Mastering the “Yes, and” Mentality: Full Episode Transcript - Kelly Leonard Second City Introduction:

Hello, everyone, and welcome to Question Everything, a podcast that's all about learning from the successes and failures of those who dared to question everything well. This podcast is part interview, part therapy, and even a little Price is Right. We have our own game board stacked with questions that'll make even the most successful CMOs totally sweat. I'm your host, Ashley Walters, chief Development Officer, and partner here at Curiosity. Now, back by Popular Demand. Today I sit down again with Kelly Leonard of the Second City. He's also the author of the book. Yes. And for those of you who missed the first episode, stop what you're doing, go back and listen to that, and then come back over because there is no other podcast that's gonna talk about juggling monkeys and lead you through a live improv exercise that you can do at your home or even at your office. I was totally sweating On today's episode, you're gonna learn that if you wanna raise in 2023, take a page from Ted Lasso and work on your soft skills. We'll also talk about why saying yes is just like saying no with the top hat. And then, if you have an Amy Poller on your team, find a way to use them. Hello, welcome to Question Everything. Today is a very special episode, one of a kind that has never been done before. And that's because I am joined again by our guest, Kelly Leonard. Welcome, Kelly.

Ashley, it's so great to be with you again. Thanks for having me back.

Oh my gosh, I'm so excited. So Kelly is a longtime creative executive at the Second City, and on part one of our podcast, which, if you haven't listened to, definitely do that now, he dropped some serious knowledge about improv in business. We talked about why we shouldn't fear failure and how leaders can be more vulnerable, and it was so inspiring that we decided today we are going to clear the board. That's right. So today, Kelly is going to answer the final six questions on our game board, and I promise you, Kelly, there are some spicy ones in here.

Excellent. Let's do it.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Exploring the Improvised Nature of Language

This is only for you. I know it's only been a few weeks since we last Sat down, but is there anything new with you? I'm sure there is.

Oh, a ton. Yeah. I'm taping, you know, I host a podcast called Getting Yes. And, today I am taping an episode with Nick Chatter and Morton Christensen, who are two scientists who have a new book called The Language Game. And it is their contention that language is improvised. And so it's this whole book on prior linguistic theory, which was maybe sort of like language is this thing that's all sort of innate inside of us. And then, it comes to us, which kind of makes no sense when you live in a world with like 800 languages Yeah. , which are all completely different. Their point is that when you're young, the way you get good at language is by playing and practicing with others. Which I love 'cause this is the basis of my entire life's work.

But it is also very interesting when you think about communication, when we're good at it and when we're not good at it, and they sort of blow up all these sorts of previous theories. And basically, they say it's almost like a game of charades, too, when you're talking to people. Cause you don't just rely on words. If we did that, we'd have a lot of trouble.  We have all kinds of contexts and stories together. We're assuming a lot of things based on whether we maybe watch the news or what the weather is like outside. Which means that, you know, there's more going on than just the language we happen to be speaking in.

Fascinating. And that's gonna go live when?

That'll go live in about six, seven weeks. Awesome.

I can't wait for it.

Good for you. Okay. So are you ready for this?

Yeah, let's do it. I know you are. Okay. Let's see.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Power of Improv and Soft Skills

What number are you gonna pick First?

Let's go 10.

Number 10. All right. You recently penned an article on the reasons why taking a weekly improv class will get you a hefty bonus in 2023. We all need more money in our life. Yeah. Tell me what you mean.

Kelly Leonard Second City response on why taking a weekly improv class will get you a hefty bonus in 2023: 

Well, this was my clickbait moment, right? Here's the deal. You know, when we talk about people who are successful at work, it's not simply people who are vocationally good. Certainly, that can be important. You know how to code, you know how to write, you know how to do all these different things. That stuff can usually be taught to most human beings. People who succeed are successful in what we call soft skills. And that's a terrible term. Seth Godin has a new book that's coming out soon, and he calls, he wants to call soft skills real skills. Cause they're the real hard skills. So this is, are you a good team member? Do you come up with interesting ideas? How do you show up in a room?

And I don't know about you, but when I went to school, I wasn't taught any of those things. I might have learned some of that when I worked on a play or when I was on my soccer team. A little bit about sort of being a good team member or good cast member, that sort of thing. But improvisation specifically is working on all those skills. And it's not just scrimmaging. It's not just about getting on stage, and hey, we're just gonna make a bunch of stuff up and then, you know, draw your own conclusions. That's not it. We break it down. We look at, okay, what is it? And we didn't, I don't think we talked about this the first time, which is funny. We didn't really talk about yes and no. And, one of the things, that's why that's such a sticky concept and, and wasn't the original title of the book.

When we pitched to Harper Collins on a book about improv, our original title was The Revolution Will be Improvised. Which we all thought was cool and catchy. But then when we led the sales team at Harper Collins through an improv workshop, just to sort of, like, get them to experience what it is when they did the yes and exercise, they're like, that's it. That needs to be the title. So what we know from science, and in particular from behavioral economics, is that people's default position is to say no or do nothing. That's what human beings are, we're not rational actors. Our default is, like, I'd rather sit on the couch. So, and I think we all know from personal experience, so what Yes. And it's a kind of a nudge for you not to do that. And so if it's our default position, we need practice in saying “Yes, and”.

