K. Leonard: Yeah.

Sim: And also, not just that, you are her husband because she’s the head of the one program in comedy studies in the country, and I guess in the world in higher institutions.

K. Leonard: Yeah, she’s the brains in the family.

Sim: She’s… (Laughs). No, I… you know, you… the 2 of you  have been around the Second City for a little bit enough to understand that the 2 of… usually people in improv, you think about the performer, you think about the producer in the theater. But the 2 of you together are doing 2 completely different things and also, both of those are a different approach to improv in general.

K. Leonard: Yeah.

Sim: Because Anne looks at it from the perspective of someone that wants to teach it and methodically. And you look at… from what I understand, you take something that was created 50 years ago, has very simple principles that, throughout the years, created like incredibly funny comedians and everybody and as yourself. What is it that happens in the brain when we improvise and when we apply some powerful principles like ‘Yes, And’, for example, that not everybody might be familiar with? And how can we apply those principles and make people funnier more cooperative into a business environment; into a corporate environment?

K. Leonard: Or into all various life experiences. So it’s basically… what I’ve sort of… you know, this has been kind of a 3-year journey for me, so I’m just being able to kind of figure out what I’m doing now; in terms of talking about it. And so what I think it is, is essentially, I’m interested in the ways that we improvise offstage. Anne’s study is the way that we improvise onstage but then I use all the stuff she’s studying to go, “Oh, that works in this dynamic. This works in a corporate environment or a wellness environment, in a caregiving environment, in an educational environment, in a religious environment,” I don’t care. You know, there are rights and there are all sorts of connections. I talk a lot about failure and I talk a lot about innovation. And, you know, you’ve got to break eggs when you want to innovate, which means, you have to figure out how to fail in a way that can allow you to succeed. So one of the things that we’ve got at Second City is this third act, the improv act; the improv set where you can fail a lot in trying out your material. That’s one way to do it.

Sim: But it’s free, right?

K. Leonard: It’s free and it’s late at night and there’s all these sort of cues that, “It’s okay if it’s not as good.” But then you as a business need to give people permission to think risky and behave risky. And that’s not easy because we put constraints on ourselves all the time; we all do it. So one of the examples I give all the time my business talks is that, Mick Napier… Mick Napier started doing a thing in process which he called taboo day. And the idea was that, “You need to bring in the scene that there’s no way in hell we’d ever allowed to be on the Second City stage; it is either too offensive, it’s too expensive, whatever.” And with the shackles off, people brought in great scenes. And invariably, taboo day ended up yielding many scenes that made it into the show because people just made assumptions they shouldn’t have made. And I think for businesses, they need to take cue with that, which is like, “Why don’t you start a bad idea day where people bring in an idea that the company should not work on and that is not is off of mission or whatever?” You don’t know what you’re going to discover and you might discover some incredible stuff.

Sim: In your book ‘Yes, And’, there are a few moments that you talk about principles like this and there is a couple that really resonated with me. Because one is the need to be right.

K. Leonard: Yeah.

Sim: I still live with it. (Laughs).

K. Leonard: Yeah, we all do.

Sim: We all do, right?

K. Leonard: Yeah, I mean, we have an unquenchable need to be right. And Mick is someone who taught me a lot about this one. This is his… this is his thing. He sees it in people and it is very true. One of our… and for the behavioral science work that I do, we know that people’s default position is normally to do nothing or it’s to say, “No.” And also, we have a lot of sort of cognitive biases that make us believe things are true that aren’t. We tell ourselves stories to make our own weird opinions seem right. And so this need to be right is evolutionary; it functions in the brain and the body. But it is our enemy because we’re not right, we’re mostly wrong; and the world is mostly wrong. I think that can be a descent into madness for some people. Improvisation gives you skills and practices to make the idea that the world is a problem okay; that the idea is like you see all obstacles as gifts. It’s a very pro-social way of navigating the madness that is everyday life. You know, religions do this. This is not… you know, this is… we look for North Stars because we need them. Life is not easy to live, it is highly complex. I mean, if you just think about it, the fact that we’re not all crashing into each other outside on the street when we’re driving around is ama…

Sim: It’s a miracle. (Laughs).

K. Leonard: It’s a miracle! Like the way we’re distracted and it’s like, you know, and then we all get surprised when there’s a car accident; there should be car accidents all the time!

Sim: You have never been to Italy. (Laughs).

K. Leonard: I have been.

Sim: Oh, you have? (Laughs).

K. Leonard: Yes, that’s where I speak of. I mean, it’s the… it’s a worldwide phenomenon.

Sim: We do crash into each other a lot. (Laughs).

K. Leonard: You do crash into of each other; you do. And walking down the street, you could like… yeah.

Sim: You could kill people.

K. Leonard: Yes.

Sim: And it would be okay if you’re driving because you… anyways, sorry. (Laughs).

K. Leonard: New York, I mean, they’re like, “We get around.”

Sim: Yeah, true, true.

K. Leonard: So… so that is just highly true. And so with that being the case, what I have discovered is that, improvisational practice provides you all things you need to navigate uncertainty. And what they don’t… what it doesn’t do is negate uncertainty.

Sim: Mm-hmm, it acknowledges it.

