The Intersection of Improv and Business: Full Episode Transcript - Kelly Leonard’s Introduction

Hello. Welcome to Question Everything. Today, I am joined by Kelly Leonard, who is a longtime creative executive at the Second City, where he hired and or developed shows with, you know, people like Tina Faye, Stephen Colbert, Seth Meyers, Steve Carell, Keegan, Michael Key, Amy Poer, and so many others. He wrote the bestselling book Yes. I am a huge fan of it, and he hosts the Getting to Yes podcast for Second City and WGN Radio in Chicago. Welcome, Kelly.

Thanks for having me.

Ugh. I am so excited. I've been counting down the days until I get to meet you virtually, kind of in person, it feels like these days. So I have a story I have to tell you. 

Yeah, Let's hear it again. 

Like my journey to Yes. And into Second City. So I have been running business development and marketing teams for, let's just call it, like 10 years. Mm-Hmm. And so my job is to meet new, new CMOs, new clients, share with them a recommendation, and get them excited about my company, and get them to say yes. And so just imagine I'm in a huge conference room that's very long. There are about 20 executives lining the sides of the table. The room is pretty dim, and I've got all of our executives up, up at the front, and we're presenting a 75-page deck to this crew. Mm-Hmm.  about halfway through it, I look over the CMO is asleep.

All right. That is not a good sign, problem number one. 

Problem number two: we didn't do anything about it. We just kept going slide after slide after slide. We all froze. We just thought it was more important to keep pushing through our content. The content we thought was important, instead of changing our posture, changing our tone, maybe inviting them into the conversation. And I realized at that moment that we didn't have the skills to do that. It was something I lacked. I was a great presenter. My team was a great presenter, but when it came to creating that interaction, we just could not do it. And so I went home that night and I, I just started researching like, what is it that I'm missing? And I came across improv in Second City. And I started to piece together all of the connections between improv and business. Right. And it was so clear to me that it was those fundamentals that I knew were gonna dig into today that I did not have those types of things I was afraid of. And I know my team was, too. And so we embarked on a year-long study with Second City, and I took about 20 executives with me. We went to Chicago, we got to go on stage, we got to see performances in our final session, and we actually held our own improv at our company in front of 200 of our employees. And it was remarkable. I still use and implement the lessons that I learned today.

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The Intersection of Improv and Business: The Power of Improvisation with Kelly Leonard

I love that. It always amazes me. I was just up in Toronto at a learning conference, and I spoke in the afternoon, but in the morning, I kind of didn't have anything to do. So, I hung out at our booth. We had a booth, and I'm like, I'm gonna work the booth. And so many people would come up, and they'd be like, oh God, I love Second City. What are you doing here? And I'm like, really? I'm like, do you know that you don't know that we do education? I guess, I guess I might've known you did some classes for people who want to get on stage. And then the simple question is this: do you think people in business need to know how to improvise? And everyone said yes. I, I don't, like, you would have not to know what improvisation is. And so it's making something out of nothing. Do you need to do that in business every day? Every day, every day? So the idea of then how about working with the people who are, by far, in a way, the biggest brand in this work, the, the greatest history who've been at it for over 60 years. And, and, and then that, it makes total sense. But it's interesting that we're such a well-known entity that this aspect of the work is still a secret.

It's surprising to me, too. And I can tell you that after we went through our session, our pitch rate went up, our confidence went up. Mm-Hmm. , I mean, it impacted so many things, even how I would structure teams. And so, the parallels are insane. And I can't wait for our listeners today to take some of what they have learned with them. It has been said that 30 seconds in a room with Kelly will make you wiser. And so, I don't even know what's.

I dunno who said that. I honestly dunno who said that?

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

The Intersection of Improv and Business: Navigating Generations and Trauma —  Insights from Kelly Leonard

Somebody very wise. Okay. We get at least 30 minutes with you today, and I'm pretty sure we're going to be changed entirely humans after this. I know you have trained some of the most amazing comedians and actors in the world. You've authored a bestselling book and have your own podcast. What are you doing right now? What's kind of on your agenda lately?

Well, I don't know if you heard about The Pandemic, but there was this thing that reduced Second City to 39 people, which was wild. And I was one of the 39, thank God. So coming and we got sold. So, I've worked here for 34 years, and this is the first time I've had new owners and a new boss. So we're kind of still rebuilding. And my job is certainly some of the things I have been doing already. Right. So I work a lot with academia, in particular, the behavioral science community, to build those bridges between evidence-based research and what it is we do at Second City. Primarily improvisation, but sometimes venturing into our work in comedy. I'm also consulting with a professional company on new show ideas.

But I'll tell you two things that sort of have come up recently a lot. One is clients talking to us about getting help with the various generations in the workplace. So it's the first time ever that we've had five generations in the same workplace. And that's astounding. And although there's more that unites us than goes the opposite way, I, there's tension, and people feel it. The idea is that it can sort of be a playful human intervention help, which is what Second City does. So, these exercises allow people to embody what it means to communicate with someone who's different from us or we perceive as different from us. It may be just that the words, language, or style that they present are unusual but maybe not that different. So that's, that's one thing we're working on.