And so the exercise is really simple. We pair up two people, person A and person B, and we say, Hey, it's a year from now. We've had such an amazing day together. We're gonna have a reunion person. A: you're gonna pitch your reunion to person B. Person B, your job is to say no to every idea and as many different ways as possible go. And we have them do for doing that for about a minute. And it feels terrible unless you're a masochist. And then we say switch places. And person B pitches their ideas. And we say to person A, you're gonna respond yes. But to every idea. What's funny about this is when we debrief that section, usually half the room thinks it was better, and half the room thinks it's worse. And the people who think it's better, they heard a yes, they're ignoring the but, and the reality is yes, but is like no with a top hat, you are getting a no.

And it's a very normal way of communicating at work. And then the third pillar is where we say, right, pitch your idea. And everyone, yes, and every idea agrees to the idea and builds upon it, agrees and builds. And we say, don't worry about budget, don't worry about the laws of physics. You could be having sushi on the moon with Led Zeppelin. It's fine. And what we know at Second City is we apply this creatively in the process of creating a show. So if we if we're writing a show, usually over a 10 week period, the first three weeks, all yes. And give me every idea. I don't care how dumb it is. I don't care how wild it seems, we're gonna put it up, and we're gonna try it because nothing that was truly innovative, you know, like, looked like it would make sense; otherwise, it wouldn't be innovative.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Saying Yes to Innovation

That's the point of innovation. So what we know, in addition to human beings saying no, we're doing nothing, is that we are also deeply involved. The reason we do this is we're deeply involved in the judgment of self and others. And when you're wanna be creative, and when you want to improvise, you can be neither of those things. You cannot be in judgment of self and not in judgment of others. And once we teach people that, that is a practice, right? This is the important thing. It's not just like, it's not an idea. I mean, it is, but more importantly, it's a practice so that you can get your body feeling that way. So that, and look, as a parent, I mean, we are the kings and queens of no. And the way I've utilized that as a parent, yes.

And has been really powerful with my kids. 'cause I don't wanna be saying no all the time, and I'm just way more creative when I say yes. And when I'm like, and I remember I did this with my daughter Nora. She wanted a raise in her allowance. And I'm like, you know, normally like, no, there's nothing you've done that deserved hers, a raise. But I said yes. And if you can show us and explain to us in a, in a sort of full detail why you deserve that, you'll get it. That night, she prepared a PowerPoint presentation, which was just a series of construction papers that she had put together. She grabbed one of my suit coats and one of my ties and sort of crudely put it on and went through this amazing, like, just convincing speech about how she deserved a race. She was in her allowance, and she got it. I mean, I was like, Hey, if you're gonna be that creative, that's a huge yes. And right there.

Oh, I love that. I'm a mom of three little girls, and I try to instill some of that into them, especially my 7-year-old. I really hope you took a picture or a video of that.

No, but I have it in my head, which is the most important thing.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Power of Yes and Confidence

Yes, you do. Okay. I love this idea. Focusing more on soft skills development, leaders and managers recognize that, right? And when they see that in somebody, that's the bonus potential. That's the raised potential. That's the next level that we're all looking for.

Yeah. It's again, you know the details of, look, I went to a good high school, and they taught me how to write a five-paragraph essay. It's important that, like, the five-paragraph essay, is very important in terms terms of a certain kind of communication. But that's not what, like, got me an award. That's not what got me a book contract. The thing that got me a book contract was going in the room and having this editor connect with me. And they're maybe connecting with ideas, but you don't connect with ideas if you don't connect with me. That's a huge thing. I know we talked in, in the first episode, about my friend Sunil Gupta and about this idea of how you make yourself backable. And that's part of it is, like, you gotta get people to believe in you.

And so if they do, they're gonna wanna work with you. And I think for, and I know this for, for myself in terms of leading teams and promoting people, who shows up and is ready to play? And not just sort of ready to play is, is occasionally fearless. Those sorts of things. Again, not a thing that's taught in business school, right? It's not a thing that's taught in many schools. So, where do you pick this up? Of course, some people are somewhat naturally gifted, but I would even say those people, naturally gifted, probably have places where, throughout their life, they've been able to practice what it means to take a shot and get turned down and then go back and do it again. And then that gets accepted because it's really hard.

You get turned down. You know, when you get no when we say no to ideas, we often are saying no to people. At least, that's how they feel it. Whether you know that or whether you believe that or not, it's like, you know, performance reviews, and we all hate them. And any tiny little criticism is the thing you're gonna hang your hat on for the rest of the day, even if 95% of the performance review review is good. So when you understand how human beings tick and that most of us, you know, do want to play with people who play well with others, I think you're going to really put yourself in a position to get the big bucks. Yeah. If you focus on that part of your career.