K. Leonard: It plays… it acknowledges and it just and plays with uncertainty. One of the lines I use in my speeches is that, “Improvisation is one of those rare moments when you can mindfully linger inside a mistake. You can allow yourself to sort of take that mistake and work with it.” This happens all the time. I was just a preview performance of a piece that was terrible; it was a train wreck. And what I loved about our community is, afterwards, everyone like they’re laughing about and they’re like, “Okay, this is great. This gives us an opportunity to fix everything and make it better.” I’m like, “That’s not the way most people approach…”

Sim: Things.

K. Leonard: “… life and business,” and that, “they see a giant mistake or an error and they’re like, ‘We’re doomed,’ or, ‘We’re bad.’” And it’s like, “Man, we all… we’re constantly making mistakes. Here’s what you got to do, don’t make the same mistake twice.”

Sim: But you talk about in ‘Yes, And’ the ability… 2 different ways to listen. One is to listen so you can reply and then express your thought, and then eventually that becomes your ego that just wants to wait and get a chance to express your own thoughts. And the other one is listen to understand the person and whatever the person in front of you is saying.

K. Leonard: Yes.

Sim: And that… that makes… I mean, I am so terrible at it. But the first time I started improv, when I went there I was like, “Oh!” I started to realize that I thought I was incredibly special, and I still do, and whatever I had to say was incredibly special; which to an extent, you know, whatever we have to say is. But at the same time, just… now, I try to tell my brain, “Well, no, shut up! Shut up for a second.”

K. Leonard: Right.

Sim: “Listen and maybe whatever their person is saying is important.” Because if you’re convinced enough of your beliefs and like planted into them and also open to change them, you have the power to listen and the patience to listen for the other person. That’s what improv does.

K. Leonard: Sure. And, look, one of the most important ways you get to truth is through dissent. We really, as human beings, will fall into patterns that seem like they make sense, and then we say they make sense, and then we only find out later that they didn’t or something changed. This is the other thing that we keep forgetting is that, variables change truth. So what is… what was true, 20 years ago or 20 minutes ago might not be true today because of a series of variables that we don’t even see. Science gets proven and disproven and proven a disproven all the time. And… and that’s just one vertical; there’s many. And this idea around listening is first, making sure everyone understands that they’re terrible at it because most people don’t think that. They’re like, “I’m a good listener,” I’m like, “Seriously…” I mean, that’s why we run that exercise, Last Word, where, you know, if we’re improvising, if we’re talking, just talking, that you have to start your sentence and reply with the last word I say; and that requires you to listen at the end of my sentence. And what we find with most people when they do it, it’s like that’s a very unnatural… you know, they’re like, “Well, it breaks up the rhythm.”

“Like, yeah, it breaks up the rhythm if you’re not listening.” The idea of taking a breath and having a moment of silence for me to respond is not a bad thing. It’s not going to make you seem stupid, it’s going to make you seem reflective. And here’s where the behavioral science is really cool. What we’ve learned… and we have a… I’ll explain this.  I co lead an initiative called The Second Science Project with the Center for Decision Research at Chicago Booth. And we study behavioral science through the lens of improvisation. So we do research and we have labs and we create executive education programs; all that blend the knowledge that exists in academia on human behavior and our improv expertise in replicating moments of human behavior in these exercises. When we started talking to them about the principles around ‘Yes, And’ and our ‘Yes, And’ exercise, they got it right away. But one of the things… and now for those who don’t know, the ‘Yes, And’ exercise that we do…

Sim: Thank you. I was just about to ask you about just… just ‘Yes, And’, what is ‘Yes, And’ in 2 words? Becasue for you it might be obvious or…

K. Leonard: So the concept of ‘Yes, And’ is this. If you have groups of people making something out of nothing, that’s what improv is, a way to do that poorly or not at all is by saying, “No.” And you can’t just say, “Yes,” you have to say, “Yes, and…” you have to explore and heighten the thing that the person is saying to you. We have an exercise to sort of show this and we have people in a room and we say, “Hey, there’s a reunion that we’re planning for a year from now. Person A and person B are going to be having conversation, Person A is pitching,” where the reunion going to be, what we’re going to be doing. “Person B, your job is to say, ‘No,’ to all those ideas in as many ways as possible; go,” and we have them do that for a minute; it feels terrible. Then we have them switch places and Person B pitches about the reunion, and Person A’s job is to say, “Yes, but…” to this, and we have them do that for a minute. And we talk about afterwards and some people like, “I kind of felt better,” I’m like, “Yeah, felt better because you heard, ‘Yes,’ but then you’ve got the ‘but’ afterwards it was, ‘No,’ with a bowtie.

Sim: A negation.

K. Leonard: Yeah, come on. And then the third one is, we have them, “Yes, and…” So I’m like, “Sky’s the limit. Do not think about budget or any laws, just, “Yes, and…” every idea.” And invariably the sound goes up in the room, people are going crazy, are having sushi on the moon.

Sim: (Laughs).

K. Leonard: And so when we talk to the behavioral scientists, they’re like, “This was great.” So we… we lead them through this exercise and the first thing the scientists say is, “We’re… you’re doing it wrong.” I’m like, “What do you mean? This is like, “Yes, and…” exercise is, it’s the title of my book, we’re doing it right.” Like, “No, no, no, you’re doing it backwards. You should start with, “Yes, and…” and end with, “No.” And I’m like, “Why?” And they’re going, “Because of loss aversion.” Like, “What’s loss aversion?”

Sim: Yeah, what is it?

K. Leonard: So the behavioral science principle here it’s that, human beings hate losing things more than they like gaining things. We would rather… we are like we do not want to lose stuff.

Sim: Right.

