A conversation with Kelly Leonard. Executive Director, Learning and Applied Improvisation at Second City Works.

So we know that, that’s how we create our shows at Second City. We have a 12 week process, we develop in front of the audience, and we know the first four weeks there’s going to be a lot of seemingly garbage, but we allow that seemingly garbage to surface because there might be a gem actually inside there, especially when sort of looked at a different way.” – Kelly Leonard

In this episode of Control the Room, I had the pleasure of speaking with Kelly Leonard about his three-plus decades managing the legendary sketch comedy group The Second City.  He begins with reflections on the shared origins of team improvisation and social work.  Later, Kelly explores self-verification theory and how it can lead to stronger relationships faster.   We also discuss group brainstorming and breaking down silos.  Listen in for a plan to save the world by improving listening skills.

Show Highlights

[1:50] How Kelly Got His Start.

[18:21] Your Team Is Only As Strong As Its Ability To Compensate For Its Weekend Members

[23:02] A Case For Brainstorming 

[32:35] Learning To Be Unafraid

[41:25] Fight Like You’re Right Listen Like You’re Wrong

Kelly on LinkedIn

Second City on Twitter

Second City on Instagram

About the Guest

Kelly Leonard has worked with some of the most legendary folks in comedy at The Second City. Now he works at the intersection of improvisation and behavioral science: helping people learn to wisely improvise through life.

About Voltage Control

Voltage Control is a change agency that helps enterprises sustain innovation and teams work better together with custom-designed meetings and workshops, both in-person and virtual. Our master facilitators offer trusted guidance and custom coaching to companies who want to transform ineffective meetings, reignite stalled projects, and cut through assumptions. Based in Austin, Voltage Control designs and leads public and private workshops that range from small meetings to large conference-style gatherings.

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Full Transcript

Douglas: Welcome to the Control the Room podcast. A series devoted to the exploration of meeting culture and uncovering cures to the common meeting. Some meetings have tight control and others are loose. To control the room means achieving outcomes while striking a balance between imposing and removing structure, asserting and distributing power, leaning in and leaning out, all in the service of having a truly magical meeting.

Thanks for listening. If you’d like to join us live for a session sometime, you can join our weekly Control the Room Facilitation Lab. It’s a free event to meet fellow facilitators and explore new techniques so you can apply the things you learn in the podcast in real time with other facilitators. Sign up today at voltage control.com/facilitation-lab. If you’d like to learn more about my book Magical Meetings, you can download the Magical Meetings Quick Start Guide, a free PDF reference with some of the most important pieces of advice from the book. Download a copy today at magicalmeetings.com.

Today I’m with Kelly Leonard at The Second City where he is the Executive Director of Learning and Applied Improvisation. He’s also the author of Yes And: Lessons from The Second City. For over two decades, Kelly was producer of The Second City, hiring and developing original reviews with such folks as Stephen Colbert, Tina Faye, Steve Carroll, Keegan-Michael Key, Seth Myers and Amy Poehler. Welcome to the show, Kelly.

Kelly: Hi, thanks. Thanks. I’m happy to be here.

Douglas: Yeah, great to have you, been looking forward to this. Well, as usual, let’s get started with a little bit about how you got your start.

Kelly: Okay, so I graduated college in 1988 and I wanted to be a playwright. That was sort of my passion. I’m the youngest of six boys. My dad was a TV and film guy who reviewed theater in Chicago. So he knew a bunch of people. And he got me a bunch of informational interviews, which was great. Bernie Sahlins, who was the founder of Second City, he had sold Second City about four years earlier, was starting a new theater and he hired me. He said like, “Yeah, you can be a production assistant, but I’m not starting for six months. Let me call over to Second City and we’ll get you a job there.” I don’t know what I was expecting, but I wasn’t expecting to be taken to the back bar and have my first gig in theater be a dishwasher because he was not pleasant.