Kelly Leonard continuation story: 

And then the other, and this just keeps coming up, and I know I'm a comedy guy, and I know we wanna keep it funny, but I've been talking to organizations and saying, what's your number one issue? And they go, trauma. I'm like, all right. Yeah. Well, I get that. So, the idea we have all been through, not just COVID-19, this was existed before we all went through our trauma. And I stumbled across, not quite stumbled, but I interviewed my friend Scott Barry Kaufman for the podcast, who's a wonderful scientist and thinker. And he wrote a book called Choose Growth. And he had a quote, and I've been using it a lot with clients. And it's by Irvin Neilam, who's a cognitive psychologist. And he says, sooner or later, you have to give up the hope for a better past.

Kelly Leonard continuation story: 

And I find that profound. Yeah. I find it profound in the sense that we do linger in the past, we ruminate, and we can't do anything about it. Mm-hmm. And we have a phrase in our work that you need to play the senior in, not the scene you wanna be in. And so this idea is how can we get you to not disassociate completely from the bad things that happen to you, but let go of living in the bad things that might have happened to you, and also don't linger in this future that may or may not exist in the way that you're dreaming of it. What does it mean for me to be fiercely present with Ashleigh right now? And if I'm doing that, that feels good, and it's interesting, and I'm gonna learn something and, and we are gonna be better for it as, as I think, human beings together. Because, you know, we have another phrase in our work that all of us are better than one of us. It's like, if I'm the smartest person in the room, I'm probably in the wrong room. So, I want to make sure I am getting the most out of my scene partner. So that's what I do on stage, but that's, that's what's existing right now when the two of us are having a conversation as well.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Empowering Yourself for Success

Alright. There are so many lessons, and we haven't even gotten to the first question yet. That's great. I connect to that on so many levels, personally and professionally. I think there's a lot that you can let go of and free yourself from to create some space to live right now. Also, dream about the future and start putting some of those bricks or things in motion right now that can get you to the future that you want.

Kelly Leonard’s take on dreaming about the future: 

Yeah. But you're not gonna be building if you're dreaming, and there's a place for dreaming, there's a place for mind wandering, all those things. But, recognizing that you have some agency over this and if you're denying your own agency, Yeah. That's, that's the worst. Because you aren't going to do this alone. So not only do you have to recognize your own agency, you have to inspire others to want to work with you. And that requires, you know, good storytelling. That re requires an understanding of some influence. It also requires giving up some ego because you have to make space for others in these conversations and ideas with the things that you hope to build. 

I really appreciate that. One of my first early mentors told me, I think I was an intern for her, that when you get to a position where you can start to hire, make sure that you're hiring people that you would be afraid could take your job someday. Yeah. If you surround yourself with that level of talent, you'll succeed in everything that you do. And it's been a mantra of mine, really, since the beginning.

Kelly Leonard shared how Second City was built:

Yeah. Well, that it, you know, my first cast at Second City had Steve Carell, Stephen Colbert, and Amy Sedaris. It was 1992. Yeah. And, and, and watch, I mean, like, they weren't scared of each other. They were just building work, and they were building comedy and relationships. And it was amazing to see how that worked. And there was, this is what's fascinating just about Second City alone, is that, yes, we produce star after star after star in an art form that is completely about making your partner look good. That is just not at all about pushing yourself forward. And so the lesson there, to me, is a real easy one to get, which is if like, you can make yourself shine by making others shine. And that's just such a pro-social positive way to look at the world. And it's one of the reasons that when I give talks all over the world talking about this stuff. Everyone's like, can you please talk to our politicians? I'm like, yeah, I get it. I mean, I just don't know if they're going to listen. 'cause So far they don't.

Oh, man. That's living in the future.

Yeah, that is living in the future. Let's hope that's the case.

Yeah, let's hope. All right. Well, we've got 12 questions up on our game board today for Kelly. So, I guess I'm going to find out what your favorite number is. You get to pick your favorite one first.

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The Intersection of Improv and Business: Leadership and Vulnerability — Insights from Kelly Leonard

Favorite number six.

Number six. All right. The most powerful way of getting people to laugh is by being truthful. And I think you've said that requires a lot of vulnerability. Yeah. So in your opinion, what can leaders do to best show their vulnerability? I think it's a really hard skill sometimes for leaders to expose, yet it's so important.

Kelly Leonard’s answer to what leaders can do to best show their vulnerability: 

Yeah. It doesn't, doesn't have to be hard. So, first of all, no one is interested in your success. I want your fiasco. That is what is interesting to me. It is what is funny to me. It's the story I want to hear. And part of the reason we want to hear it is we want to, we wanna see that you overcame that thing. So, really inspiring leaders do share their struggles. We co-created a course at the Farley School for Entrepreneurship and Innovation at Northwestern University with Sunil Gupta. Sunil wrote the book Backable, which is about his journey trying to get funding for the Rise app, which he didn't get at first. And he tells this fantastic story in the book. So, let me back this up. Sunil is out trying to get funding, but doesn't get any. He gets a call from the New York Times, and they're like, Hey, we wanna do a feature based on the struggles you've had. And he and he is invited to speak at a thing called Failure Con. So he goes and talks about his failure. And then the piece New York Times is his picture underneath a banner that just says Failure.

Okay.