K. Leonard: So if you take something away from me…

Sim: Right, I’m going to feel worse that if I just gained a million dollars.

K. Leonard: Yeah, if you’re taking away a million dollars, yeah. Or even $5.

Sim: Sure, sure. As long as… yeah, it’s not equal.

K. Leonard: So we’re like, “Okay, I actually see what you’re doing with that.” And then Mark Sutton, who was in this meeting is one of our corporate instructors, he tried it out with a corporate group and recognized we used ‘Yes, And’ at the beginning of the workshop to get us into a mindset of agreement. So he goes, “Well…” he came to the workshop and he had a look at his face. I’m like, “What happened?” he goes, “Well, they were right in the sense that the learning went way deeper.” I’m like, “Oh, okay, so we’re going to switch?” He goes, “No way, they were pissed off for the rest of the workshop, I couldn’t get them back.”

Sim: (Laughs).

K. Leonard: “We ruined them.” So I said to the scholars like, “Look, we’re… we get what you’re saying that we’re going to stick with the more performative aspect of our teaching.”

Sim: “So we’re going to have a good mood whatever we’re doing and they’re just ruin everybody’s…”

K. Leonard: Yeah, the science can wait.

Sim: “… life away and make them miserable.” (Laughs).

K. Leonard: Yeah, “We’ll talk about loss aversion later.”

Sim: Out of the experience, yeah.

K. Leonard: But then something really cool happened that was very positive out of this, which was they said, “Okay, but what’s the… what’s the fourth module? What happens when you have a argument or a disagreement or a disbelief between 2 people? How do you maintain some level of ‘Yes, and’ inside that?” And so what we came up with is, “Thank you, because…” The idea here is that, let’s say you’re an anti-vaccine person.

Sim: Sure.

K. Leonard: And that is not something I agree with.

Sim: How do you know?

K. Leonard:  You’re… (Laughs). So you’re explaining your anti-vaccine thing to me. My job is to thank you for that information which sets off a gratitude part of your brain, and then the crucial thing is the ‘because’. And then I’m going to be like, “And because…” and I’m going to state what you just said to me and why it’s important to you so that you feel seen and heard. Because as human beings, and this speaks to things like individuation and a concept called self-verification theory, we long to be seen as we see ourselves. And when someone does that, it’s immensely gratifying. And if I’m able to do that and then I share my truth with you and you… thank you because that, we’re going to stay in conversation even if we disagree. Trying to truly understand…

Sim: Right.

K. Leonard: … with appreciation, what you’re saying…

Sim: It comes from a place of honesty and not manipulation.

K. Leonard: Right. And then I’m going to share what’s true to me…

Sim: Okay.

K. Leonard: … in a… in a space that is… that if we can do that because we know we have each other’s backs.

Sim: Got it.

K. Leonard: That there’s… and by the way, these words are important because they are cues; the way you say something. So it speaks to a thing called framing. I had a… my friend who’s a professor at Harvard, Allison Brooks, once said to me… I said, “I get nervous before public speaking,” this was years ago before I did it as much as I do. And she said, “No, no, you need to say out loud you’re excited.” I’m like, “What do you mean? It’s like, “No, literally before you go on, every time you would say you’re nervous, say you’re excited.” And it worked. It was like this little nudge that like because you… the nerves are good, just like stress can be good to have you performed well. But you need to frame that into good stress where you need to frame that into good nerves. And part of that is just physically, you know, orally saying it.

Sim: Okay. I’m just going to name drop a little bit.

K. Leonard: Okay.

Sim: Because while we were talking, I remembered that Carl Vonnegut said that, “We…” he used it as an advice on something that might be dangerous. Like, “We need to really pay attention to who we pretend to be because that’s who we become.”

K. Leonard: It is the… there is…. I’ll put this way. There’s science behind, “Fake it till you make it.”

Sim: You know, there are 2 different kinds of stress. There is one that is productive and it’s because of excitement, and so you just try to reframe it.

K. Leonard: Right.

Sim: That’s what you do. You have… you have anxiety and you reframe it as excitement and eventually that becomes what you live and your truth and you start to enjoy it a little.

K. Leonard: Right. And that’s… I mean, that… that’s so much what happens in our improv for anxiety classes here is using the… you know, the these interactions are fraught with anxiety, not in the moment of doing, but in the moments before; sometimes the moments after. And so, so much about improvisation is about playing the scene you’re in, not the scene you want to be in.

Sim: Okay.

K. Leonard: It’s about being present and in the moment and sort of reframing the ‘before’ to empty yourself, a sort of a Buddhist thing.

Sim: Yeah,

K. Leonard: To simply let the moment be. We think things are going to be so much worse than they always are. We worry about these interactions, these difficult conversations, and our worry is way worse than whatever happens. Even in a bad encounter, often.

Sim: Right.

K. Leonard: It’s that… all that pre stuff. And that and that stuff of that anxiety of worrying about how something is going to go will sometimes make us not go and not do.

Sim: Right.

K. Leonard: Or it will get us so in our head that we do poorly. So it’s… it’s really about using… and this is what improv does, right? It’s all those stupid warm-up exercises that you’re doing that force you to look people in the eye, say words out loud, move your body, all these things that are essentially like practice for the difficult where we need to be our full human selves. And this is why this this work is so applicable to everything offstage, is because all it is, is human being practice and we don’t get human being practice as adults.

Sim: Yeah, we should have one hour in school growing up. It’s just like, “How to be human” (Laughs).

