
Workday Playdate · 2026-07-01 · 53 min
Key moments - from our scoring
Substance score
42 / 100
Five dimensions, 20 points each
Anne Libera brings decades of expertise from Second City and Columbia College Chicago to explain why improv is fundamentally a leadership and communication skill, not a path to stand-up comedy. The conversation centers on how improvisation trains people to accept uncertainty, listen deeply, and respond authentically in real-time - core competencies for effective leadership. Libera discusses her work with the University of Chicago's behavioral science program, where improv exercises translate psychological insights into embodied practice. She shares concrete examples: a retired man who learned conversation skills through 'Humor Doesn't Retire,' attorneys and doctors using improv to improve their professional presence, and her new fully-improvised show 'Improv Supernova' at Second City ETC that prioritizes audience connection over joke-telling. The episode also features Erin Diehl's workshop offering (Improve It's 'Thinking Quickly' program) and explains how Viola Spolin's foundational exercises create safe spaces for self-discovery. For leaders and entrepreneurs, the takeaway is that improv provides practicing ground for behavioral change - not intellectual understanding, but embodied skill development through repeated safe practice with others.
Yes. Improv teaches adaptability, listening, and authentic connection skills that transfer directly to leadership. Anne Libera has created improv programs specifically for entrepreneurs in pitching and persuasion, and works with the University of Chicago's behavioral science research to translate psychological insights into improvisation exercises.
Absolutely. Anne Libera herself was not considered funny growing up, and the book 'Funnier' opens with that exact statement. Improv helps people discover their own authentic humor through vulnerability and interaction rather than joke-telling, and teaches communication skills that have nothing to do with being a comedian.
Making things up is a side effect, not the point. Improvisation's actual purpose is to give people practice in behaving differently, connecting with others, and being more open and responsive - skills that develop through repeated exercises with other people.
Building genuine connection and shared journey with the audience creates a unique experience that cannot be replicated, unlike comedy content available everywhere on social media. Having audience members share their real stories first allows performers to weave authentic human details into the show.
Yes, research shows improvisation training strengthens creativity, collaboration, and cognitive flexibility. Anne shares an example of a retired man who took the 'Humor Doesn't Retire' class and, after a year, began joining family conversations rather than isolating - demonstrating that improv teaches embodied behavioral practice.
Our reviewer’s read on each dimension, with quotes from the episode.
There are a handful of genuine insights - the 'thank you because' exercise grounded in Epley's gratitude research, and the recognition+pain+distance comedy framework - but they are surrounded by extensive host monologues, personal anecdotes, affirmations, and fan-girling that dilute the useful content per minute substantially.
we actually designed workshops to use improvisation to teach the insights of behavioral science
what we discovered is that even if only one person is doing it, the other person, uh, finds the conversation to be warmer and more useful
The 'thank you because' reframe of 'yes and' for genuine disagreement is a reasonably fresh and actionable idea, and the three-part comedy theory adds some structure, but the overall improv-equals-leadership thesis is one of the most recycled frameworks in corporate L&D content.
we have people find something that two people find something that they genuinely disagree about...you have to listen for something in what they said that was of value to you...you say thank you because
it is thinking about comedy as a series of practicable choices in the same way that improvisation is
Ann Libera is a genuine practitioner-academic who created the first college comedy-writing major, ran Second City's training center for years, and co-designed research-backed workshops in a formal university partnership - real credentials, though her relevance to B2B operators is indirect rather than firsthand.
I was the head of improv pedagogy for the second science project, which was a partnership between the University of Chicago School for Decision Research and the Second City
I run a college major in comedy writing and performance at Columbia College Chicago
The episode names real researchers (Nick Epley, Xuan Zhao at Stanford), a concrete academic partnership (Second Science Project), and specific alumni, which is above average for this genre, but all outcome claims are vague ('preliminary research,' 'warmer and more useful') and no business metrics are cited.
it comes out of Nick Epley's work on, uh, the Power of Gratitude
Xuan Zhao, who's at Stanford now, did some preliminary research on it. Um, one of the things that we discovered is that even if only one person is doing it, the other person, uh, finds the conversation to be warmer and more useful
The host consistently prioritizes fan appreciation and personal storytelling over substantive follow-up; she never challenges a single claim, frequently interrupts with affirmations, and spends significant airtime on her wedding improv scenes, a missing cat in Charleston, and Josh Johnson stocking shelves at Aldi.
Oh, my God. Chills. Yes.
I had therapy this morning, so I feel like I'm going back. I'm going back in my childhood
Computed from the transcript - who did the talking, and the words that came up most.
In this episode of Workday Playdate, Erin sits down with Anne Libera to explore how improvisation can unlock stronger leadership. From flow states and vulnerability to humor and human behavior, Anne shares why improv is about discovering what's possible. If you've ever wanted to lead with more creativity, communicate with more confidence, or simply become more yourself at work, this episode is for you. Inside This Episode: Discovery Is the Real Superpower: Anne unpacks why the heart of improv - and great leadership - is discovery. Learn how staying curious, present, and open can lead to stronger teams and better decisions. Flow Isn't Just for Artists: Discover what flow feels like for improvisers and leaders alike, and why creating the conditions for flow can boost creativity, innovation, and performance. Improv Is More Than Comedy: Anne busts common myths about improv and explains how these practices help us build new behaviors, embrace vulnerability, and connect more authentically. Try "Thank You Because": Learn one of Anne's favorite improv exercises for strengthening communication, navigating conflict, and creating warmer conversations at work and home.
Transcribed and scored by The B2B Podcast Index.