And you know, we work in a creative agency, I mean, all creative agencies. Listen, if you're not having these, yes. And moments in your brainstorming as you're ideating new client campaigns, start doing them. Now. I've been a part of it a few, and it is really, really powerful. I oftentimes will hear a lot of, like, young creatives or young executives apologize for their idea, or they'll say, this might be a bad idea, but let's shed that, right? Yeah. Like stepping into our confidence. And when you give them that authority, they know they're not gonna get a no or a but.

I think you celebrate your bad idea. There's a director, MC Napier, I don't think we talked about this before. M has been directed at Second City for a long time, and he recognizes that it doesn't matter how good you are or how experienced you know; we all have imposter syndrome, and he'll be working with the Second City main stage cast. These will be, at any given time, the six specs best improvisers in the world, bar none. And he knows they even self-censor themselves. So he'll do a thing during rehearsals where he'll say, Hey, it's, I'm gonna do Taboo Day. And Taboo Day is where you have to bring in three ideas that there's no way in hell Second City will ever put on the stage. And, and so that is the rule. So it's too expensive, it's too offensive, it's too problematic, whatever. And invariably, you know, 5, 6, 7 pieces out of that day end up in the show simply because people, I didn't think you would even let me say that. It's like, say it. And the thing is, we're saying this to individuals, but what we really are saying this to as leaders. Leaders have to make space for people to bring in their terrible ideas. That might be brilliant. Mm.

Love that. Love that.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality —  Embracing Selfless Curiosity for Success

All right, let's go back to the game board. Okay.

Let's go two.

Number two, okay. So, as you know, well, we're, we're very passionate about curiosity. It's in our name. And we've read that selfless curiosity is a core philosophy of yours. So, what does selfless curiosity mean? And in your opinion, why is curiosity so important for a successful show or business?

Kelly Leonard Second City response on what selfless curiosity means: 

Well, okay, selfless curiosity relates to a phrase, and I don't know where this is, I don't know who actually said this first. I don't think it was me. But we talk about the need to replace blame with curiosity. My friend Liz joined Sandberg, who's a longtime teacher, actress improviser at Second City, she was doing a standup set once, and a guy was heckling her, and she decided, instead of coming back with a zinger to nail this human, which is an appropriate response at certain times, she instead was like, I'm curious why you are actually saying this stuff to me from the audience. And this guy was caught so off guard 'cause he could not explain it. And they actually ended up having kind of a lovely back-and-forth that ended up being funny. And her point was that, all right, that worked for me on stage, but it won't work every single time.

But what if we took that attitude when we go into our various rooms where we are gonna make a lot of assumptions about the things that are being said? As we were talking earlier about the language game book and, through other studies that we've worked on the chances are that of us understanding everything that's happening in a room is like nil. Like, it's like, it's not happening. We understand a bit; we get some of it, but we don't know what just happened to this person before they came in. We don't know if they're using a word in a certain way that we are, you know, using it in a different way. So maintaining a level of curiosity as opposed to everything else. I mean, everything else, just this. Like, if you're in this curious state, you're gonna ask questions.

Kelly Leonard Second City continuation response: 

You're, you're not gonna be judgmental because you can't be, you're gonna be like, I'm curious. I'm not judgmental, I'm curious. Tell me more. And this is the other thing about human beings is they desire to be seen. When we first started working with scientists at the University of Chicago, my friend Heather and I were sitting at a table, and we were talking about our work. We talked about the need to be focused. So it's really important that you're always focusing on your partner. And she's like, oh, I just read a paper that kind of takes that maybe even a layer deeper. And it was by William Swan, who's a professor in Texas, and he has, a thing called self-verification theory. Okay. And I was so blown away when she talked about this.

Kelly Leonard Second City continuation response: 

She said I think we think that we as human beings want to be seen as our best selves, our prettiest selves, our smarter selves. Swan says that's not true. The studies he's done have shown us that we desire to be seen as we see ourselves. But we're human beings. We're tricky. We won't tell people what that is. So, the idea here is if I see myself as clumsy, I want you to see me as clumsy. So you won't throw me a ball, but I'm not gonna tell you. And I'm like, oh. So that requires on behalf of the other sort of per-part partner in this communication, this conversation, whatever it is, of getting deeper, because this person isn't gonna tell you. So, how do I ask more questions? How do I get to what they care about?

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Unlocking Connection Through Everyday Details

You do that by asking more questions, but you also do that by getting people to reveal even the most seemingly mundane details about who they are. And when we learned about this research, we were asked to lead an executive education program, and Heather was like, could you turn this into an exercise, you know, that would teach people how to sort of, you know, talk about themselves in ways that can get other people to understand them. So, understanding that people are reluctant to self-disclose is another thing my wife Anne helped create, this exercise called Universal Unique. And when we pair up two people, we pick a mundane task. And the one that we always laugh about is grocery shopping. So the first person just describes how human beings grocery shop, you know, I get in the car, I go to the store, I put stuff in my, you know, a basket, whatever.