K. Leonard: We should have…. we should have one hour work every Monday and maybe every Monday and Friday that you open the day with like, “Hey, we’re going to do some exercises around listening to each other, around looking each other in the eye, around being present next to someone, about collaborating and a big group,” all these things that we have to do. You know, you’d never go to Second City and think that it’s okay if the actors don’t rehearse. You would never go to a symphony orchestra and think that they didn’t practice. And we say, “Why?”

Sim: “Why do we would walk in an office?”

K. Leonard: Yeah, “Why do we walk into an office where millions or billions of dollars are on the line and we think that none of those people need to practice?” And practice is not taking a ropes course once a year or one improv class once a year.

Sim: (Laughs). Yeah, one night at the escape room, that’s it.

K. Leonard: Yeah, exactly. That’s what they do.

Sim: Is this a job that you asked to have in the same way that you talk people into becoming the sales manager the director of sales?

K. Leonard: Kind of.

Sim: Kind of?

K. Leonard: I mean, you just… until you just said it like that, that’s not the way I thought. When I was when I wrote the book and I was having book tour, I was really like, “Oh, there’s a whole other world out here of people who are exploring ideas and concepts. And these are people that I read about in The New Yorker, and they’re interested in what I have to say and they think it has value,” and that was very gratifying to me. And meanwhile at Second City, there was a lot of change going on. And so, you know, we had some expansion and ownership, we had sort of some new management stuff going on. I was losing a lot of autonomy because then very much for most of my career, I was have left alone to kind of do what I wanted to do, and I think I’ll throw in a little midlife crisis, you know? Yeah, sprinkle that in, I’d lost both my parents and there was some other adversity. So I decided to make a move and I didn’t know what that move was

going be.

Sim: Of course.

K. Leonard: And luckily, Andrew Alexander of Second City saved me. And he’s done it over and over in my career; he knows it. And he was like, “I’m not going to let you quit Second City. What I’m going to do is, you’re going to hang out for a year and I’ll pay you as consultant, and you’ll use it as a bridge back or a bridge way.” It was the most generous and in smart thing that anyone could do. It was like, “Okay.” And it was the summer and he’s like, “Oh, let’s move your office because we’re going to have a new producing team that you’re not going to run anymore. So we’ll move you next to me,” which was great because it’s like that was the front of the building, this beautiful sort of window. So I moved all my stuff into the new office. Bob Knuth who works here was building me a pub table that was going to be a little area where I could have conversations like this. I went on vacation because I had pre-planned vacation, and then I get a call or a text I get from Nate Dufort who I worked with who said, “Your office is on fire!”

Sim: Yeah, there was summ… the summer that, yeah, the Second City went on the fire. And you still kind of had like… (Laughs).

K. Leonard: Oh yeah! No, this is…

Sim: The ceiling of his office is basically a plastic. (Laughs).

K. Leonard: Yeah, I had a plastic ceiling in this office which is not the office I was in because that one burned to the ground.

Sim: Right. That was… there was a historical… like is was in Altona in Chicago was like a kind of a historic landmark like all the earlier players of the Second City. There were also some apartments.

K. Leonard: Yeah, those were… yeah, Bill Murray had an apartment.

Sim: Right.

K. Leonard: So Second City itself did not burn to the ground but the center sort of office complex did.

Sim: Right.

K. Leonard: And so I lost everything in my office. So I needed to move to temporary offices because we couldn’t inhabit the building. And so the corporate group and the accounting group got moved to a shared office space, Regis was the name of the company; they were terrible.

Sim: Sure.

K. Leonard: And I was thrown in like in an office with like 4 other people. And Steve Johnston, who ran the corporate group, and I would see each other every day because these offices are tiny. And we’re friends but like we didn’t work on a ton of projects together. And he’s like, “If you were to do what you did for Second City all those years for the corporate division, what would you do?” And I did have an idea, I said, “Hey, I’ve been on book tour and I do a thing, and if any author tells you they don’t do this, they’re lying. When you’re on book tour and you go to a new town, you go to the local book store and see if your book is on the shelf.”

Sim: (Laughs).

K. Leonard: So I would do that and because I wrote a business book, I would go to the business section; which I never did before.

Sim: Yeah, of course.

K. Leonard: I mean, you know, I was a nonfiction guy. So I kept seeing all these books on negotiation and they mentioned how important improv was to a negotiation, but then everyone in deeper. Like, “What if we found an academic and we created like a negotiation improv workshop?” He’s like, “That’s a great idea, go do it.” So I Googled… go back to my desk and I Googled Academic Chicago negotiation. Five immediate professor show up; I email all of them. Four of them get back to me right away. I have coffee would like this woman from a Loyola, who I adored, and she’s like, “Let’s do it,” like into it. About 2 weeks later and I haven’t like… I haven’t gone out and done anything yet, the fifth contacts me, Eugene Crusoe from the University of Chicago. And he’s like, “Do you still want to meet?” And like old Kelly would not have met with him because I already had my people, but I’m in this sort of Shonda Rhimes ‘year of yes’ thing. And I’m like, “Sure.” And he goes, “Great, I’m going to invite my wife, Heather, who’s also a scientist up here to the meeting because I think she’d be interested.” And I get up there and I start doing my rap about improv as ‘yoga for your social skills’, how it’s allowed group mindfulness, and I’m talking about the work we do. And Eugene is kind of barely listening but Heather, his wife, is totally listening. And this is where this whole new thing started because Heather says to me, “Kelly, we’re behavioral scientists, we have decades and decades of research that show us that people make bad choices for themselves. You seem to have an art form in and practice that allows people to make different and better choices. Those 2 things have never been put together.” And that’s how the second science project started. It was… I was not there to go work with behavioral scientists, I thought I was building a negotiation and an improv thing. And this is such an improv moment because what I needed to be is simply open to the pivot.