Kelly Leonard's continuation response: 

And so he did all this research about what is it that can make someone be backable? The story he tells in his book is about a young woman who grew up in utter poverty in the border, in a border town between India and Pakistan. No running water, no electricity. They had one kerosene lamp, and she had one book. And the book was a biography of Henry Ford the automobile pioneer. Mm-hmm. And she was obsessed with Ford and cars. And she dreamed of being an engineer. That was the thing. And this is in the sixties, like early sixties. Yeah. Her parents somehow raised enough money to send her to the University of Oklahoma. And this is 1962, and they send her on a ship. She's never been away from this town. And she goes to college, and she studies incredibly hard.

Kelly Leonard's continuation response: 

She ended up getting this engineering degree, and she sent a letter or a telegram to Ford Motors for an interview. And because she had an unusual way of thinking at that time, her last name, they didn't recognize that she was a woman. So when she shows up, the hiring person says, oh, I'm sorry, we don't hire female engineers. And she's about to leave. She decides to tell this guy her story about how she grew up in this town, a small village. And she would read this book, and that was her dream. And she said to him, I get that you have never hired a female engineer, but what if we made history today in 1966, and you did hire the first female engineer, and he did? Ugh. And that is Sun Neil's mom.

Wow. The reason he tells the story is because that was the story he would tell when he went back out to get funding for the Rise app, which he got. And a lot of people, when they asked them like, why'd you fund it this time? Like, a story about his mom? And it was this idea of, like, he comes from a place, and he comes from her. And there was a struggle. And if this idea of lineage, this idea of where we come from, this idea of struggle, all these things are so important when we are telling the story of ourselves and why other people should back us. And when we were teaching this to these engineering students at Northwestern who'd never been taught storytelling, why would they think that's important to the machines they wanted to create? They recognized it immediately.

And my wife actually co-created this class with Sun Neil. And she would give them storytelling exercises to try out, like calls with her mom. And they would come back to class, and they'd be like, I just had the greatest conversation with my mom I have ever had in my life. And it's just a reframe. It's just this idea of like, you know, you, you are in a mode. 'cause All human beings are, we just assume this is the way we communicate. But what if you tried it differently? And when you try it differently, it doesn't always work, but when it does, it feels like magic.

That was so well said. What an incredible story, too. All right. Next number.

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The Intersection of Improv and Business: Fuel for Creative Success with Kelly Leonard

Let's go to 11.

Number 11. Okay. You were once asked, okay, here we go. Let's talk about failures for a little longer. You were once asked, what should you do when your show gets a bad review? And you, Kelly said, frame it, hang it on the wall. I've even seen you've been known to share some of your own bad reviews. So, just talk a little bit more about how your failures have really helped fuel your creative success.

Kelly Leonard’s answer to “how your failures have really helped fuel your creative success”: 

Yeah. I fear this is bad advice for other people, but it was good for me. So here, if you are well-versed in improvisation, you are well-versed in failing because you fail most of the time. And by the way, folks, we all do, one of the scientists that we work with on our, our we had a thing called the Second Science Project at the University of Chicago, booth School of Business that we did for four years. And Nick Eley was one of the scientists we work with. And his research is all about how often we get it wrong. And in EPLI research, we probably get it wrong around 80, maybe if we're good 70% of the time or we get it wrong. Yeah. 80, 70% of the time, which means we're only getting it right 20 to 30% of the time.

Good batting average. Right?

Well, if you know that you are gonna be, or you should be pretty humble with regard to how you enter a room, how you communicate, what you think is coming outta this room because we're probably all talking past each other. And I often talk about this, and it's like it's not a surprise to the people I'm talking about. It's just that they don't think about it. Because honestly, if you thought about it too much, it would drive you crazy. I get that. But the idea of having a relationship with your failure, being comfortable with your failure, allows you to be more resilient and allows you to actually do a thing that, in our work, we talk about making mistakes work for you. How do I look at this, this potential failure? And, if I reframe it and look at it a little bit differently, it might seed an opportunity.

We say that you have to see all obstacles as gifts. So when we're improvising on stage, someone makes a mistake, it's like, that could be an opening. That could be a really intriguing place to take the story that we didn't think about before. But often, like you talked about in your story, you just freeze up. Mm-Hmm. Or you just stay the course and ignore the elephant in the room. It's like the guy is asleep, in improv on stage at Second City, you cannot ignore the guy asleep. In fact, the guy asleep is the best thing possible because it's gonna be funny. And, in fact, at that point, what do you have to lose? Right? They're asleep. So I think that, and we talk about an improv society, having fearless, I think that's maybe not quite the right word because you can't get rid of the fear.

But if you can sort of, like, play with the fear, recognize it's there, that becomes a really healthy way to navigate the kind of ambiguity that we deal with constantly, not just in business, but in our lives. I mean, it's like this, you know, it's not easy being a human, but here we are. So if we are here and we know this stuff's gonna be tough, and it's tough for us individually, it's tough for us in groups, we might as well have a kind of a curiosity walking in, walking into our, our rooms when we're trying to create stuff. And for us, I think at the theater, because we're a well-known comedy theater and a very successful comedy theater, when someone takes, like, just incredible shots at us, it is not unusual for us to be like, great, let's put it in the newspaper.