Speaker A: Have you ever been in a meeting where someone asks a question and suddenly the room goes silent? Everyone looks down at their notes. Someone pretends to adjust their laptop. One brave soul takes a sip of water that lasts about 30 seconds. And then someone finally says the most dangerous words in corporate America. Well, it depends. Today we're talking about how to avoid that moment. How to think faster, listen better, and respond with confidence when the unexpected happens. Because the truth is, leadership is basically improv of and the leaders who understand that have a serious advantage. Hi friends. Welcome back to Workday Play date with Improve It. I'm Erin Diehl. This is the podcast where we explore leadership, communication and culture through play. Because learning does not have to be boring and work definitely does not need to feel like a never ending zoom meeting. This month we are exploring a skill every leader wants. Thinking quickly on your feet. And today's episode is called the Improv Advantage and leadership. Because if there's one place where thinking quickly is required, it's improv. Now, today's guest y', all, first and foremost, my 22 year old self is shaking in her boots like I am sitting here. Interviewing the one, the only Ann Libera. She has dedicated her life to studying comedy, improvisation and how people learn to be funnier and more creative. Now, Ann created the first college program in comedy writing and performance at Columbia College Chicago. She teaches and directs for the Second City in Chicago and around the globe and is the author of Funnier and the Second City Almanac of Improvisation. I said improvisation for a reason now. Which means if anyone understands how improv builds human skills, it's Ann. And before we bring her into the play date, I want to just talk about the real problem most leaders are facing. Before we do that though, I just want to give a quick opportunity here for teams who want to build this exact skill. At Improve It. We are an improv infused talent development company for the new generation of work and we have a workshop specific to this topic. All about thinking quickly. Our thinking quickly on your feet workshop helps teams practice clear communication when the pressure is on. Now this workshop can be delivered in person for groups and of up to 100 people or virtually for groups of up to 50. Through improv based activities and real workplace scenarios, participants practice staying present, organizing their thoughts quickly and delivering their message clearly. Everything centers around one simple formula. Focus plus trust equals your targeted message. Now participants learn to stay present in the moment, communicate clearly and concisely, and deliver the message they actually want. If your team wants to strengthen communication and confidence together you can learn more at, uh, Learn to Improve it dot com. That's Learn to Improve it dot com. Now, back to our play date. So let's talk about this problem. The challenge that most leaders are not struggling with is not intelligence. They are struggling with pressure. When someone asks you a question, unexpectedly, your brain does something fascinating. It switches into performance mode. Instead of listening, you start scripting. Instead of being curious, you start calculating. Instead of responding naturally, you sound impressive or try to sound impressive. And that is the moment when your brain freezes. Improvisers train for the opposite. We train our brains to accept uncertainty, which is basically the entire job description of leadership. So improv, y', all, is truly a, uh, leadership skill. Here's the surprising realization. Improv is not about being funny. It is about being adaptable. Improvisers learn to listen deeply, accept ideas quickly, and build on what is happening in real time. Now, research shows improvisational training strengthens creativity, collaboration, and cognitive flexibility. You're going to hear Ann talk about that here today. In other words, improv helps your brain stay calm when things get unpredictable, which makes improv one of the most powerful leadership development tools out there. And because the best leaders are not the ones with perfect scripts, they are the ones who respond with curiosity and confidence. And that is exactly what Ann Libera teaches. So let's bring Ann today to the play date. Now, as I said, she's an associate professor at Columbia College Chicago, where she created that first program in comedy writing and performance that is the one and only one in the country. She's best known for teaching and directing at the Second City, the legendary Chicago improv theater that launched comedians like Tina Fey, Stephen Colbert, who we'll talk about, Amy Poehler, who we'll talk about, Michael Key, and many others you're also listening to. A graduate of their training program, myself, she also writes books that explore how comedy works and how improvisation shapes creativity and communication through her work and both comedy and education, and helps people understand that improv is not just about being funny. It is about listening deeply, responding in the moment, and building on ideas together. Skills that happen to make incredible leaders. Welcome to the play date and let's play. And first of all, this is literally my improv nerd dream coming true. I'm so excited to chat with you. Welcome to Workday Play Date.
Speaker B: I'm so happy to be here.
Speaker A: Oh, uh, this is like, literally the like 22 year old, um, I'm now in my 40s, but the 22 year old in me is like, what, what this is real life. This is real life. Because you are such a legend in the comedy world, especially in Chicago. My roots are from chicag. So let's just start. I just nerded out on you. Let's set an intention for our time together today. We're talking about thinking quickly on your feet this month on the show. What's an intention that you want to either give receive today? What's a word that comes up for you?
Speaker B: The. This is such an improv word, but it is one of the most important ones to me, which is discover.
Speaker A: Freak. Yeah. Okay, tell me a little bit more. Why. Why that word?
Speaker B: Uh, because it is both. The thing you do when you improvise, when you're improvising in flow, uh, is make discoveries, not go to a predetermined place. Right. But it's also so much of the work of anyone who is leading a group of people, anyone who is, uh, teaching or managing or taking care is that idea of not going in with. I know what is supposed to be, but instead I'm going to discover what is right for now.
Speaker A: Oh, my God, I love it. Right. For now. And you use the word flow, which I love. I love that word so much. Let's just start there. When you talk about discovery and flow flowing as it relates to just improv. Let's start with improv, and then we'll zoom out to. For the. For the. For the leaders on the. On the call. When you talk about flow, what does that feel like in your body? What does that feel like to you?
Speaker B: Well, it is a level of. And this.
Speaker A: This will.
Speaker B: You know, I'm going to go back to, like, really classic Spolin.
Speaker A: Yeah.