Sim: Yeah.

K. Leonard: And the pivot was fantastic. And literally, this meeting was so well, like Heather and I connected on such a level, I… when I get home and I said to Anne, my wife, I’m like, “You need to come with me tomorrow to the University of Chicago to meet this person because I think I just met someone who’s going to be very important to our future.”

Sim: Yeah.

K. Leonard: And Anne’s like, “Okay, you’re very serious about this,” I go, “I am serious about this.”

Sim: Yeah.

K. Leonard: So we set up to have a coffee, Anne gets in the car, we go up and we had a 3 hour coffee with Heather; just, “Ping, ping, ping, ping!”

Sim: Yeah, yeah.

K. Leonard: And then as we’re walking away, I turned to her, I go, “I’m right, aren’t I?” and she’s like, “You’re 100% right.” And I’m like, “Okay, like we’re just going to do this,” and she’s like, “No, no, we’re… this is it. We have found our thing.”

Sim: Yeah.

K. Leonard: And that conversation has never ended. At that point, that’s when everything changed for me because the perfect thing was… so you… I needed that discomfort to allow me to think differently to discover a new pattern; it’s called divergent thinking. One of the biggest barriers to innovation is success, especially past success because you tend to do things the same way. And I’d had a lot of success as the producer of Second City; tons of hit shows, we did really, really well. I would have liked… I was doing these collaborations for different fine arts organizations; all went well. But I… but I may be hit stopped breaking true ground; maybe.  And this allowed me to really sort of think outside and think differently. So I kind of needed the discomfort to get me there. Then, we moved offices to the Chicago Tribune building. And my dad was a Tribune employee for 33 years. So I’m in a building… yeah, I’m in a building that I’m very familiar with, that I still have lots of people who knew him and knew me when I was like 5. I come back now and I’m talking to Steve and I’m like, “I got this thing at the Booth School of Business,” and he’s like, “This is great!” And everyone’s like, “Go for it. Yes! This is a fantastic opportunity!” And then, Steve and I come… we went for coffee and we’re back in the hallway and I run in to Todd Manley, who is the program director for WGN, he’s like, “Kelly, what’s going on?” And Todd, in addition doing that and he knew my dad, our kids go to the same school and he’s… he’s just a prince of a human being. And he’s like, “You should come up and like let’s talk at the offices at WGN.” And Steve says to me on the way up, he’s like, “You’re… I’m telling you right now, you will be on the radio in like a matter of like weeks.

Sim: (Laughs).

K. Leonard: I go, “What do you mean?” he goes, “I just have a sense about it.” And I’m not making this up, he’ll verify this. So then as we get through this conversation, at the end of it Todd goes, “Have you thought about hosting a podcast here?”

Sim: Oh, there you go.

K. Leonard: So that’s how that podcast thing happened; again, random… not so random but somewhat random encounter. So I’m kind of known in my family and my friends of being someone who can always get a parking space.

Sim: Okay. (Laughs).

K. Leonard: Like where there is no parking space, I get them.

Sim: Yeah, here are those people.

K. Leonard: That’s how I’m conceived. And Anne and I were at Stanford and we’re talking to my friend Tina Seelig who’s a professor there, and she was writing a book on luck, and Anne brought this up. She’s like, “I’ll tell you about luck,” and she goes… she goes, “I don’t think that’s luck. I think…” she goes, “I know Kelly a little bit and I suspect that Kelly assumes there is a parking space for him.”

Sim: (Laughs).

K. Leonard: “So he is open to the experience of there being one available, whereas a lot of us just assume that there’s no space.”

Sim: There’s no… yeah.

K. Leonard: And that’s a mindset thing. And so that’s… I think she’s right and I think that I pivoted myself to be open to any opportunity. And that’s kind of what’s happened the last few years. You know, we have created partnerships with a bunch of other organizations, interesting entities, interesting people, to bring improvisation to a lot of different areas. And it doesn’t seem to be stopping, it seems like there’s a thirst and an interest for doing this writ large. So if I’m looking at what the next ten years look like, it is an evangelical approach to improvisation, and then a very practical series of partnerships so that we can, you know, not just make this available to hundreds or thousands, but to millions.

Sim: There are those moments that you talk about like when you were talking… that with Anne… with Anne, you met…

K. Leonard: Yeah.

Sim: … somebody you’re talking for hours. The ability to recognize this moment’s, it’s such a precious things. Because I think that it’s even more important than skills, than practical skills or professional skills or abilities. Because sometimes we figure out something for the future then, the world, the universe, the practical life, whatever is the reason tells you, “No, don’t do that.” Or vice versa, you see something, there is a subtle suggestion that if you’re able… you have… you develop these small antennas on top of your head, that a great ability that impron can give to people and it will certainly make business environments and corporate environments better. How do you apply all the principles that you’re telling me about at the Second City?

K. Leonard: It’s a lot!

Sim: Because… yeah. Because the Second… it’s a lot and the Second City, at the end of the day, it’s a great theater, and you do this, which I think it has a pub… it’s almost a public service because whenever you allow society to understand and unlock disabilities, it’s great. But at the end of the day, the Second City is nothing bad with that for-profit company and business.