They do that for about a minute. And then we say, okay, now take a beat and think about how you personally grocery shop. Okay, go. And guess what? We're all freaks. We all do the weirdest thing. And people are laughing. And after we debrief this with, with, with folks who are like, well, what was different? And they're like, I learned so much about that human being just when they talked about how they actually grocery shop. And it's true. So, we don't need to self-disclose the greatest fears, passions, grief, and trauma. Right. Though sometimes we should. But if we just talk about the way we live our everyday lives, that's pretty entertaining. There's a reason we all like Seinfeld. It was talked about everyday activity. And guess what? It's funny and interesting 'cause human beings are weirdos. And that's a great place to connect sort of. And we've talked before about authenticity. That's how you get to authenticity. And it's not you trying to shine yourself up, like you don't make any mistakes or like everything's fine. It's like no one wants that. We talked about the fiascos. Give me your fiasco. Gimme your struggle. Give me your pain. You know, do you have a dog? Do you have a cat? Knowing these things will help me understand you. And then vice versa as well.

That's a great exercise. I think we should do that with our teams more, too. You know, I'm thinking about all the people I work with on a daily basis, and I've never asked them that. Yeah. Or simple questions like that. And it's so true what you can learn, and it's relatable, right?

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The New Era of Marketing and Connection

We all do it in theory. And if we don't, that's funny. And also I would say this as people who are in marketing or advertising or promotion or any of those things or require moving other individuals to do things, whether you're talking about influence, whether you're talking about any of those things, this idea of getting them to tell you where they're at, what they love, what they don't love, those sorts of things. All of that is incredible. You know Intel is incredible data. And this is the interesting thing from when I was a young person until fairly recently, 15, 20 years, you know, that business, the advertising marketing business, was all about throwing messages out, throwing messages out. And now, of course, it's like there are no monologues. It is dialogues 24 and 7, whether we like it or not. And often, it's not always fun.  the comments section of your post is not always fun, but it's the reality of the world we live in. So you might as well sort of dig in and make it fun and interesting. And if you open up, I'm telling you, other people open up as well.

That's why a lot of brands turn the comments off. They don't wanna hear it.

Yeah. That's not smart, I don't think that's a smart idea. And I think I don't envy anyone because someone tweets a certain thing; there's gonna be people shooting at your beer can. No one enjoys that. But, the reality is, you know, you can no longer exist in Switzerland. With this stuff. I mean, that is a lesson we've learned over and over and over again, this is the funny thing for me. Like, I work at Second City, it is a comedy theater that was started by beatniks and then hippies in the middle of Chicago, a liberal city. We know, like, you do not have to guess, you know, what the politics might be if the performers are up there. And most of the time, that's no problem.

And in fact, I prefer, frankly, conservative crowds to liberal crowds in terms of, like, sense of humor. That's just me. But every once in a while, when the culture war starts hitting, and we're in one of those places now, people come in and they're outraged of like, what are you doing? Like, you know, you should know where you are. You know, I'm not gonna go to Dallas on a street corner and, like, be upset because someone might have a conservative view. I mean, like, know where you are. Not that I don't know why I'm picking on Dallas and Houston. Let's pick up Houston

Excellent. All right. We've got four.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — A Leader's Guide to Harnessing Greatness

 All right, let's do nine.

Number nine. That's my favorite number. Okay. You said one of your biggest regrets is not using Amy Puller's talent to the fullest while you had the chance. What's your advice to leaders when they have someone that good on their team?

Kelly Leonard Second City advice to leaders when they have someone that good in their team:

All right. I'm of two minds. So the fir the first is gonna be what I'm saying here, which is when you have great people, you know, find a way to use them, that that's just, you know, they're not gonna be there forever. One of the things that is cool about Second City is that I never would have understood this either in an artistic way or in a business way until I lived it, which is we train up amazing talent to leave. So none of them stay. Amy was always gonna leave. Tina Faye left, and Stephen Colbert left. Jason ADEs left Keek, and Michael Keye left. They, they all do. What that does is a couple of cool things. One is it makes space for the next generation to come in, so you're not sort of like stopping. And the other thing it does is it creates what people in, in the business world might call brand ambassadors, which is Amy, even though she, you know, didn't end up on, on a resident stage.

Kelly Leonard Second City continuation response: She was in the touring company. I should have put her in a resident stage sooner. But she still goes on, you know, talk shows and talks about her work at Second City and how important it was to her. So all that's good. That being said, you know, do not waste a great talent. Find a place for them. And I think too often, you know, look, we don't wanna rock the boat, you know, we let the person stay a little longer because it's like easier than having the difficult conversation, but you're not doing them any favors. You know, you're, you're just not if their time is done at your place, and I'll tell you what, they probably know it too. You're just dragging out the inevitable. And it is rare for me. I can count on one hand, and I've fired a lot of people. I can, on the one hand, the amount of people who were still mad about that. Most people found the new thing. It was cool. And then we have a funny story about how I fired them, that we talk about when we get together.