Speaker B: Um, where you have a point of concentration, a thing you're doing, so you're not, uh, unmoored. Right. You have this thing you're doing, but because you're doing this thing, you are over and over again making discoveries. And making discoveries not just in your own head, but with other human beings, uh, with the. The ideas that you have, uh, with the world that you're in.
Speaker A: Yeah.
Speaker B: Right. You're seeing things that you don't normally see because you're open to seeing them. You are hearing things in ways normally hear them because you're open to it.
Speaker A: Yes. Oh, my God. And being receptive is so important, too. It's a huge part of it. Okay. We are going to nerd out on some. On some improv, and we're going to bring this around to the. To the leaders on the call, too. But I want to just start with the word improv. When people hear this word, what do you think the biggest misconception is that they have about what it actually is? What do you think people assume?
Speaker B: I think so. Two things. There's the simple thing, which is the idea that when you're improvising, um, you're just making things up.
Speaker A: Yep.
Speaker B: Right. Which you are. I'm not denying that you're making things up, but that. That's the point of it. Because actually the point of it is not the making things up. The making things up is like the sort of side effect.
Speaker A: Yes, yes.
Speaker B: It's maybe the result. But the point of improvisation is to give you an opportunity to learn how to behave differently. Right. Improvisation is practice of people being connection with each other. Improvisation is practice for behaving in new ways. And, you know, originally, Viola Spolin was really interested in performance, being a better actor.
Speaker A: Right, right, right.
Speaker B: Uh, but, but, but what we have discovered at Second City is that it's also a way of generating, uh, new material, of generating comedic material in front of an audience. Yes, but in other worlds, it's a way. And I was talking to you about. I teach a class at Northwestern that is improvisation for entrepreneurs, uh, in pitching and persuasion. It's also a way of generating a different version of yourself. A better, more, uh, open, uh, version of yourself that's not the self you're going to have all the time, but it's a self that you can draw on when you need it.
Speaker A: You just brought up so many feels for me. I had therapy this morning, so I feel like I'm going back. I'm going back in my childhood. Okay. So, uh, let me just say that the moment I walked in the doors at Second City, I'm just gonna say it. I felt like I could take my bra off. I was like, this is where. This is where I belong. These are my people. I understand how. How this all works because it is so freeing. It's, uh. It's allowing you to turn into and. And replace that judgment that you have of yourself. I love that you used it with entrepreneurs. I studied in my early 20s and then came back in my later 20s. And at the time, I was in a recruit, I was in a role at a recruiting firm, which, by the way, never had done recruiting, never had done business development in my life. But everything that I was learning in my classes and doing on the stage was spilling over into my professional life, and it was truly making me a better human. And I just. Exactly what you said. It's the art of being with, of creating with other people. And it's. I hear this a lot, too. People hear the word improv and I think automatically assume you have to be funny. What would you say to that? What would you say to that?
Speaker B: So improvisation isn't jokes. And this goes back to, you know, sort of the path that led to me being a comedy professor, which is my day job.
Speaker A: It's so dope. It's so dope.
Speaker B: I run a college major in comedy writing and performance at Columbia College Chicago. But to understand this is the thing that I got from improvisation is that comedy and humor isn't just jokes. It is recognition of other human beings. It is, ah, connection of the ways in which we are all messed up and in trouble. And one of the things, you know, you talked about your experience, uh, at Second City. You know, I was the head of the artistic director of the training center for many years. And one of the things that really struck me is that I would have students come up to me who are nearing graduation of their program and say, I didn't get into this. To, uh, I got into this thinking I was going to be funny. Right. I got into this thinking that I was going to become a comedian. But you know what? I don't know if I'm going to be a comedian, but what has happened is that my life has changed. I have different relationships than I had before. I am better at my job. I'm getting promoted. And it is all about improvisation being a practice. And yes, uh, because we are human beings and we have pain and we have truth. Ah, we have all these things that are part of comedy. So comedy can come out of improvisation, but it's not a. But the actual work of improvisation is not about the comedy at all. The actual work is about this learning how to behave in new ways that we have never been taught to behave in.
Speaker A: Uh, hey, peeps. I hope you're enjoying the conversation here today. We will be right back after a quick break from our sponsors. Thank you for supporting those who support the show. You are listening to Workday playdate on the Passion Struck Network. Now back to the show. Okay, two rabbit holes I want to go down. Okay, first one. Here we go. First one was when I came to comedy at Second city. This is 2005, 2006. I had been class clown in my high school. Okay? I was trying to be. I had done sketch comedy. I. I've, uh, been a dancer my whole life. So I was very scripted. I was trying to be the funniest person on Stage. And Ann, let me tell you, that don't work. Okay? That does not work. Many, uh, notes later realized that. And then as I learned that, it's really the reactions that people are reacting to your truth in that moment. It became so much more easy and so much more natural. The second piece I want to say about that is just even going through the Second City training programs. There were attorneys, there were doctors. There were all different types of humans coming in to better themselves at their craft using this art form. So what would you say to someone listening? We call our community the Peeps, by the way. What would you say to a peep who is listening, who is thinking, maybe. I mean, I don't live in Chicago, but I know there's a comedy theater down the street. Should I join? I'm a nurse. Should I do that? I'm a leader of a very small team, and I run a small business. Should I do that?
Speaker B: 100%? Because, again, this is about training yourself in. We don't get the opportunity to practice being people.
Speaker A: Yeah, yeah, that's true.
Speaker B: And what improvisation does, really clearly is it gives you exercises that make you better at making connection with other people. It gives you exercises that make you better at, uh, we've actually created as part of. I was, uh, the head of improv pedagogy for the second science project, which was a partnership between the University of Chicago School for, uh, Decision Research and. And the Second City. And we actually designed workshops to use improvisation to teach the insights of behavioral science.