K. Leonard: Right.

Sim: And so you need to… do you apply your own teachings?

K. Leonard: Oh, yeah, on occasion I always say, “We’re doctors who smoke,” you know, we’ll be real good and then we’ll be real bad. We use it in so many different ways, and they’re broken down… I yeah I had to do this the other day where I made… they asked me to do hash tags for my podcast as it relates to themes for things we sell, okay?

Sim: Yeah.

K. Leonard: So how we sell at Second City. So I’m going to read the list to you because it’s in… way in my office in my desk.

Sim: Yeah.

K. Leonard: Storytelling, presentation skills, sales, marketing, innovation, creativity, team building, collaboration, ensemble, decision-making, leadership, education, learning, ethics and compliance, risk, diversity and inclusion, content, comedy, communication, harassment.

Sim: Harassment, let’s close on that. (Laughs).

K. Leonard: Well, yeah. We’re in the middle of creating a whole series of harassment videos for training. And the way we develop this is through this process called brand stage where we brought in a bunch of learning officers who have to do the harassment training. And we brought in a bunch of improvisers, writers, producers, directors, and we played with those ideas on stage with this audience of experts to find new truths; to find ways to talk about this really thorny, difficult subject area. Because the problem with all that training is, it’s so dry and people just check the box. And when they can have some humor or something funny or something, you know, edgy or unexpected, they’re going to pay attention.

Sim: The attention spikes up, yeah.

K. Leonard: We need them to pay attention because, honestly, you know, especially in this moment… alright so we’re recording this in April of 2018, the ‘Me too’ movement is a force to be reckoned with like I’ve never seen in my life; this period of time where women are finally being heard and men are finally listening in a way that we just didn’t. I’m a 52 year old, straight white guy who led an organization. And while I like to think that I was a good guy and an ally, I probably…

Sim: You still don’t have an experience that…

K. Leonard: I don’t have an experience.

Sim: Yeah.

K. Leonard: And I had no… the level of harassment and assault that my friends, my like closest friends, are now revealing to me that I didn’t know, it was like, “Shame on me for not knowing.” I mean, “Shame on me and all people like me who created a culture in which these people couldn’t speak up.” So I feel as if, especially right now, we need to use all our tools in our arsenal as human beings to fix these cultural norms that shouldn’t be normal. And they include those things that I just run off, including harassment, including diversity, including equity for individuals.

Sim: Did the Second City go through these transformations through the decades?

K. Leonard: Oh yeah. I mean, you know, we chat about this when you walked in, that Second City that I started at in 1988, for example, was highly homophobic. It was… it was… and I was so confused by that because I was a theater guy. We helped change that. I was part of the group that helped create the first outreach division here; the outreach division here in 1992. It was all and Andrew Alexander’s idea; wasn’t my idea at all. And he was adamant, and has been adamant, that we needed to get our cast gender equal, we needed more diversity. So we were, in general, ahead of it. We keep stepping on it ourselves and as an organization; no lie there.

Sim: Of course, yeah.

K. Leonard: We’re… you know, and the problem is, it is tricky, and times change around us and sometimes we’re late to catch up. So what we need to do as an organization is, you know, say we’re sorry when we make the mistake.

Sim: Yeah.

K. Leonard: Not make it again; we talked about that.

Sim: Right.

K. Leonard: And truly invite everyone to the table to help us as a community to move forward, to be smarter. And I think we limit our idea of what diversity is; because I do believe in cognitive diversity. I think, you know, this idea of that… that… and I believe gender is a spectrum, but if gender spectrum, so are thoughts; so are ideas. You know, what we have discovered it through both the improvisational work we do and the behavioral science is that, individuals contain multitudes. Like one of the reasons diversity training is so tricky and the sciences that mostly it doesn’t work, part of the problem is the noise. Because I have so many biases from for us to really understand the reasons I hate you or the reasons I’m you know scared of you or whatever. It could be because you’re a man, because you have a beard, because you’re from another country, because of your height, because of a thing that I ate before I came in here, it could be… right?

Sim: (Laughs).

K. Leonard: So there’s so many that, it’s not that racism doesn’t exist, bias doesn’t exist, it… way more than we think actually. But it is… you know, but what it is, is not something that I can diagnose just because I have an encounter with you.

Sim: I am Simone Salis and this is Hoomans. You can listen to every episode on your favorite podcast app or with a full transcript available on hoomans.org. Today’s guest is, Luca Badetti, professor of disability studies at Loyola and DePaul University.

The first time I came here to this agency was like 7 years ago and I, even I, noticed coming back year after year that, there was gradually more inclusion, gradually more diversity, and at least the search for that. Because that’s an effort that we need to do actively.

K. Leonard: Yeah, I mean, we still have you know basically industrialized racism in this country that we still need to dismantle. And the patriarchal you still rule… women don’t make as much money as a man; it’s fucking ridiculous! All of that, I believe is true. There’s people who don’t, there’s people who have other facts, that’s fine, that’s up for them. I tend to go with…

Sim: We say, “Thank you, and…” (Laughs)

K. Leonard: I say, “Thank you, because you’re you are getting your facts from what you think is a solid source.”

Sim: Sure, sure, yeah.

K. Leonard: For me, I think I’m getting my facts from a solid source. Maybe that’s the place we explore is, “What are the biases from the University of Chicago? Those scientists, what are the biases from the National Review or wherever you get them?” Because we should acknowledge that everyone has biases.