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The Intersection of Improv and Business: A Path to Growth with Kelly Leonard

Kelly Leonard’s advice: The response to that stuff is always like, people like, oh, that's a great way to like, deal with your bad press. Yeah. And it's not easy. It takes a while. But this is a key component of all of this, which is you don't go to a gym once, and you're done. So, in our field, the practices of being a good improviser, listening, being comfortable with fear, and being comfortable with discomfort are all practices that we have to lean into every single day, it never ends. I wish it did. I wish there were a place to coast. It just doesn't exist. But honestly, like, when you get in shape, and you recognize, like, oh, I just feel good. I wanna keep feeling good. Same deal. When you're in that sort of improv mindset,

That's really interesting. This is the first time I've ever connected this idea that it's not about being fearless, it's about having a relationship with your fear. I think so many times, you know, you've got a fearless girl, and yeah, I'm a fearless leader. And there's so much empowerment about being fearless, but it's not about that. It's actually quite the opposite. It's about understanding it, having a relationship with it, and positioning it to help you change and see things differently.

Because it's impossible.

Kelly Leonard shares his trick on how he controls his fear: 

You can't suddenly be afraid. That's right. I'll give you a trick, though. So I had this issue that I was dealing with in terms of a fear of heights. It got worse. And I was interviewing Annie Murphy Paul, who wrote an incredible book called The Extended Mind. And Annie's, she's a science researcher and author. And her contention in the book is that our metaphors for the human brain are bad. And we're just in the West in general, always thinking we can think our way out of things, and we're not as concentrated on the body. In fact, the body is a part of driving how we operate or behave as the mind is. In fact, she has done a lot of research in the book about things you can do with your body to get your body to say something to your mind, like, you don't need to be afraid at this moment. Mm-hmm. Okay. So one of the things that happens to me is if I'm driving on the highway and a giant truck goes by me, I tense up. I get a little scared. And so the trick I tried, and it really worked, was every time that would start to happen, I would smile. 'cause Guess what? It is very hard to feel afraid when you're smiling.

Kelly Leonard: And I gave this to my therapist, and she's like, I gave this to some other clients, and they loved it. It was just this little thing that they could do, but it didn't solve the problem forever. There are other things that we may have to do. But at that moment, that was a way for me just to get my body to relax a little bit. In the same way that science has shown us like, breathing exercises are maybe a really good thing to do if we're feeling anxious or nervous at the moment or we just wanna center ourselves. It's like putting your feet on the ground. Yes. Do some deep breaths. It doesn't need to be complicated.

It's complicated. I love that, and I'm going to try that. I will report back to you on, please do. Yes, that's great. All right. We get to pick another number.

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Kelly Leonard: The Intersection of Improv and Business — Keys to Effective Giving and Receiving

Let's go with number one.

Number one. Okay. So, feedback is a gift. I heard this through you in your book and through the training with Second City, and it has become one of the top seven core pillars of my business development philosophy. I actually tell everybody at the company within the first two weeks of meeting with me I explain feedback as a gift. I tell them what it means to me and how important it is. I try to create a team environment that also believes that because we have learned and grown so much when, we've gotten constructive and really positive feedback. So I'm curious, though, because some people's feedback is still uncomfortable, and they don't know how to give it, or they wrap it in so much positivity that it loses its meaning. So, can you give us any tips or tricks on giving and receiving feedback? So it's intended the way it needs to be. Yeah. And it can actually be used for good.

Kelly Leonard’s tips and tricks on giving and receiving feedback: 

I can tell a story about myself. Okay. Maybe that would help. I love stories. So, I didn't think I'd ever had a job review at Second City. I don't think I've ever been a performance review. I won't until this year.

And new artist. But this was mine. Actually, she wasn't even my boss any more. So my former boss, I now report particularly to the CEO, but he's been here six months, and he was outta town. And so our COO, my friend Presa Gilly, who I adore, who is brilliant and funny, and who is my dear friend and my boss and really an excellent boss. Like someone I really relied on in this position. So, I was supposed to have a job review, and I was getting weird about it in my head. And so I know enough about myself, and I know about enough about the science, then I was like, okay, I'm gonna talk to people about this because I just need to deflate this thing. And part of it is also going to be like going to my colleagues.

And I said, Hey, so I got this job, a performance review coming up, I'm in my head about it. And they all looked at me like, are you outta your mind? Like, why would you be worried? Like she's not even your boss anymore. It's like, your job title just changed. Like, everything about your position is like, you have absolutely nothing to worry about. And I'm like, ah. You're probably right. And then, if I'm worrying about this, what are you doing? And they're all worrying, and everyone has got the same thing. So I don't care how successful you are, and I know this is true, 'cause I know a ton of famous people, they imposter syndrome is real. We all think we're frauds. We all do. So the first thing is to get out of your head. It doesn't matter. You are gonna catastrophize this thing. And even if you're sitting in there and 99% of it is positive, you are gonna focus on the 1% that isn't. We all do it every single human. Can I swear on this podcast?

Yeah, go ahead. 

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Kelly Leonard: The Intersection of Improv and Business: The Power of Radical Candor

We're an advertising agency. Right? So here's a mantra from Second City, which is to take note. You don't have to agree with the note, you don't even have to like or follow the note. The note is an idea or a suggestion to help get you to a place that you want to go. So take the note and just shut up. So that is, that is a thing that we encourage here. And the other thing I have to think about is my friend Kim Scott, who wrote the book Radical Candor. Hmm. So, if you haven't read this book, it is an incredible primer on elements of feedback. So Kim has this grid that puts at one end of the spectrum the one you want to be on. It's just radical candor. The other end of it is obnoxious aggression.