Speaker A: So dope. So dope.
Speaker B: And what this means, though, is. Is that there's not. You can read something. We all have read thousands of business books, thousands of personal development books. And you read and you go, oh, that sounds good.
Speaker A: Right?
Speaker B: That sounds good. I will do that.
Speaker A: Right, Right.
Speaker B: We all have diversity and inclusion workshops. You should behave like this. But we don't get a chance to practice, um, it. We know what it is, we know what it's supposed to be, but we don't get the opportunity to practice this. And what these exercises do. Exercises do what the spolen improv exercises do, what these adapted exercises do is allow you to practice these things as yourself. Yes. Not role playing, not pretending to be somebody else. As you. And then once you've practiced them, you can actually do them in your life.
Speaker A: Oh, my God. It's like, you know, as you mentioned, we are human beings. We're not human doings. We're so. We're so focused in the doing that this really allows us to be in those Moments we drop in. I have to tell you, too. So when I came back to improv in my later 20s, I was getting married. Do you know how much I worked out on the improv stage? Okay. So much.
Speaker B: It was, like, very common.
Speaker A: Yeah. It's. I was like, man, somehow every scene is about wedding planning and getting married. Uh, but truly it was. It was such an. A, uh, form of therapy to allow myself to be myself, but a different version of myself in that time. And even to this day, I don't perform as much as I would like. But when I get to step into those moments of play, it's the best form of therapy. I know. It's the best form of experiential learning that I think exists.
Speaker B: Well, I want to share a story. So I was. I was in a yoga class one day, and a woman was there, found out I worked at Second City. And she said, my father. We had this class called Humor Doesn't Retire. My father. My father takes. Took the Humor Doesn't Retire class because he thinks he's funny. He likes to make jokes about my mom. Ah. And she said, he's been doing it now for a year. And she said, he's not any funnier, by the way. Love it.
Speaker A: I love it.
Speaker B: Um, but she said this year, for the first time, at the holidays, you'd finish Thanksgiving dinner, he would go into his office and shut the door and watch TV instead. This year, for the first time, he came out and joined everybody and sat and talked all night. And she said, I genuinely think that he didn't know how to start doing that. He needed practice.
Speaker A: Yes.
Speaker B: At. At being a human being in conversation.
Speaker A: Yes. Oh, my God. That right there is enough to be like, get up, everyone. Get your loved ones in a class. If people are like, therapy's not for me. Try improv. Truly. Or using it for your tape. Sorry, what were you going to say? And go ahead, go ahead.
Speaker B: Yeah. No, no, because the skill. Because. Because the skills you're going to learn, you're going to get to learn and practice skills that you can use in all sorts of places, not just on the stage.
Speaker A: Yes. Okay. And let me just ask you this too, because you kind of touched on it with this story. When people say, I'm not funny, what is your response to them? Because, for example, you know, my dad's not funny. What would you, uh. If somebody thinking. Who is listening today is thinking to themselves, well, I'm not funny, what is your response to that? To that limiting belief?
Speaker B: So, first of all, that is the first line of the intro of my book. My book is called Funnier.
Speaker A: Yes.
Speaker B: Uh, uh, and, uh, the very first line is, I am not funny. If you ask anyone I grew up with, if you ask people that I went to school with, they would be like, she's working in comedy.
Speaker A: Stop, stop, stop.
Speaker B: Absolutely.
Speaker A: Okay. Keep going, though. I'm here for it. Cause I find you funny. I find you very, like.
Speaker B: Thank you.
Speaker A: In the moment. Funny. You're just.
Speaker B: Well, I've been doing this for a really long time.
Speaker A: Yes.
Speaker B: Uh, uh, but this is. To me, this is not the point. The point is because when I started the degree in comedy, uh, the feedback I got was, well, aren't people just fun or they're not. And I think people believe that about all of these sort of communication skills. You either have them or you don't. You're either funny or you're not. Um, and the thing is, is that I found the ways in which. Through improvisation, I found the ways in which I am funny. Uh, and the ways in which I am funny is seeing something that is different. The ways in which I am funny is in interaction. The ways in which I am not a funny joke teller, although I'm actually good at fixing jokes. This is my. This is my Second City superpower, is that I'm really good at, like, going, okay, if you move that word from here to here.
Speaker A: Yep.
Speaker B: It's gonna be funnier.
Speaker A: Yep. Yep.
Speaker B: Um, but what I learned what was funny about me, and I learned that I could be funny in all sorts of ways. And this is one of the. One of the things I think that is brilliant about improvisation is it forces you to use yourself. M. It forces you to use the things that are maybe a little bit vulnerable about you. Um, and it forces you then to do, you know, what behavioral scientists call self disclosure? And there's a real genuine power in a little bit of self disclosure. It's very funny. We love it when we love to find out things about other people, and we love really little weird things about other people that we would never think would be a joke. Right. Um. Uh, but it also, when you do that and people laugh at it, it makes them see you as having a mind.
Speaker A: Ah, ah, ah. Interesting.
Speaker B: Okay. So it's a way of making connection. And that's what we left. You know, when we're in an audience at a Second City show, we are watching people's minds working.
Speaker A: Totally. Totally.
Speaker B: And, uh, one of the other things I'm doing right now, because I have nine jobs.
Speaker A: You do. You really do but they're all awesome.
Speaker B: I do. They're amazing jobs. Uh, I am currently directing the Second City ETC show, which is one of the Second City's two resident stages. And we are doing a full. For the first time in Second City's history, we are doing a fully improvised two act show.
Speaker A: Really?
Speaker B: At the ETC Stage. Yes.