Sim: Yeah, of course.

K. Leonard: So maybe collectively, there’s a different truth out there that we can all discover. Maybe both things are true. You know, I mean, there’s all this kind of room to talk.

Sim: You know, there are a couple of things here. First of all, I’m always impressed by how it is hard to accept 2 truths at the same time.

K. Leonard: Yes.

Sim: That is stunning to me because like, you might be right and I might be right.

K. Leonard: Yeah.

Sim: And that’s okay. (Laughs).

K. Leonard: And that’s okay. We’re not programmed… I mean the…

Sim: Yeah.

K. Leonard: F. Scott Fitzgerald said, “The key to intelligence is holding 2 opposite ideas in your mind at the same time.” And I’ve always… that… that has stuck with me forever because I really felt that that’s such a key; that we tend to not think in terms of duality. We tend to… we’re very modal in terms of our like, “This is this one thing, right or wrong, black or white.” And we can be educated to understand that there’s always more than that, but I think we’re wired biologically to think about that one thing. And then we get into that pattern that, “There’s only one right answer,” and there’s many right answers.

Sim: Yeah, so you need to unlearn that; the need to be right.

K. Leonard: Yeah, mm-hmm,

Sim: And then eventually, you become able to a little bit at least try to listen to more than one truth at the same time. Diversity by ethnicity, gender, sexual orientation, is important in the Second City, and that’s visible; especially now.

K. Leonard: Yeah.

Sim: And that’s… this thing… really, it’s empowering. I tell you this, as a gay man coming from another country, it does make you feel accepted.

K. Leonard: Good.

Sim: And it does… and that’s a great feeling. Is that, as much as it is on the Second City stages also important to reach and management?

K. Leonard: Oh.

Sim: And is that where we are already.

K. Leonard: It is… it is vitally important and we are failing with that.

Sim: (Laughs). Why?

K. Leonard: I don’t know.

Sim: Are you failing..? Like are you talking about the Second City specifically?

K. Leonard: Yeah. Well, I mean, I think many companies are. You know, we are more diverse on the administrative side than we probably have ever been in our time; so that’s good. But still, the ratio sucks. You know, we… we have such… we’re gender equal on the stages and that’s been since the 90s.

Sim: Yeah.

K. Leonard: And I think, pretty steadily, we’ve almost been similar with regard to the kind of diversity you just spoke about, it has been those cast. That tends to be like almost half the cast has some orientation that is different than straight white cisgender men, you know? “What can we do?” And this is a conversation that is growing in terms of loudness and the ability for us all to sort of weigh in. What one has to recognize too is, we’re still undergoing quite a change at Second City as we sit here in 2018. So, you know, I led the organization as part of the executive… an executive team for many years. And, you know, that group is essentially gone; we have some new young owners. Andrew’s still here and Darcy Stewart is now here, Steve Johnston is now the president company, and these guys got to have time to kind of figure it out. We make the mistake of thinking, because we’re experts in one thing, we’re experts in another thing. So I think we do have an expertise in showing people how diverse teams work better. What we are not experts at is we can recruit and hire diverse teams to work as admin in the theater. We know how to… we know how to do it on the stage.

Sim: Got it, got it, got it.

K. Leonard: We have resources available to us to do those kinds of auditions.

Sim: Right.

K. Leonard: We’ve built-in programs to do that. We just haven’t done it on the other side, which is always where we’ve sort of, you know, struggled a Second City because our power is really what we do on stage.

Sim: Right.

K. Leonard: And, you know, the other side is sort of just, “I’m just here to sort of prop that up.” But as you become a bigger organization and you have, you know, more jobs and more people, you’ve got to become more… you’ve got to recognize more that you need to build up that muscle. So, you know, if you found an Achilles heel for the organization, that’s it.

Sim: I am… I also want to acknowledge one more thing about this. Because as you realize that… and, you know, there are constantly problems with… with this kind of social issues that reflect inside a company onstage and offstage, and it happens; it happens to the IO, it happens to the Second City. But if you go through the archive materials, old show… like old, old material like Nichols and May, like that kind of stuff, you notice that the Second City kind of evolves. And sometimes it might be late, but it kind of… it has the ability still to notice a social change and acknowledge it; first through comedy and eventually also through practical…

K. Leonard: Yes.

Sim: … stuff because the equity fight, the Union actors, whatever change at this company, it was also like through comedy partially. You talked in your book about like some jokes made in front of the president and the owner about health care for all the employees, and that kind of stuff. So is that the power of the ensemble versus team that you talked about also in the book?

K. Leonard: I think so, yeah.

Sim: You explained that, instead of having working teams, an ensemble works like in concert or theater.

K. Leonard: Yeah, we have a great phrase the… the, you know, the cliché is, “Your team is only as good as its weakest member.” And what we say is, “Your ensemble is only good as how good is its ability to compensate for its weakest member.” And the idea there is because one of us is going to be the weakest member at a different time, depending on what’s going on, and, “Shouldn’t we all lift each other up?” And the other the other version of that is that, “No, there’s someone who’s always the worst.” And generally that is the person who doesn’t look like us.

Sim: (Laughs).

K. Leonard: You know, so get out of that orientation.

Sim: Yeah.