That's when you're just being an. But in between, you're doing a couple of two things. One of those is called manipulative insincerity. So it's like, oh, you know, you're trying to cajole your way into whatever this conversation is. And the other is ruinous empathy, where you care so much you don't say a thing. Mm-Hmm. Which is probably what I was most guilty of when I was a boss here. And you're searching for radical candor. I love this person and care for them, I want to be truthful with them. And if they know I care for them, they're gonna take that, they're gonna understand that that's where I'm coming from. But you can't be radically candid with 'em unless you've set that bed of trust. So many people have heard of psychological safety, and Amy Edmondson, a Harvard psychologist.

She talks about it as part of Project Aristotle at Google, which was about finding the elements of the most successful teams. And they said psychological safety, the idea that I can sort of safely fail, but it's more than just that. And that doesn't get talked about very often. The scientist, Todd Cashton, has done research where he is like, it's not just that an individual feels safe to share a failure, it's also that diverse voices are respected and heard. And that really requires a kind of equity and openness to ideas that is not a norm in most organizations, even our own. So, the idea that someone with, you know, new intern might have an idea that's anathema to a lot of people with a lot of experience. But honestly, if you look at the research like experts, they don't do much better than amateurs and predict the future. And we're all trying to predict the future in some way. So maybe listen to everyone.

Listen to everyone. That's good advice. I remember my first interaction with radical candor. I was pretty young in my career. I had a great boss. And when you say trust, when I look back on it, I did trust him a lot. So it's probably why this worked. But I was in a rehearsal for a big presentation we were about to give, and I was very nervous, and I delivered my lines or whatever. And afterward, he pulled me aside, and he said, I'm just gonna give you one piece of feedback. He pro probably could have given me 50, but he gave me one mm-Hmm. And he said, you said 23 times.

I didn't know I said it once. Yeah. I would've come in the next day and probably said it 20 times had he not pointed it out. And I went home, and I rehearsed, and I was aware of what I was doing from that day forward. Yeah. It has been on my mind as an active part of something that I care about. And I didn't want that filler word to be part of my vocabulary and get in my way. Yeah. And I just remember how I fell and how grateful I was that everybody in the room was probably thinking it, but he was the only one who said it. And so, anytime I'm in a moment, the good and the bad, it's, if you have that trust, giving that feedback is so important.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Finding Meaning in Everyday Moments

I think you brought the word grateful. I think if you can make gratitude a guiding light of your day-to-day behavior, I often say meaning is made in moments. When we think of meaning, we think like these: the skies need to part. And that's not what's going on. How did I treat the person who was in front of me? What, what did I smile? Did I hold a door? Did I take a beat? You know, all, all these things. And that comes from sort of living with gratitude, which is hard. We get the beaten out of us. I mean, life is fair, and I've had tragedy, and other people have had a tragedy. But I also wake up in my comfortable bed next to my wife and the house I love.

My dog is downstairs, and the sun was out today, and I'm going to the Cubs game tomorrow. And yes, it's supposed to rain, but it's the Cubs, the season just started. And, like, I have so much to be grateful for. And, if we can concentrate on that, and I'm not talking about toxic positivity, which is a real thing. This is not about ignoring the real pains, the real problems. I have been in therapy for a long while for a lot of good reasons. So I'm working on that. And there are other things I do to sort of deal with that. But that also isn't to let me off the hook for trying to approach my life with this sort of ceaseless gratitude that I just think is going to make not just your day better but everyone's day better. And I remember Nick Eley when my wife Anne and I were first working on the project with him. We were walking across the campus at the University of Chicago, and he said something funny. He is like, Hey, if you're having a bad day, here's a little piece of science that we know. Do something nice for someone else. Hmm. It's, it's gonna make you feel better. And I'm like, really? That's it. What a win-win for everyone.

It's so true. When we were observing Mental Health Week at our company, one of the days, we gave everybody a hundred dollars, $50 to spend on themselves and $50 to gift to anybody you wanted. And the stories we got back, you know, sometimes it was a stranger.

A friend in need or a family member. You know, the whole line of people getting a free coffee. Mm-hmm. But it's what that triggers in your brain.

Right. It literally changes our physiology. Yeah. It literally changes how we experience this life that we're living. And here's the other thing, like, we have one life. I mean, you may believe in reincarnation. That's fine. Go for it. What's one chance, and do you want to spend that being a jerk? Like, do you wanna spend that so obsessed with money that you're looking past the person who's in front of you? It's like, I don't want to do that. And we know, you know, the, the study at Harvard, they've been doing for what, like 80 plus years studying what makes people happy over this incredible span of time. They've never done a study this big. It's relationships. It's about our relationships. And it doesn't mean that those relationships are always like hunky dory, but we have them. Yeah. We have relationships. There's a sense of trust, there's a sense of, of, of peace. Those people are wealthier, healthier, and they're happier.

Live longer!

Okay. Live longer.

Hmm. That's so good. I bet we could talk about it all day. All right, let's pick another one.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Boosting Confidence Through Improv

Let's go to 12.