Is there a lesson there?

No. Okay. The lesson there is to be really human. You know, when you are with people, if you do have to fire them, do it in the most empathetic way possible. You don't do it in public, you do it in private. You figure out your timing so that it's a place where like, hey if you're, you're not leaving right away. You know, you have the night off, you have the day that you don't have to come in tomorrow, whatever. I get it. You know, like you're, it's gonna be emotional. It's okay for it to be emotional, and you shouldn't be upset if they're emotional. You should be like, cool with that. Have Kleenex ready, whatever, you know, be human. And then, they're not right for a gig, but they might be right for something else.

Like, Hey, there's another opportunity here. There are all kinds of things you can think about to help your people when they may be no longer gonna be your people. And if you do that, you're just helping the ecosystem writ large. 'cause Guess what? People talk to each other, and they'll be like, Hey, was that a good place to work? I know you, like, you, you got to let go or whatever. And, and if a person can be like, I gotta let go. But yeah, it is a good place to work. That speaks volumes significantly. It goes the other way. So when people are like, no, it's a toxic work environment, like, oh, I'm not touching that. I wouldn't even apply to go to this place if I heard that. I got to interview Melissa Daimler, who is an HR person, she had a terrific book on culture. She also happened to be the HR director at WeWork.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Why Surrounding Yourself with Greatness is Key to Success

Wow. And she had plenty of Adam Newman stories of him not wearing his shoes and asking her if she had plans on being pregnant. To me, these are things that would be being, Hey, see you later, And she, and she didn't stay long, but it was, you know, and that's why she wrote this book about culture because she saw how terrible it was at WeWork and, under the guise, of course, that it was the opposite, creating some sort of vision, you know, for the future. I mean, and I know this guy just got another, you know, whatever incredible amount of seed funding to do it again. So, you know, there is no justice, and that's fair. That's the other problem. But it doesn't matter. You should ethically and morally do what you think is right and do the right thing. It's gonna help you sleep at night.

Yeah. On the Amy Poer side, like when you have somebody that's that great, you know, like, I think as leaders, some, I've been on both sides of this where I've seen leaders like really lean into that and like, create opportunity and open doors. Then, others are a little timid, afraid, and unsure, and they start to think about their job and their job security. What if they could take my job?

Oh, that's bad. You never want to be the smartest one in the room. Never. You should always hire people who have more expertise than you do. All of that will make you look good to your bosses. And if it doesn't, you are in the wrong place.

I couldn't agree more. I have always thought and been taught that you should hire somebody who could take your job. Yeah. And if you surround yourself with people who are that good, everybody rises, right? Yep.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Co-Creation in Business

Love it. We've got some Amy pullers at our agency, that's for sure. All raises. You've got three more.

Okay. let's do three.

Okay. One of my favorite lines is, bring a brick, not a cathedral. We actually have a process at our company called Bring a Brick, not a cathedral. I've seen it. Excellent. It just completely transforms people's mindsets when they come into a meeting. So, what can business leaders learn from not trying to solve it all? Maybe explain, bring a brick, and Yeah. Talk about its importance.

Kelly Leonard Second City response on what business leaders can learn from not trying to solve it all: 

So when we talk about that at the heart of Yes. And is this idea that we're gonna co-create something together? That it is never, we have an unfortunate thing. And it's not just our country, it exists in other cultures as well, commonly referred to as the Great Man theory. This idea that these great men did it all that Steve Jobs guess what? He didn't invent the iPod. I started IBM; they were idiots. They didn't do it. I mean, he's a great marketer. He was a great design thinker. All those things. I'm not trying to knock down Steve Jobs. He didn't do it alone. And neither did Thomas Edison had like a hundred people in a workshop doing these inventions. So, this theory is wrong. The way things get done and made is by lots of different hands touching up. And my friend Mike Norton at Harvard has a concept called the Ikea effect. Okay. And the Ikea effect actually says that we put a much greater value on things that we had a hand in creating. So at Second City, when you're giving a suggestion for the improv set, and then we use it and put in a scene, like, you feel way good. Cause you helped make the show that night. And even like, the stuff with Ikea, I mean, this is not true for me. I've never put together anything I've put a lot together.

Kelly Leonard Second City continuation response: 

Yeah. But this idea, hey, that's why a lot of people like it. They felt like I made this even though I don't know if you made it. You followed some instructions, and that's fine. But those sorts of things. So, at the heart of co-creation is not walking in with a solution. It's walking in with part of the solution and then being willing to hear what someone else's part is. I have a friend who's working on a show right now, and she's got an improv background, but one of the people that she's working with doesn't, and they keep coming in with these sort of, like, full ideas, fully baked and get so upset when other people change them. And it's like, yeah, this is not what we're doing here. We're not just doing your monologue, we are creating together.