The other guy who got hired that week also to wash dishes was John Favreau, the film director. And we both had mullets and my wife has photographic evidence of this that she uses to shame me. So I washed dishes for a while and then I hosted in the room and I went to go work for Bernie in that theater, which was called the Willow Street Carnival, we later referred to it as Second City with hats. It didn’t do well, it folded. So I went back and my friend Ann hired me in the box office and I sort of kept getting promoted and I was writing plays during my off hours and submitting them and having some success. But in 1992 I got offered the job to be the associate producer of The Second City, which is the guy who hires all the talent and oversees all the productions.

It was sort of a thing I couldn’t turn down, so I took it. And if one thinks back to what was happening in Chicago in 1992, my first cast included Steve Carell, Stephen Colbert and Amy Sedaris. I hired Tina Faye, Amy Poehler, Rachel Dratch, Jason Sudeikis, Cecily Strong. Tons of great people. And it really was a dream job. I did that until 2015 when I co-wrote the book Yes, And: which is about how Second City takes its improv practices and pedagogy into businesses and into caregiving spaces. And really my first part of my career was improv on stage. And then my second chapter, which I’m in now is improv offstage, improv everywhere else.

Douglas: I love this idea of improv everywhere and big fan of the book. I wanted to come back to The Second City and hats, and it reminded me of a few things that come up. It was a consistent thread through the book of trying things, experimenting, learning, and just kind of dusting yourself off when it wasn’t quite right and figuring it out. I remember there was quite a few stories like that.

Kelly: Yeah, I mean look, we live in a culture unfortunately that acts as if failure is something that shouldn’t happen, when in fact we learn when we get it wrong, we don’t learn when we get it right. Carol Dweck, she writes about growth mindset, talks about when a student gets something wrong, you shouldn’t say, “You got it wrong,” you should say, “Not yet,” because we all get things wrong.

So improv, and I don’t know if you know where all this stuff came from, I certainly talk about in the book, but many of the exercises and games that we still teach at Second City were developed by a social worker by the name of [inaudible 00:05:08]. And she was working at Jane Addams Hull House in the 1920s and 1930s and her job was to better assimilate immigrant children who were coming into her care.

So she created all these exercises and games that allowed people to communicate with empathy and collaborate. Her son, Paul Sills, was studying at the University of Chicago. He taught these games to his friends. People like Mike Nichols and Elaine May. They formed the first improvisational theater in the country called The Compass Players. That’s in 1957. That morphs into The Second City by 1959.

So social work is where this stuff came from. So it’s really about how we can practice our human being skills, our human skills, because we’re not good listeners. We’re afraid of failure. We have a lot of judgment of others and judgment of self. And you cannot be creative if you are self judging or you’re judging others. You simply can’t. And creativity does not happen alone. It’s with other people, it’s with audiences, all those things. So many of the improv practices that we teach for people to become really good comedians, improvisers, actors, comedians, are equally as effective for the kind of skills that we use in our life, because we are born without scripts and we are improvising every day. All of us are.

Douglas: Yeah, I’m a big fan of y’all. In fact, I’m also a big nerd about facilitation and improv cards and games and there’s an amazing card deck, a box set of her work that’s just like, it’s so massive. I mean, it’s like 110 games or something. It’s crazy. I love your point about not yet, and it reminds me of like 409 and WD-40 and all these classic stories of no one got it right on the first try.

Kelly: That’s right. I mean, post-it notes. Listerine, I just found this out from a guest on my podcast that Listerine was originally used to treat gonorrhea. Very different use right now. So yeah, if we can get in that space where we’re practiced in recognizing we’re going to fail, that’s okay, go back at it. We’re really then operating in the scientific method, which is experimentation over and over and over again. This is how anything new comes to life, is that someone has to try it and it’s likely not going to succeed on the first, second or third try.