Speaker A: That is crazy and amazing. I'm so curious, like, why the shift? We need to talk about this. This is me nerding out, like, why the shift?
Speaker B: Some of it was just saying, what is something that so many people. We are so comedied out in our world.
Speaker A: Yeah.
Speaker B: So many people have comedy on their Instagram reels and their TikToks and, you know, um, that is all sort of joke based. And we're saying, what is the reason to be in a room with other people. Right. In a comedy club? Uh, and not to do the standup thing of crowd work where they talk to the audience and then they make fun of them. Uh, but instead to be in an audience with people in community.
Speaker A: Love it. Love that.
Speaker B: So the show is actually called Improv Supernova. And we spend the first, roughly 10 minutes of the show, rather than going to the audience and saying, can we have a suggestion of a blah, blah, blah, Instead we spend probably the first 20 minutes of the show talking to them.
Speaker A: Yes.
Speaker B: Having them tell us stories about what they care about. First of all, everyone is fascinated by everybody else's stories. We could literally spend the entire show just having people talk about their lives.
Speaker A: Right.
Speaker B: Um, uh, but it creates this incredible connection and people share all sorts of details about their lives, all sorts of things about what they care about, all sorts of odd stories. And then we take that and we use all of that fabula, all that storytelling, and put it into a show that is discovery for that audience. And I can't tell you the feeling. And you certainly know from. From a classic improv show perspective, but this sort of build where we've all been on a journey together, that is the only time this audience is going to be in that journey at the same time.
Speaker A: Okay. Oh, yes. Keep going. Keep going, Ann. Keep going. I'm just, like, jazzed. I'm jazzed because I saw something very similar to this recently and I was like, it just brought so much joy to my heart. It was here in Charleston. And so do you know M edie Patterson? Righteous gemstones. Um. Oh, yeah, yeah, she lives here. They film that show here. So I'm. I'm not in Chicago as much as I would like to be anymore, but this is my little improv fix here in Charleston. Bluebird Improv came and they did a very similar type show. Oh, my God. But it was like they. They talked to the audience. We had, um, we. People in the audience were talking about this cat that was missing in Charleston that had been on all of the. What are. The neighborhood. You know, the neighborhood website. Everybody posts things, um, next door. Next door, yes. Everybody had been talking about this cat. And then there was an Uber Eats driver that stole somebody's food or something. It was like this whole situation. But everyone was so invested in these two really dumb stories that were so dumb in theory and that, of course, they were news. They were front page news here in Charleston right now.
Speaker B: Sure.
Speaker A: And we were, like, enamored with what they did on stage. It. I left that show and being like, this was the best use of two hours of my life. Like I was. Because it's community.
Speaker B: Yes, exactly. And I. And all those guys, those are all former. The Bluebird improv guys are all former Second City guys. I, uh, directed, uh, several of them when they were here at Second City.
Speaker A: Tim, Matt.
Speaker B: Yeah. Joe. Uh, and, um, Brad.
Speaker A: And you're. You are legit a badass. You were legit a badass. You really are. Like, this is truly talking to you is. Is fulfilling every improv dream I've ever had in my life, because I'm just blaming these people that were headlining a massive theater here. And you are the teacher of those people. And Stephen Colbert is, like, your bestie. I do know that.
Speaker B: Yes. I got him. I got him his job at Second City working in the box office. He was my roommate in college.
Speaker A: I'm totally digressing. We're going all over the place. This show is not linear. Um, and I'm sorry, peeps, this one's. This one's for me. Okay.
Speaker B: Neither is improv. Improv is not linear. Improv is about making discoveries and then finding what the core of the thing is.
Speaker A: And that was our intention. So we are still discovering together. And I love this. Okay, so I have so many questions for you when you hear about your standout students just crushing it in life. First question. Did you know that they would always rise because they were talented to. How does it make you feel? How. How do you feel when you witness greatness that you were a part of?
Speaker B: Well, so here's. Here's an interesting thing. There are some people who were in my class, and they were just amazing. They were amazing. Then I have a vivid memory of, uh, having Amy Poehler in my in my class, and. And really just going, oh, you're really good.
Speaker A: Yeah. Okay. Okay. You did know that that is a thing?
Speaker B: Uh, you know, I don't. I didn't teach her anything. She taught me by being my student. So there. There are. But this is an interesting thing. So there are people who are always brilliant, and then there are people who are fine. And then over the course of time, begin to make discoveries about themselves and find the thing that does work for them and find their thing. And that's, for me, the sort of as a teacher, as a director, that's the stuff that, uh, you know, just makes my heart swell to see what happens as someone really discovers their voice. Someone has that moment, uh, either in an improvisation or on stage, and you can see the beginnings of, oh, this is my thing. Yeah, this is what I do, or this is how I do it. And I think again, to talk about the brilliance of improvisation as a teaching and training tool is that it allows the person to discover it for themselves. Right? Instead of me telling you, this is who you are, which is, you know, by the way, this is classic theater, uh, training. This is who you are. This is what you should do. Now, as an improv teacher, I'm going to set up a space and an exercise in which you discover how you do the thing that you do.
Speaker A: Oh, my God. Chills. Yes.
Speaker B: Right?
Speaker A: M. Right.
Speaker B: And that is so powerful, dude.
Speaker A: That's it. That's like, the whole point how you discover the thing that you do. And then they feel it. And when you feel it, you know how to respond. Again, when it happens, when you. When your body has a physical reaction, you will remember.
Speaker B: Yes. And you can repeat it then. Yes, you can repeat it in different circumstances because it belongs to you. It doesn't belong to somebody else who is dumping the knowledge on you.