And when we do that, I mean, honestly, there's a great phrase: your team is only as good as its weakest member. And we actually don't like that we switch it when we say your team is only as good as its ability to compensate for its weakest member. Because at one point, we are gonna be the weakest member. So, if part of this, the thing that we're doing involves math on the fly, I am not your person. But if it involves obscure eighties rock music trivia, I'm there. I got you. I'll make the aha reference. I know some Duran Duran. So, understand that this diversity of viewpoints all coming together is a huge part of it. And that's at the heart of that idea.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Juggling Monkey Approach to Progress

It's interesting. I was talking to Annie Duke, who has a great book out called Quit. Part of it that she talks about is like the Great Man theory. We also have a cultural trope that quitting is bad. Right? It isn't like, even like the term, like it's like's gotta be bad that all the time can't quit. Okay. But quitting smoking's good, right? Right. So, wait a second. But that quitting and we have to quit. We have to quit a lot of things to then do other things. We quit constantly. So we just have this sort of like, weird trope. This is why words are important, by the way. Yeah. I know this is a weird thing to say, but we get anchored on certain words and metaphors that are based on our peril. Quit being one of them. One of the stories she tells, and I just love this, is Astro Teller, who's at Google X.

So, if you don't know Astro Teller, his job is to do what they call these moonshots. You know, they will give him billions of dollars to try to find the cure for cancer. Billions of dollars to try to, you know, whatever build, build high-speed rail. And he has to get his people to think differently, understanding that they're as a victim to these tropes as any of us are. So he has a thing called the pedestal and the monkey. And he says if your job is to build a monkey on top of who's juggling on top of a pedestal, don't build the pedestal first.

The thing is, we all know how to build pedestals. And if you build the pedestal and then you can't get the monkey to juggle, you have wasted all this time. And he calls it the illusion of progress because you think you're making, look, I got the, the pedestals done. But that was never the problem. You already knew how to do the pedestal. Can you get the monkey to juggle? 'cause If you can't quit. And the exam, the other example, this is a real-world example, and it's going on right now, and it's infuriating, which is there is a high-speed, high-speed rail in California that is set up. It's an idea that was set up to go between San Francisco and LA land they spent a huge amount of money to start building. So they laid track right in the middle where there's flat land.

But there's a problem that everyone just ignored even though it's on the maps, which is there are two mountains that are in the way of San Francisco and LA and Gavin Newsom, handsome Gavin Newsom, good looking fella he just approved more money to lay more track in the flat land. And they have no idea how they're gonna get through these mountains because it, they, they can't necessarily, well, they can't go around them that that's a problem. And blasting through them is a huge problem. So this is the classic thing. They're just doing their pedestal, and they're doing more pedestal. And it's just, it is na it is gonna waste billions and billions and billions of dollars and go nowhere. They need to quit. But it's hard to do. Be, you know, you've heard of like, you know, sunk cost fallacy, you know, when we get into these things, it's like, well, I spent all this time, I spent all this money. Let me just keep going. It's like, no, get out.

Yeah. Call it when you see it. I love this, like the juggling monkey. I'm going to use this at work. For me, it's like really understanding what a client's business problem is. And I think, yes, we see the pedestal because we're really good at building pedestals. And so we really want it to be the pedestal, the monkey. It's so much harder. Yeah. And we oftentimes will set it aside, or we'll wait for it. Like, let's just go straight towards the juggling monkey. Yeah.

Yeah. My co-author Tom Yoan would always say in meetings, what is the problem we're trying to solve? It was always a great reset. Cause we'd be like, okay. We went off on a tangent. Yeah. What is the problem we're trying to solve?

Write it on the board. Yeah. Big. Love that. All right.

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Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Art of Deep Listening

All right. Two more. Five.

Number five. Okay. I've been waiting for this one, and yet you could. We almost did it earlier, but you have trained some of the biggest names in comedy. So I'm curious: Can you train me or lead me in an improv exercise Now? Is there an easy one? Yeah. What people can do at the office? Yep.

Kelly Leonard Second City shares his expertise with Ashley: So we've talked about the importance of listening: 

So this is a thing. Human beings aren't necessarily really good at it. And being good at it is a superpower. Yeah. I think I used the phrase before if I didn't, my friend Nera Il says, which is that if it can't be used for evil, it's not a superpower. So, deep listening is that it is why con men are good at conning people. They are deep listeners but also really healthy, smart, lovely humans are also really deep listeners. So we have an exercise that does a couple of things. It teaches how hard it is to listen, but it also gives us practice and what it means to listen. Okay. So you and I are going to have a conversation. There's really simple, there's one rule, which is the last word that I say or that you say will be the first word that the other person says, okay, so, were gonna do whatever we can do, but you just, you're, so I'm gonna start, and the last word I say is what you need to start you're with and vice versa. And that's what we do. Okay. So one of the things that I do want to talk to you about too is, is the idea of resilience inside improvisation. 'cause I think that's really important,

This podcast has been about important topics. I've loved listening to all the great stories you've brought from TNFA and Steve Corre and all the cool things that happen on stage.