K. Leonard: And you when you truly exist inside an ensemble orientation, you have certain values and certain ethics and certain behaviors that we’ve agreed are better, so let’s all do that. And we don’t… the ensemble can sort of you know self-regulate itself in a very powerful way. So I do think that ensemble helps play a part in that. There’s… there’s more at work. You know, what I’ve noticed is… so because I host my podcast, I get to… I’m reading a book or 2 a week. Usually around some sort of social science or some psychology or some neuroscience or thought leadership or whatever. And there’s common themes that run through a lot of… a lot of this. So some of them are like, “Multitasking is a myth.” We demand of everyone who works here on the admin side that they have to multitask like crazy. That is insane because it’s scientifically disproven. You can’t do it. So we have cognitive overload problem, we got to figure that out. Another theme that comes up is, “Happy workers who understand a purpose, a reason why they’re there, are more productive.” We’re generally good at that, except when we’re not.

Sim: (Laughs).

K. Leonard: You know, and you having been in the building, know exactly what I’m saying.

Sim: Right.

K. Leonard: Like there… when a show is cooking and everyone’s sort of talking that that’s like, “Man, this place is magic, everyone feels it.”

Sim: There is that energy in the air that makes you feel… it’s more like synergy in the air, not just energy.

K. Leonard: Yes, yes, it’s synergy in the air; yeah, that’s it. And like during the summer when the summer camps are going on, all these kids are here taking classes, you can’t come through this and not be in a good mood. I mean, it smells bad and, you know, someone’s having an attack.

Sim: (Laughs). That’s hormones. (Laughs).

K. Leonard: Yeah, that’s hormones. But it’s really cool; so that’s… that’s a theme that is true scientifically and true experientially with us here. And the… here’s the other big one which is, “Hierarchical leadership doesn’t work, flat organizational structures are better.” We all know this and actually, we’re good about knowing this at Second City because we do try to give autonomy to our different, you know…

Sim: How many people are employed by the Second City, sorry?

K. Leonard: Thousands.

Sim: Well…

K. Leonard: But full-time…

Sim: Full-time members in…

K. Leonard: A couple hundred.

Sim: A couple hundred.

K. Leonard: Yeah. And they’re probably in this building. Yeah, no, couple hundred. Across the whole business, 250 or something maybe in the building and 150… I’m not sure. It’s hard. It’s hard to… because we fall into the hierarchies and we crave leadership. And you need leadership, it’s not say leadership doesn’t exist.

Sim: Right.

K. Leonard: But you also have to give yourself permission to be your own leader. There’s a phrase I’ve been using a lot with our team here which is, “You need to replace blame with curiosity.” So if our boss is calling us and saying, “What our ticket sales tonight?” you’re assuming he’s calling because he thinks they’re low and he’s worried about it, but what if he’s just curious about it?

Sim: Mm-hmm, like there is no negative thought attached, and like that is basically your mind already going into survival mode…

K. Leonard: Right.

Sim: … with no one negating…

K. Leonard: You’re running from the panther.

Sim: Right, exactly.

K. Leonard: So… and we do that. And so what we have… what a number of people when I brought this up started applying it and they have it written up in their office or whatever, is that

they’re like, “It’s helped me. It’s helped me not be so…” and then it goes back to it because then, you know… and sometimes it… sometimes it is blame.

Sim: Take improv classes there across the corridor. (Laughs).

K. Leonard: Yes, yeah, “Just hop upstairs, jump in.” But it does because it does become tough because we all do it. You know, we get into our blame mode.

Sim: Yeah.

K. Leonard: So we have to remind each other, and as a good ensemble, we have to remind ourselves that we have this this code, and when we violate the code, it’s up to the ensemble to correct it. And that’s hard because it hard to tell your bosses when they’re doing bad work. But you can do that with love. I mean, there’s no reason you can’t… I mean, you know, if we’ve got each other’s backs, we’re all in this for the same reason. And the people I know here, like I have been through crisis, tragedy, tears, divorce, death, with all of these people. And they have done like, without getting into like maudlin specifics, like they’ve shown up on my doorstep when things were the darkest. And a bunch of us have done that for each other and we just kind of know it. Bnd but we do take it for granted and we forget, it’s like, “Look, we’re not perfect and we make our mistakes and we yell we shouldn’t we’d all do that.” But as long as we then agree to these basic principles and we say we’re sorry and we find our way back, I think we’re going to be okay.

Sim: Acknowledging mistakes, and that’s where improv teaches and that’s what maybe, you know, is it too cliche or maybe the next book is going to be like ‘Improvising life’ because it looks like you’re starting to… (Laughs).

K. Leonard: That’s funny. I actually thought about this. Because Alan Arkin titled his memoir ‘An Improvised Life’, I can’t use that one.

Sim: Oh, I didn’t know. (Laughs).

K. Leonard: I literally thought about this in the shower. Because I have this idea for the next book and I’ve actually have an outline for it and I’m like, “It’s… is it more ‘Yes, And’ or is it more of, you know, ‘Yes, And’-ing your life?”

Sim: It’s because… yeah. I think… I think you’re starting to…. yeah. I think whatever you notice with and…

K. Leonard: Not a guru.

Sim: Not a guru; not a guru.

K. Leonard: Not a thought leader.

Sim: Just a guy that is trying to do his best. (Laughs).

K. Leonard: Yeah, just a guy trying to do his best. I love that!

Sim: Alright, Kelly Leonard, today at Hoomans. Thank you so much Kelly for taking the time and chatting with me.

K. Leonard: Lovely to be here, thanks.

Sim: Thank you.

P.S. Did you enjoy this? Subscribe to the 🎧 Podcast and get new episodes first with the 💌 Newsletter.