Speaker A: I just. I really wanna. Just take a moment. I could go down like the comedy rabbit hole forever. But our peeps want these tangible takeaways, and I want to give it to them because you are the master. So if someone listening right now is a leader of a team and they're wondering, how do I create this space to give my team the opportunity to be who they are and do what they do, do you have any. Any advice you would give them? Maybe it's an activity. Maybe it's just a simple one or two questions.
Speaker B: All right, so I'm gonna give you two things, okay? Number one is really thinking about how are you creating space for people to do the thing that you want them to do? Rather than telling them what to do.
Speaker A: Yes, right.
Speaker B: Lots and lots and lots of times. And I say this as a second city director, my job, particularly when I'm directing improv, because I can't tell them what to do.
Speaker A: Sure, sure.
Speaker B: Right. So how am I creating a space in which they have the ability to do the things that I want them to do? And lots and lots and lots of leaders do the opposite.
Speaker A: Totally.
Speaker B: Right. Lots and lots of leaders create spaces in which that actually it's hard to do. Hard for people to do because they're so afraid of negative consequences that they don't create space for positive consequences.
Speaker A: That's it.
Speaker B: Right.
Speaker A: Mhm.
Speaker B: So that's number one. Number two, and this is a, uh, brilliant thing that I use all the time. Uh, and it was part of, it was an exercise that we created as part of the second science project. Um, and we were talking about yes. And we were talking about how. Yes. And is brilliant. But it's, uh, uh, it feels dangerous. You know, when you teach, uh, corporate groups about it, they're like, but I can't.
Speaker A: Yes.
Speaker B: And all the time.
Speaker A: Right.
Speaker B: And they're right, right, right, right. Uh, uh, you can't always, always use yes and. But, uh, we wanted to create a place where people could use something like yes. And in a situation in which they were in genuine disagreement with somebody. So you're actually not going to say yes.
Speaker A: Right, right, right.
Speaker B: How do you, how do you still keep the element of yes and in that. And we created an exercise. The name of the exercise is thank you because love. And it comes out of Nick Epley's work on, uh, the Power of Gratitude. We tend not to think, we tend not to anticipate that people will, uh, be happy that we said thank you.
Speaker A: Yep. Yeah.
Speaker B: When actually we do.
Speaker A: They really do. And it's free. It's a free thing.
Speaker B: Oh yeah. Weird thank you notes. People love thank you notes.
Speaker A: Handwritten note is hard to come by in 2026.
Speaker B: Yes. Um, but, but so what we do with this exercise is we have people and uh, we have people do, uh, this exercise really, as themselves. We have them find something that two people find something that they genuinely disagree about. Right. So they're not pretending to disagree about it. They genuinely disagree about it. But like low stakes, like crunchy, uh, versus smooth peanut butter.
Speaker A: Oh, that's a hot topic.
Speaker B: Yes. Or the way that the toilet paper goes under over the roll. M. People feel very strongly about that, by the way.
Speaker A: I have some opinions about both. Okay, keep going. Okay.
Speaker B: Anyway, um, uh, Coke versus Pepsi. But so they're genuinely in disagreement about something and we have them talk. And the whole, the first level is to just try to convince your partner.
Speaker A: Right?
Speaker B: Just try to convince your partner. And then we say, okay, you're going to continue to try to convince your partner. But before you convince your partner, you have to listen for something in what they said that was of value to you. You um, don't have to agree with them.
Speaker A: Mhm.
Speaker B: You don't have to agree with them. You just have to listen for something that is of value to you. And before you argue your point, you say thank you because. And you talk about the thing that was of value to you that they said. And then you can say whatever you want to say.
Speaker A: Yep.
Speaker B: I love is magic. We actually, uh, Xuan Zhao, who's at Stanford now, did some preliminary research on it. Um, one of the things that we discovered is that even if only one person is doing it, the other person, uh, finds the conversation to be warmer and more useful.
Speaker A: Interesting. Okay.
Speaker B: And I use this all the time in my life.
Speaker A: I'm sure. I was just gonna say, I'm just. I was literally thinking of all the ways, like a, A, uh, one on one where somebody is giving. Like if you are, you have a direct report and you happen to have something that your direct report says that you don't agree with. I'm speaking for a friend here. And you could say, you could say thank you because. And then it's almost. It's. So what I'm hearing, if I'm thinking about putting this into context, is it's almost like yes and, but yes and feels more like you are agreeing. Even though we know it doesn't mean you agree. It's an acknowledgement that they spoke and that they gave ideas. And then you can add your thought. Right. Even though it sort of breaks the ice of I don't agree with you. But thank you and thank you so much. And here's this. Is that right?
Speaker B: Yes. And there it is.
Speaker A: Ah.
Speaker B: See what I did there? Uh, it forces you to listen not for the things. So it gives you a point of concentration, to use Spallan's term. You're listening not for the things that you disagree with. You're listening for the things that you do agree with.
Speaker A: Oh my God. See, they're right there.
Speaker B: Right? So, so.
Speaker A: Oh, oh, girl. And hold hands. This is this. Hold on. Yes. Because I'm, I'm a, I'm a woo woo gal. Okay. And I'm, I'm a big like Louise. Hey, Wayne Dyer, very, you know, loving this. And I'm currently reading a book by Louise Hay and I. I truly believe our thoughts and our words affect how we appear to the whole, to. To the whole, to the collective. Right. This right here is putting not only our thoughts into motion, but our words into motion. So we are automatically changing how we're. How we're consuming information in our brain. I love this concept so much. Uh, we're hitting the frontal lobe, the prefrontal cortex, all of those things scientifically. And then the conversation feels warmer and more compelling, which leads to a greater outcome.