Kelly Leonard Second City advice: 

The stage is interesting. I love performance metaphors. There's a guy named Irvin Goffman who actually second says he started in 1959. He really sort of did his seminal work in 1959. And I think he's a sociologist. And he talks about the fact that human beings have onstage personas, offstage personas, and backstage personas. We are not that doesn't mean that we're schizophrenic. It's that we have many different kinds of sides and selves. And at different times, we're presenting part of this part of that. And too often, we sort of feel like, oh, we just gotta be this one thing. It's like this idea in politics where it's like he changed his mind. You're like, yeah, I would hope you'd change your mind if you got more information that meant, meant that your original opinion was wrong.

I feel wrong all the time, But I think it's important to take the nuances of what makes you feel like you're wrong and turn them into something potentially groundbreaking.

Okay, I'm gonna stop this. 'cause What I loved about this was not hard.

Explore more insights on how to master the “Yes, and” mentality by listening to this podcast with Kelly Leonard Second City

Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Power of Deep Listening

What I loved about this was that you did two. You did two. Then, the two things you have to do, which is you wait and you listen to every single thing I said, 'cause you had to Yeah. To get to that last word. But then you took a beat. You didn't try to like rush it in and be like, octopuses are in the sea, or whatever. You took your moment, and you actually were like, okay, let me take that word and let me find a connection to the thing you're saying. And that might make me pause for a few seconds. And here's the thing. We might think that the pause is gonna make someone else be like, you know, they need that time filled. That's not what's happening. What I'm thinking when you do that is you are taking the time to really be thoughtful in your response.

I appreciate that We could all benefit Yeah. From this sort of slowing down. Yeah. And so that exercise, which is really hard for some people, it is hard for them not to try to form their own response. You know? Cause there's the fear of not looking smart. But it's also hard for them to just slow down, you know? And this does not mean we don't have to speed through everything. And this is increasingly hard in a social media world and in a kind of shortcut world. Mm-hmm. We can communicate via, you know, emoji Mm-hmm. to get across an idea. And really, it's like, I don't, you know, I have yet to read, you know, a great work that was done by emojis.

Yeah. Yeah. We're, we're in the world of like six-second ads and three-second ads. And it's like, okay, how much shorter can we get? Do people do not love ads? Like maybe that's just the thing we need to create content they actually care about.

This is funny, which is funny too. 'cause My 25-year-old son listens primarily to, primarily to long-form podcasts. Mm-hmm.  90-minute podcasts. Yeah. And, and so, so it's like, and, and, and we'll, and they'll go to Marvel movies that are two and a half hours, and it's like, I don't think it's true., I know that there are some studies around shorter attention spans, and I get that. But, you know, a full night at Second City with two accident improv sets is three hours, and we're sold out every night.

I love it. That was really fun. Thanks for doing it. Okay, good. I hope other people do that, too. Alright.

I used to, actually, before when I would do radio interviews, okay. I would always say, please don't tell us to improvise. And, and I, and, and I, and, and we, and we'd say this to other, like, radio stations when Second City people would be, 'cause we definitely didn't think it would translate. And I, I think that was wrong because, like, since Zoom, I've done a number of these things where people are like, let's play a game. And I'm like, oh, okay. Now we have the benefit, I think of having, you know, you and I can sort of see each other, and other people could see us and that sort of thing. But also, I think that was a fear that didn't, it was just more of like, well, what if it doesn't go well? It's like, who cares if it doesn't go well that you can make that the lesson?

There's beauty in that.

Explore more insights on how to master the “Yes, and” mentality by listening to this podcast with Kelly Leonard Second City

Kelly Leonard Second City: Mastering the “Yes, and” Mentality — Keys to Better Networking

Yeah. All right. The last one's four.

Let's do it. All right. So, well, this just, it just ties so nicely into what we just did. One of the things I was just so impressed with in my time with Second City is how you remember everybody's name. We would go down the list, 20 people, and you knew every single person your team did. So, imagine you're at a networking event. You meet 10 people, you remember none of their names. That's usually me. Why do we have such a hard time remembering? And are there any other tips that you can give us to be a better intentional listener?

Kelly Leonard Second City tips to be a better intentional listener: 

All right, so the reason is easy, which is we can only hold so much crap in our brains. I mean, it's just like, you know, and this, this is why I use my wife's brain all the time. Like, there's that, that is, there are if you wanna make fun of me, and there's many things that you can do. I traditionally don't know when Thanksgiving is. And my wife is like, you know, it's on this like very specific Thursday forever for a year. I have other things in my brain. So, I'm terrible with names. I am, and I inherited this from my dad. My dad called everyone man or lady, like in like the sort of hipster fifties way, which, and, and, and he was nice enough that people just like, were like, oh no, it's like a colloquialism for me.