The first question and the last question. Okay. So, the rules of improv can make you funnier. It's funny, the word funny how it's so associated with, with improv because Yeah. In business, you know, I often even said, I'm not funny. Like, I don't even know if I could do this. Right.

Right. Improvisation is not just about being funnier; it can also make you more confident. So I'd love for you to talk a little bit about that. Maybe share a story or explain how you've seen improv help boost people's confidence in the business world.

Kelly Leonard’s response to “How can improv make you more confident in the boardroom”: 

Okay, sure. Let me let me start. So my wife just sent in her second book to Northwestern Univer University Press. And the title of it is Funnier. So, my wife, Anna Libra, runs the first-ever BA in comedy writing performance at Columbia College. So you can get a degree in comedy. She's every parent's nightmare. But one of the things that, the reason the book is called Funnier is when she does open houses to talk about the program, she's at her booth or whatever, dads will come up, always dads, and they'll say, are you, you gonna make my son or my daughter funny? And she goes, I can't make them funny. I can make them funnier. The idea is that her knowledge of comedy and what she's gonna impart to these people will take whatever it is that they have and get that to be the best it can possibly be.

So she taught Tina Faye and she taught Amy Poer. They got a lot funnier 'cause they had that. But not everyone is going to be a professional comedian, but she will take it as, as far as you can possibly go, because you're, you're right. I'm not gonna get hired to be on stage at Second City. I'm a fairly funny human being, I think. But I remember that I ran a video star. So, so my, my in high school, like, it was like a senior year, and then into college, I ran a video store in Willette, Illinois. And then when I started working at Second City, and I had some success here, I remember the, the couple of fellows who own the video store took, took me out to dinner, and like, we're just, we never thought you were funny.

We just don't understand why you're at Second City. I'm like, I'm actually, what do you mean? I'm funny. They're like, just did not think I was funny at all. I'm like, all right, well, you know, it's different structures for different, different structures for everyone. So what's confidence, right? Sunil Gupta, who we mentioned earlier, has a really interesting thing in Backable that he talks about. And, he is not so much interested in charisma as he is in incompetence. Hmm. And he says, if you look at Steve Jobs on stage announcing the first iPod, he's not a good speaker. Mm-hmm. He, he, he's not that charismatic. What it is, he's, he believes in his product, and he is talking about it. And you understand that he believes in his product. If you look at Fred Rogers, Mr. Rogers Mm-Hmm. Fighting Congress to keep funding for PBS.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — The Power of Competence and Authenticity

Kelly Leonard discussed the power of competence and authenticity: 

He's also not a dynamic speaker. He just believes what he's saying. So, we respond to people who are competent and who understand their stuff. And they don't need Tony Robbins. Right. They don't need to have this incredible facade. It's like, what do you know? And can you talk to me about it? And be a again, and I think this sort of, this is where Western culture, movies, TV, mad Men, these things, these things are, are, they're, they're not real. They're stories. That's, that's not how it works. Mm-Hmm.  some of the most successful people I've met in my life are, you wouldn't be able to pick them out of a crowd. You know, they're not. Did you ever see the film Broadcast News? Do you know this? No. Oh, it's such a great film.

And I encourage everyone to see it because it still holds up. I watched it recently. But, the idea there is that Bill Hurt plays this young TV anchorman who's an idiot, but he's handsome, and he sounds good. And he starts to rise in the ranks. And it's really a battle for everyone to sort of like, but he doesn't know anything that he's talking about. And it's not real. And it's this, you know, this idea of like, yeah. If it sort of looks like a leader, and what does science, what does the data tell us about this? Which is men, white men over six feet are primarily the CEOs that we hire. Is there something about being a white man who's tall that qualifies you for anything except maybe being on the bench on a basketball team?

No, nothing. In fact, I would rather work with a woman in almost any regard. If I am looking for a new doctor, it is going to be a woman. 'cause I trust them more. Mm-hmm. I just do. And there's data to back me up on this. And if it's a woman of color, even better, that is someone who is going to look past me as a symbol of something and actually look at me as a human being of many facets because that's something that they've had to contend with their whole life as being looked past or looked as a single thing. So, I think that confidence is overrated. And I think instead, think about not so much passion as your purpose, your meaning, and your competence. Like, and, and this, this is actually not to be competence is really crucial because especially in areas, let's talk about DEI.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Lessons Learned on the Journey

Mm-hmm. When people feel really uncomfortable in this area, it's mostly 'cause they lack competence. So, generationally speaking, I have a lot of pronouns. I have a lot of love for older people who don't understand the pronoun thing. , I, I get it. It's hard. You don't understand. It's not always easy to see. And I think we need to give these people a little bit of grace to get there. Now they should try if they're just like, Nope, I'm not, it is like, all right, well, that's not, that's not being cool. You know, that, that, that's, you should, you should say someone's name correctly. See why that should be so hard. But recognize that there's context there. So this is just an idea of how you can gain competence, do the reading, ask the questions, and figure it out. You can get help. And all of that will make you more successful in whatever endeavor you're doing.

Very well said. All right. I think we have time to do another one. What do you think you game?

Yeah. let's go with eight.

Okay. Number eight. Okay. I'm so fascinated by your story. Our listeners might not know this, but you actually got your start washing dishes at Second City.