Speaker B: Yes. So again, you may not come to agreement, but you are going to find the areas of agreement and you're going to leave that conversation in a very different place with the other person.
Speaker A: Ann.
Speaker B: Right.
Speaker A: Dude. This woman. Woman. Not dude, but woman. This is just, uh, helpful for everyday life. Okay. Not just with teams. You can use this. Your personal, professional. All of it. All of it. Um, and it makes so much sense on, ah, on a, like, on a communicative level. And then from a scientific, psychological level, it makes complete sense. I'm so. I love that you're doing this research. I love that you are putting. And you're a professor. So, like, this. We. We need this. We need more of this. Because it. Honestly, as a. As an improv nerd myself, it helps a lot of the people who learn with their head and also believe with their head, not their heart. I can feel. I know how improv makes me feel. But a lot of people need the research to back that up. And so, just so grateful you exist and you're doing this work because it's bringing so much to the forefront for so many humans. I truly believe we all need an improv class in our life. This world would be different. We said that before we hit record. I want to just pivot real quick because you have a lot of exciting things. You have a new book. I want to talk about the book. I want to talk about. Why did you write this book Funnier. And why did you write it now? What caused. Because this is your second book. Third book. Second book.
Speaker B: Second book. Second book. Second book. First book was the Second City Almanac M of improvisation, which I love. Yeah. Um, so I created this college, uh, program in comedy writing and performance. And it really came out of the fact we have something called the comedy studies semester, uh, that we've been doing at Second City, and it's like a semester abroad in the study of comedy. And what became clear m pretty quickly was that this was a College major, that there were students for whom this is what they wanted to do. Uh, that these skills and this work was gonna be of use to them. And we have lots and lots of students who are working. I've got two different, uh, graduates of the program who are now, uh, writing for Saturday Night Live. Uh, Adie Bryant, who did the program.
Speaker A: Uh, that's a small name out there, Aidy Bryant.
Speaker B: I'm just gonna draw some people. Um, uh, but it became clear that the way of teaching comedy and the way that I think about it, and it is improvisation based, it is practical, it is thinking, uh, about comedy in a new way, which is that, uh, you're. Maybe one of the important things is that it's not thinking of comedy as jokes or as something that special people can do. It is thinking about comedy as a series of practicable choices in the same way that improvisation is. Right. And so my theory of comedy that I sort of put together, and it's based on years and years of theory and research. Humor, uh, theory from the past. But, um, is that when we create comedy, we're using three things. We're using recognition.
Speaker A: Truth.
Speaker B: Um, you can get a laugh just from saying something that is true about you. Right? Um, that is the discovery part of improvisation. That's exactly what we're talking about in terms of the storytelling. Right. And then again, by the way, you can get a laugh just from using recognition, which I think is, on its own, a discovery for a lot of people. They think, oh, I have to tell a joke. No, you can just share something that's true about you and people will laugh 1,000%. So recognition. Second thing is that comedy is also pain. We're sharing something that is uncomfortable, even surprise, is a kind of pain. Incongruity, uh, is a kind of pain. Right. But if it's just truth and pain, that's, uh, not comedy. Yep, tragedy.
Speaker A: That's tragedy.
Speaker B: So what the best comedians do is they frame it, right? Uh, and they frame it. The term I use is distance. And so that could be temporal distance. Right? Tragedy plus time equals comedy. That could be physical distance. Mel Brooks used to say, uh, uh, comedy is when I cut my finger. Uh, sorry, Tragedy is when I cut my finger. Comedy's when you fall in an open sewer and die. Right?
Speaker A: Oh, see, I'm even laughing at that concept.
Speaker B: No, it's funny. No, Mel Brooks. It's funny. He's funny. Uh, uh, it can be psychological distance.
Speaker A: Yep.
Speaker B: And so these are all the sort of tools of comedy. And I needed to sort of put it in a place where I could give these clear, concrete tools to a large number of people who are interested in how to create comedy, but also how to use comedy. I think we all know that humor is a superpower, but there's so much lore around. Either you're funny or you're not. Right. And when I. And the title of the book comes from the fact that when I started the major, somebody at the higher ups of the college I was at said, well, is comedy something you can teach? I mean, aren't people funny or they're not? And I'm like, that's not the point.
Speaker A: Right.
Speaker B: Yes. There are people who are not funny.
Speaker A: Right, Right.
Speaker B: There, uh, are people who are very funny, naturally talented at it. But the thing is, I'm not looking to do that. What I'm looking to do is help people who are interested in comedy be funnier.
Speaker A: M. Right.
Speaker B: And that there are ways, there are tools and techniques and ways of thinking about the world. And there are different kinds of comedy than just jokes. Comedy, uh, can be physical comedy. Comedy can be storytelling.
Speaker A: Yes.
Speaker B: Comedy. You know, our favorite comedians, you know, Colbert is maybe a really perfect example of this. Right. When you listen to Stephen, he doesn't tell a lot of jokes. What you are interested in, what you find funny is his perspective and point of view. The world that he paints. Right.
Speaker A: He paints so many worlds. And I was listening to your episode with John Miles, Passion Struck Network, and I loved that you said, uh, you met Stephen in a class at Northwestern, and then it was like on the walk home that you realized that he was so funny because he painted this world for you with his own views.
Speaker B: Yes. Who completely. This incredibly long story about Mr. Blinky. Those traffic, uh, uh, cones that they set up to set aside construction. And he created this entire story that pulled together, uh, uh, the concept of PI. PI and, uh, uh, Asian mandalas and circles. I mean, it's. And you can listen to it, and it is both lovely, but there's also this sort of take on it.
Speaker A: Yeah, yeah.