So we know that, that’s how we create our shows at Second City. We have a 12 week process, we develop in front of the audience, and we know the first four weeks there’s going to be a lot of seemingly garbage, but we allow that seemingly garbage to surface because there might be a gem actually inside there, especially when sort of looked at a different way.

So this sort of embedded innovation practice that exists at Second City is borne of teaching individuals better skills for things like listening, paying attention. And then our work with the behavioral science community has just deepened that. So as we’ve sort of worked with the various academics that we work with, they’ll give us insights that we didn’t know. I mean, we teach at Second City to be others focused, and I think we all kind of know what that means, paying attention to other people. But when we learn about things, there’s William Swan who’s a professor down in Texas, came up with a thing called self verification theory. And this was fascinating to me.

The idea is I think most of us think we want to be seen as our best selves, our smartest selves, but Swan says that’s not true. We want to be seen as we see ourselves. So if I see myself as clumsy, it’s important that you see me as clumsy so you won’t throw me a ball. But human beings are tricky and I’m not going to tell you that. I might not even be working with that at the top of my mind. I think self verification theory also maybe explains why people date assholes. If you have low self-esteem and you have someone treat you, you have no esteem, you’re scratching an itch.

Douglas: That’s pretty deep. I think that could actually really help people that are in all sorts of collaborative moments better understand the full person that’s shown up in the room. Right? Because I think a lot of times when people are collaborating, they look at their coworkers very two dimensionally.

Kelly: For sure. And Nick Epley, who’s one of the scientists we work with, has all this research that we really don’t get it right in these rooms most of the time with other people. He marks it at around 20 to 30% that we’re perceiving correctly. And we’ve created exercises around this too, because the other thing that he notes in his work is that individuals tend not to share specifics about themselves because they think other people don’t care. When in fact, even seemingly banal specifics could lead to faster, better relationships. So when we saw this literature and he was going to be teaching in an executive education program, my wife Ann actually developed an exercise to go along with it called Universal Unique. So we pair up two people, person A, person B, and we pick up an old topic like grocery shopping and we say, “Person A, in a minute, explain how human beings grocery shop.” “You get in a car, you go to the store, whatever.”

They do that [inaudible 00:10:23]. And then she goes back and says, “Okay, think for a moment about how you personally grocery shop. Now take a minute and do that.” Inevitably there’s laughter in the room and people are saying, “Oh, I learned so much about you just from hearing that.” And we’re talking about grocery shopping, we’re not talking about deep stuff, but when we draw from the specifics of our lives, I mean this is why Seinfeld was funny. It’s all these seemingly, again, banal specifics, but they end up being true. And when we can see someone as true, multidimensional, as you said, that changes the game. That is where you go from okay teams to brilliant, high performing teams.

Douglas: I love that point you made about better, faster relationships, because I think that’s a key piece that so many people miss is the importance of relationships. It’s not just about the operational pieces that we have to do or the logistics. If we’re going to work together, really there needs to be a relational foundation there.

Kelly: Relationships are everything. The longest study that I know that’s ever been done is called the Grant Study in Harvard. And it’s looked at a group of men who are now in their eighties, so this is an 80 year old study, and they’re trying to define happiness, what causes happiness. And there’s one result across all domains with all these men and it’s their relationships.

And it doesn’t mean that it’s a couple who never bickers. They could bicker all the time, but they’re together and they’re okay and they get over their bickering. But having rich relationships with a lot of people is a definition of happiness. It also leads to better health outcomes, to wealth, all those things. So I got this without putting words to it when I started working at Second City, in part because we build these ensembles, these highly functioning ensembles and you could sort of see it, but then being introduced to the sort of academic underpinnings, it’s like, oh, this is life changing stuff.