Kelly Leonard Second City continuation tips: 

He really knows my name. And so I think I tend to do that as well. You, you, I, the trick, of course, is you have to gamify it. You, you, you, what you want to do is you meet someone, and you're like, Ashley, you know, who else do I know? Ashley, Nicole, blacks, my friend. Okay. At, you know, and, and you, and you just basically give yourself some practice when, when you meet someone. And if you can also tie it in with like, what are two things I can know about you? One of the things I like to do, well, here's a trick for for if, if you are an introvert and you go into a networking event, I'm sorry. I know it sucks. But here's the thing. That a social scientist and I forget her name, but I had her on the podcast, and she said, oh, make sure you look for odd number groups.

If you go into an even number group, everyone already has a conversational partner. But if you go into an odd number group, you are going to be a conversational partner right away, even if the three people are talking because of that fourth person. And my wife is an introvert, and she had to go to this conference, and she utilized that. She's like, it worked really well. Yeah. I ended up in the right groups. And then, and then you try to sort of like, s and you can't, you're not gonna be able to remember everyone's name. Here's the other thing you do that I've learned that I have to do, which is write stuff down. Like I am, you know, I have so many different kinds of things that I could talk about and things that may be important to me. And just the simple act and, and typing's, okay, but it's not as good. There's science around this. It's not as good as, you know, getting a pen and piece of paper and writing some stuff down. That, 's across the board, actually, for a lot of different things. So one of the, if you find yourself, you're ruminating on something, a bad conversation happens, something at work, whatever, write it out on a piece of paper, then tear it up and throw it away.

Explore more insights on how to master the “Yes, and” mentality by listening to this podcast with Kelly Leonard Second City

Kelly Leonard Second City: Mastering the “Yes, and” Mentality — The Power of Improv in Daily Life

So, my therapist actually told me about this. And this is something that can very much help with things like you need to process something. Your hand just did it. Your brain did it. You sort of put it down there. And guess what? You're throwing it away. You're done. You don't need to look at it again. And that's not a panic. This is not gonna solve real, real-world problems. But I'm not talking about major structural problems. I'm talking are, are the little ways that human beings get in their way every day when they don't need to. Mm-hmm. And I think that's at the root of why improvisation is important for anyone who wants to live a, quite frankly, happier and better life, which is that we don't practice those things.

That will help us navigate all the ambiguity, all the confusion, all the missed connections, and the misunderstandings. And they're inevitable. Those are going to happen. And you can act like they're not going to and not practice, but then it's gonna hit you. And then you're gonna have like it was a bad encounter, and then you're just gonna leave it as a bad encounter. And I think there's just a better way, and I think that way is, is finding ways that you can practice being a better collaborator, a better listener, a very creative partner, a better human. This, at the end of the day, I, I call this stuff human being practice. And if people understand that they, they are not just gonna walk out of an improv class feeling happy 'cause they weren't looking at a phone for three hours, they'll also feel like emboldened to step out in, in, into the world maybe with a bit more courage. And hopefully, there will be some wisdom and kindness. 'cause I think those are the things, those things altogether are the things that we're missing. Right? A lot of people who are exceedingly brave and courageous, we look at, and it's like, oh, but they're not kind. Do you watch Ted Lasso?

Yeah, me too. One of the things I loved about a description one of the writers made about Roy Kent is that he is not nice, but he's kind.

That is true. There is a difference. Yeah. What a great way to end. That was amazing.

Yeah, we did it.

We did it. Congratulations. All 12. This was an art of improv all on its own.

I had to work really hard not to repeat the material.

You did awesome. Was it fun?

Yeah, it was, it was great fun for me. Thank you.

Oh, well, thank you. It was a dream come true for me. So, you know, a lot of our listeners work for brands or agencies. If somebody's really interested in this, what's the best way for them to connect with Second City? And do you have things that you offer agencies and brands to take advantage of?

Oh, absolutely. So, we do tons of brand messaging. We do, on the training side, of course, a lot of what we've talked about. We do those kinds of exercises for teams and different groups. But then also we have some of the funniest people in the world who are very good at short-form content. So whether it's creating internal messaging or external messaging, whether it's working with brands and their audiences to mine for what they care about and understand, one of the things that are so important to understand about a laugh is that that is that's an emotion, and it's a connective emotion. So if you are, you know, trying to get at the essence of what your brand is, and you can understand, oh, everyone laughed at this one thing, and then we can sort of tease out what that one thing is.

That could be a character, an idea, a phrase, or all these different expressions that we use to get at. You know I was talking to Marcus Collins, who's he's at Wyden and Kennedy, and he's also a professor at the University of Michigan. And he was just talking about the simple thing with Coke, Coca-Cola has sold sold forever. The idea is that they're selling happiness. And I'm like, I do not drink soda. I don't keep it in my house, but if I want to, like, if I like giving myself a special treat, I will get a Coke . 'cause I'm under the illusion that it's going to make me happy. And it is sugar water. So I think with, you know, in improv, you know, improv and comedy and all that stuff, all sort of meat at that intersection of, you know, human beings and, and, and how they decide what to do or not to do. You can find all this information on secondcity.com and Second City Works, and you can find me on LinkedIn. I love to sort of interact with the audience.

Awesome. Thank you so much, Kelly.

Thanks, Ashley.