And then you went on to become the president of Theatricals. You were responsible for hiring Tina Fey, Stephen Colbert, Amy Poer, and Steve Corll. All along the process, I find that not a lot of people work their way up from the bottom through an organization like this. What would you say you learned maybe in those early days that helped prepare you for what you're doing now?

Dumb luck. Maybe, no, it's maybe more than that. So, yes. My first gig out of college was as a dishwasher. The other guy who got hired that week was John Favreau, the film director. Wow. And we both had mullets, and there is photographic evidence in my wife's office.

That second city I need, I need evidence.

Next time you're in Chicago, we'll walk you up. You'll Okay. You'll see a really wickedly bad mullet and maybe an ear cuff. I'm, I'm not promising, but there, that, that existed at the time. Yeah. I wanted to be a playwright. And when I had done informational interviews around town, the suggestion was, if you wanna work in theater, work in a theater, whether it's tearing tickets or whatever you're doing. And the job I got here was washing dishes, and it was terrible. Mm-hmm. But you got to see the shows and it sort of was incredible. I didn't know that Second City was created through improvisation. I just knew it was funny. And I'd come here a bunch when I was in the kitchen, Mike Myers, Bonnie Hunt, and Jane Lynch were all in the professional company. Chris Farley had just been hired by the touring company and was constantly getting into trouble for breaking stuff. So, it was an incredibly magical time. What did I do? I listened, I showed up early, and I worked hard.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Finding Opportunity in Disorder

I was curious about everything with regard to the business. I've just always been that way. My first job was at the Jewel Food Store in the Plaza de Lago in Wilma Wilmette, Illinois. And when I started, I took about a, I was a bagger. I was there for about a week, and it dawned on me. I asked one of the managers, and I said that this felt like chaos barely contained. Like, like, they're like, and, and they're like, absolutely. I have yet to work in an organization that anyone would describe as functional. And I have yet to meet any individual who would say that they worked in a place that was purely functional. So, Ashley, I will turn this on you. Have you worked in a place where it wasn't just barely contained chaos?

No. It is everywhere. Yeah, even I own a company now, and I would say most of us would be even worse.

Right. Did anyone teach you this? Did anyone even suggest this in the least? No. That, no. So this is a lie among the many lies that we, whether overt or covert, who knows that they don't teach you, which is we're all just making this up. And if we're all just making this up, you can have two responses. You can be like, I am going back to bed and never getting up. Or you can laugh because it's really funny. And then recognize like, if this is barely contained chaos, I have loads scads of opportunity walking in the door to make it less chaotic. So I eventually got out of the kitchen. I hosted the room, I worked in the box office. I recognized that we were losing a bunch of phone calls. 'cause We were so busy at Second City.

And by the way, at this point, there were no computers. We were a cash-only business. So it was just some phones. And I said I think that there's probably like sequencing machines of some sort. I'm not a technical person, but I just sort of thought that this must exist where people could be put on hold or leave a message in some way that's not an answering machine. 'cause That's what we had an answering machine that could hold like 10 messages on tape. So yes, exactly on tape, And I was convinced that it was a choice cylinder, the producer at the time that we should research. When I came back, we put in a phone sequence sequencing machine, and we discovered that we were losing about 160 calls a day. And we put a dollar sign to that, and we're like, well, this is a no-brainer.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Navigating Career Growth and Business Success

And then we started losing fewer phone calls, and business went up, and that's just my approach, which was always to at least ask the question, like, has anyone thought of this? Because maybe they haven't. And if they had, no one's gonna be like, shut up. And if they are, work someplace else. Hmm. So, so I, I was lucky I worked at a place where like, yeah, no, we haven't done this. And hey, had anyone thought about making a brochure for the company? No. All right. What if we do this? And we did. So I, I think, and then, and then right place, right time. I can't say that at 26 years old, which is when I was hired to be the producer of Second City in 1992, I was anyway qualified. But I think they knew I would work hard, and I did. And I got better at the job. And my friend Anne, who ran the box office then who is now my wife Anne, I asked her for advice before I started becoming the producer of Second City. And her one piece of advice was when you make a mistake, say you're sorry.

I've held on to that to this day, and I think it's held me, held me well.

That's great. That is, that's great advice for anybody just starting out in their career. And then I think it's also good advice for people who have been in their career for a long time. I think there's a lot that you can experience and learn about, like seeing all facets of the business. I think some of the best CEOs have spent time in all parts of the business. Oh, yeah. Yeah. And we, because we don't really understand the struggles of the kitchen or of That's right. The box office or of the comedians on stage, the cleaning crew. And you can really only experience it once you've lived it.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Balancing Frontline Engagement and Strategic Vision

Yeah. Ron Heifetz, who's a Harvard professor who teaches leadership, his metaphor for this is that you need great leaders. Both basically go back and forth between the dance floor and the balcony. So it's moving. For example, if your office as the leader of the business is the farthest away from the customer, you've made a grave mistake. So this idea of, like, and it's not just living on the front lines either because you do that too much and you're not gonna see the big picture. So how do you focus: zoom in, zoom out, zoom in, zoom out? And that's not a natural, again, not a natural thing for human beings to do. So you're gonna have to basically create somewhat Richard that calls choice architecture, design your experiences so that you can have authentic frontline observations, conversations, and then also getaway.