If we can know this and then if we can practice this, that’s the key, because we don’t practice being human really. We might have a mindfulness practice, we might work out, we might play a team sport or whatever. And honestly the person who’s going to figure out how to make improv yoga will be a billionaire. And I wish it were me, I don’t think it’s going to be. But we really need, and we do these workshops all the time with people, we need to practice this stuff. Because it’s not like you go to the gym once and you’re good. Listening takes work. And especially listening to your spouse. Because I’ve been married for a couple decades and I still have to work at put my phone down, listen to everything she’s saying, put my attention on her, because it’s just easier to do the other thing.

Douglas: Yeah, it comes back to a really solid point that you have in the book of just listening to understand.

Kelly: Yeah. And again that takes work because people don’t share all of it, and they might not even know all of it. I mean, I’ve certainly been in therapy long enough to realize that. That human beings are storytelling machines and we really like easy patterns, so when we lock onto something that seems true, we anchor on it and we’re like, oh that’s it. And then like anything, whenever you interrogate something, and we know this from looking at our past, when you interrogate something you’re like, oh, I didn’t know this was going on and that was going on. I didn’t know they had this belief that was different from my belief. I just assumed it was all working. And sometimes it does, despite all that, which is amazing. But the reality in terms of really successful outcomes, if it’s in your job, it’s in your relationships, any of that stuff is when you truly see the other person and they see that you see them and vice versa.

Douglas: I think that point about them noticing that they’ve been seeing is so key. It reminds me of a study that Slack did. They have this futures forum where they’re investigating work and the future of work and one of the statistics was that 73% of leaders think they’re being transparent while less than half of the employees think the leaders are transparent. Their perception of these things matter less than how they’re perceived on the other end.

Kelly: That’s totally right. So I think it’s important, this is especially true for leaders as you’re saying, which is you can’t make a ton of assumptions and you’ve got to work even harder to get people to tell you the truth. So when I’m working in a leadership position at Second City and there’s someone relatively new, I make sure that I move from behind my desk, I sit next to them. Sometimes I lower my status if I can. And here’s a big thing, I ask them questions and I ask them for advice. That changes the relationship in really positive ways, especially if there’s a power dynamic there. So you have to be aware of what is the dynamic and what’s the space we’re sitting in, because that says something too, it’s different in a conference room than it is in office than it is in front of other people.

My friend Kim Scott who wrote the book Radical Candor, one of the reasons I love her work so much is that it really speaks to the idea that you… Let’s say you have to do a performance review. Do not criticize someone in public, praise them in public, do that. That’s a good thing. But if you have a critique, you take that away, just the two of you, and recognize that you can’t be operating in radical candor unless the person knows that you care for them personally. Otherwise it’s obnoxious aggression. And to get to radical candor takes everything we’re talking about. It takes a really intentional building of a mutually appreciated relationship. The dynamic as we were sort of talking about, it’s not just you. It’s not even necessarily just the other person. There are lots of different dynamics that are taking place here. So be aware as you can of all the factors that might go into how this person thinks about working with you.

Douglas: I want to come back to the point I made earlier about you using these opportunities for learning, not only in your product but also in your culture. I know that in the book you spoke about kind of intentionally looking at diversity of the ensembles and how you support just cultural changes. I think that’s a higher level of being than even just using the techniques to make the product better.

Kelly: And I don’t want to pretend that we nailed it because we haven’t. During the sort of social justice uprising, a lot of crap was unearthed that folks didn’t know or perceive or understand. And I remember Jon Carr, who used to be our executive producer, we had heard complaints about artwork on the walls. And neither John or I really understood what that was. He’s an African American male, I’m a white male. And so I said, “Well let’s go down and look.” And these drawings that were done by an illustrator who worked at Playboy over the years, Bill [inaudible 00:17:20], he did drawings of every cast. And as we started looking at some of these drawings we’re like, oh no, there’s a Caucasian person with a sombrero. Oh no, there’s someone wearing a hijab, a white person wearing it.