Speaker B: Right. That is like no one else's take. And our favorite comedians, the ones that we love the most. Right. The ones that we're like, oh, this is for me, are the ones who do that. Right.
Speaker A: Who.
Speaker B: We don't just love their jokes. We are with them because we feel like they are speaking brain to brain with us.
Speaker A: Yes.
Speaker B: And we laugh because we recognize it on a deep level, even though we would never have said it in exactly that way.
Speaker A: Oh, God. Do you know, um, Josh Johnson? He's a. He's a comic. He's not an improviser. He. So this is one of my stories of my own improv. Just Journey. He, um. Him and I were in class together at Annoyance, and he was working at Aldi, just like, uh, um, doing the gross, you know, with stock and shelves. And then he would go to these standup classes every single night. After. After we would do, like a class or performance, he would. He would just go do open mics. He worked. He works with Trevor Noah. Was on tour with Trevor Noah. He's a writer for Trevor Noah. He has his own tour. And his comedy is exactly what you're saying. He takes you. He's. He's also very, very, very, um, highbrow. He never. He never swears. He never, uh, gives anything. That's a dark look. He actually. It's almost like a TED Talk mixed with comedy in an uplifting way.
Speaker B: Sure. You feel like you're learning something like John Oliver does, too, right?
Speaker A: Yes. It's brilliant. And it's like you're sitting there and all you want to do, you're lingering onto every single word, and that's what you're teaching. And funnier is you're teaching how to do that, and you're giving us tangible tips and tricks and tools, and you're allowing human beings who might not have the opportunity to study at a theater or might not live in a city where theater is accessible the opportunity to do that. So, Ann, where in the world can everyone get your book? Tell them. Okay.
Speaker B: It's called A Practical Theory of Comedy. It is available. It's, uh, Northwestern University Press, is the publisher, but is available, uh, on Amazon. Or you can tell your favorite, uh, local independent bookseller. Yes, to order it, please. Uh, because we support, uh, independent bookstores, um, but it is widely available. And, uh, I, uh, I encourage people to get it, but I also encourage people to use it.
Speaker A: Yes. You want it to be dog eared. These are one of the books we're gonna highlight. Dog Ear. Come back to use, uh, the bits
Speaker B: that work for you and actually practice.
Speaker A: Yes.
Speaker B: Being a comedian.
Speaker A: Okay.
Speaker B: Practice comedy.
Speaker A: And if people want to find you. How did they do that?
Speaker B: Uh, so I am, uh, a libra@secondcity.com.
Speaker A: love it. Okay, we got your event. We got it there. We got your.
Speaker B: Um, but I also. I'm also at Columbia College Chicago, uh, where I am, uh, an associate professor of comedy writing and performance. So either of those places is the best place to find me. I am on LinkedIn. Uh, so you can find me on LinkedIn. I have to up my social media game.
Speaker A: Don't, don't, don't, don't. Just don't, you know, So I actually, I love social media. I should say that. But I think exactly what you're doing is working. You are. You are such a light in this world. And this is my last question, and then I'm gonna. I want to just give you your flowers one more time. But we always ask this. You know, we made a lot of discoveries today. We had a lot of fun discovering things with you. And this is called workday Play date for a reason. So how are you going to make your workday at. You're at Second City right now. You're at work. How are you going to make it more playful? What are you going to do?
Speaker B: Well, see, I. I have this. I have rehearsal today.
Speaker A: Yeah. And that's play, quite literally. Yes.
Speaker B: I get. I get to go. I get to get into a theater with six of the genuinely greatest improvisers on the planet. Yes. Uh, and we're gonna, uh. Uh, we want to figure out a way to do a. Uh. We have. We have a terrific musical director. His name is John Love. Uh, and our goal for today is to figure out a way to do a new kind of musical improv with John.
Speaker A: So fun. So. And that is. That is like, I literally.
Speaker B: We're just gonna play music. Yes. Screw around.
Speaker A: Um, this is the best answer I've ever had on this show. Sorry, everyone else. The best answer. Okay. And I just. I just want to tell you this one more time. You are a light for so many of us in this world of comedy. And I have taken it and. And just using it, used it as a therapy tool myself, as a. As a learning tool. It changed my life. The work that you do, the work that you are helping others do, you've changed so many lives. So I hope. Here are your flowers. I want you to receive them, and I want you to own that, because what you do, you just being you, has changed hundreds of thousands of lives. So take that. I'm so honored you came on the show. Thank you so much. Thank you. And I have discovered. I discovered more than I even could have imagined in this. And I could talk to you for hours. But thank you.
Speaker B: Thank you. It's been a pleasure.
Speaker A: Oh. Um. All right, Ann, we'll have you back sometime. Third book. You're coming back for the third. Okay. Hello, my peeps. It is time for your playdate practice. I could talk to Ann all day long, but I want you to try to put her exercise. Thank you because into practice. So in your next meeting, conversation, or brainstorming session, I want you to listen carefully to someone's idea and let's say it's an idea that you don't necessarily agree with. Okay? These things happen every single day. Instead of responding and getting defensive, try your very first two words to be thank you because and say why you're giving them thanks and then add your opinion. Try this the next time you feel a conversation kind of getting to that icky point where you know you're disagreeing but you want to remain calm and you also don't want to remain steady in your relationship. Thank you because. And we've heard the research that is backed behind this. And in theory, it is a practice that I promise you will change the way you show up not only for yourself, but for your team. So my peeps, that is your playdate practice. This show was an epic show, one that I will remember forever. I hope it touched you. Until next time, I want you to keep playing, keep learning, and keep bringing the improv advantage into your leadership. I'll see you soon.
Speaker B: Um,
Speaker A: Sam? Mhm?