How can I get back and now just see this thing from 2000 feet that will give me another idea? And that involves asking a lot of questions. And, and, and, and also really speaks to the world we live in, which I think when I was certainly growing up, we still live very much in what was a top-down sort of leadership model. It's not the way the world is now. I mean, it's, it's decentralized, you know, so you gotta know what's going on all around you, not just what the richest guy at the top says is, is happening. You've gotta see if you've gotta see around corners because, you know, I was fooling around with chat GPT for this week, and it writes a better press release than I have ever written in my life. And I'm a good writer.

That's great. That's a great comment to end on. I am so grateful for your time. I think we should do part two if you're always game. Sure, of course.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

Kelly Leonard: The Intersection of Improv and Business — Exploring the World of Improv and More

There are some equally meaty questions behind the ones we didn't get to today that I would love your perspective on. How can our listeners reach you?

So you can find me on LinkedIn and Twitter for now, in the second city. We'll see how this blue checkmark thing is gonna go. But I'm actually getting a lot of people, I do a lot of public speaking. I reference a lot of books. So I often, after my talks, I go to LinkedIn and list the books I  talk about, and that's become kind of a cool thing where we're continuing the conversation. So I think more and more that seems to be a good place as these other social media sites may. They're having some issues. 

I have to deal with that every day.

I know, we all do.

We will also be sure to link to all of the books you mentioned in today's podcast.

Great. Thanks for having me, Ashley.

Absolutely. Thank you so much, much. Hello everyone. Welcome to Question Everything, a podcast all about learning from the successes and the failures of those who dared to question everything Well. This podcast is part interview, part therapy, and part prices. Right? We even have our own game board stacked with questions that'll make even the most successful CMOs Sweat. I'm your host, Ashley Walters, chief Development Officer and partner at Curiosity. So

There needs to be a transition there. Curiosity is one of the biggest business goals. Do you think that's right? Or do I need to say something else on today's episode?

So, on this episode, we dive deep into the world of improv.

Do you think that's good enough?

Yeah. We're starting to, we kind of did that here.

What if we like to get rid of this: Copy it and paste it right after. Paste it right there. On today's episode, I sit down with Kelly Leonard, a longtime creative executive at the Second City, bestselling author of Yes and, and host of Getting to Yes and podcast. In this episode, we dive deep into, dive deep into the world of improv. In today's episode, I sit down with Kelly Leonard, a longtime creative executive. I should stop recording this. Hello everyone. Welcome to Question Everything, a podcast all about learning from the successes and failures of those who dared to question everything. This podcast is part interview, part therapy, and part prices, right? We even have our own game boards stacked with questions that'll make even the most successful CMOs Sweat. I'm your host, Ashley Walters, chief Development Officer and partner at Curiosity. Today, I sit down with Kelly Leonard, a longtime creative executive at the Second City, bestselling author of Yes and, and host of Getting to Yes and Podcast.

Learn more about the intersection of improv and business by nurturing these 3 improv tips for hugely inspired teams

The Intersection of Improv and Business: Bridging Comedy and Business with Kelly Leonard

Hello everyone. Welcome to Question Everything, a podcast all about learning from the successes and the failures of those who dared to question everything Well. This podcast is part interview, part therapy, and part prices, right? We even have our own game boards stacked with questions that'll make even the most successful CMOs sweat. I'm your host, Ashley. Walters is the Chief Development Officer and partner at Curiosity. Today, I sit down with Kelly Leonard, a longtime creative executive at the Second City and bestselling author of Yes and, and host of Getting to Yes and podcast. We dive deep into the world of improv. Did you know that some of the biggest business schools in the country incorporate improv techniques into their teachings? In fact, many top CEOs have studied the art of improv. Kelly's advice for us is so meaningful we're breaking it into two episodes. A few of my favorite topics from today's episode are why having a relationship with your fear is more important than being fearless. How a bad review creates tremendous opportunity and why. The secret to connecting with humans isn't talking about your successes. It's actually about sharing your fiascos. So whether you wanna be a bit funnier or more confident in the boardroom, tune in for an incredible inside. Look into the techniques and tools that bridge comedy and business.

Hello everyone. Welcome to Question Everything, a podcast all about learning from the successes and the failures of those who dared to. Well, question everything. This podcast is part interview, part therapy, and part prices, right? We even have our own game board stacked with questions that'll make even the most successful CMOs sweat. I'm your host, Ashley Walters, chief Development Officer and partner at Curiosity. Today I sit down with Kelly Leonard, a longtime creative executive at the Second City. He's also a bestselling author of Yes and the host of Getting To Yes and podcast. We dive deep into the world of improv. Did you know that some of the biggest business schools in the country incorporate improv techniques into their teachings? In fact, many of the top CEOs have studied the art of improv. Kelly Leonard's advice for us is so meaningful we couldn't fit it into just one episode. A few of my favorite topics from today are why having a relationship with your fear is more important than being fearless. How a bad review creates tremendous opportunity. And why is this secret to connecting with humans not talking about your successes? It's actually sharing your fiascos. Whether you wanna be a bit funnier or more confident in the boardroom, tune in for part one of an incredible inside look into the techniques and tools that bridge comedy and business.