And then Dan Castellaneta who’s Homer Simpson did this very funny Hitler bit that was satiric, but if you just see a picture of a guy dressed as Hitler with no context, and I understand it’s a comedy theater, but I imagine many people looked at that picture and were uncomfortable. And actually when you go to a place for, I worked at Second City 34 years, so you stop seeing things, and this was an eye opener. So I know for myself, I’ve had to re-dig into interrogating my own behavior and my own thinking as well as double down on the improv stuff. Because the improv stuff is great for this. It is all about inclusion and it’s about maintaining equity.

In an ensemble, there’s a phrase that we’ve all heard, your team is only as good as its weakest member. And we say it differently, we say your team is only as good as its ability to compensate for its weakest member. Because one of us is going to be the weakest member at some time and that’s going to shift off. So if you’re really operating as an ensemble, everyone’s got your back, everyone’s got your back and you have everyone’s back. That is not a way that I find most businesses, they’re not teaching that, that’s not in the employee handbook and it should be.

Douglas: Well especially if there’s any kind of stack ranking going on, it’s the exact opposite, right? It’s like we’re putting a spotlight on who’s the weakest versus how we could support each other. And I think it’s a real reductive way of looking at things, because in a complex world, if we stack each other around all these different situations and scenarios and skills, someone’s going to be at the bottom at some point when you look at it from a different angle. And so having this perspective of supporting each other makes us more resilient to whatever’s thrown at us.

Kelly: Yeah, and if someone’s sitting in last, there might be reasons, if you haven’t asked. There could be other stuff going on. They might not know what to do. Maybe you didn’t train them well enough, whatever. I mean, I’ve worked with so many people over the years and I can count on one hand the number of people I’m like, yeah, I would just not work with this person. Almost everyone that I’ve worked with has value to bring to the table. It was often a matter of whether our system was set up for them to benefit or not. So we’re trying to get better. I think we’re very good at the behaviors at Second City, the individual and group behaviors, that is our strong suit. And we have systems like the process for creating our show that are amazing. We need to now, and we got bought by a new owner and we have a new CEO and we’re very clearly talking about this. How do we make the business operate as powerfully, as equitably as the art does? And if we can do that, we got it. I’m encouraged by where we’re going with this.

Douglas: That’s amazing. I love that. And I really want to come back to this idea of it’s easy to stop seeing things. It reminds me of when you’re driving on the road to and from work or whatever and you’ve driven that stretch of highway many, many times. You get to a point where there’s some days where you’re like, whoa, I don’t even remember the last two minutes of that drive because it’s ingrained in my memory and my brain shut off. And that happens at work and in all sorts of ways. I think that point you made about just not seeing stuff, and it’s a real testament to you and the team that when it surfaced you’re willing to embrace it because it can be scary for that to happen. I think a lot of people shut those kinds of things down because they don’t want to embrace that.

Kelly: Oh sure. No, no, no. Because there’s shame. I mean, if someone’s calling you out on a thing you said, I don’t care if it’s 25, 26, 27 years ago, they were hurt by the thing I said and I had to own that. And I also wasn’t about and shouldn’t be centering myself inside that story. So that does take work. But this is all related to the way we think. Danny Kahneman, who wrote Thinking, Fast and Slow talks about system one, system two brain. So our system one brain is the shortcut and we need two. There’s so many bits of information coming in for us to process, we have to eliminate. We have to just, oh, that’s a man. And it might not be later and that might be funny, but system two is where we can deliberate and go more slowly.

The cool thing about when you’re improvising is you’re doing both. You’re going back and forth, system one, system two, system one, system two. Which is why Second City trained folk are such incredible divergent thinkers. So I’ve interviewed a bunch of people who deal in navigating ambiguity and paradox and they’re all like, “Man, I’d love to study your six main stage cast members going through this process.” Actually we have an academic coming in next month to look at the show, look at the process, and seeing if they can do that. Because we tape the shows every night and the improv sets were in process.

I don’t know if you’ve seen this, there’s been so many articles about the fact that brainstorming doesn’t work. And they’re like, “Oh, there’s all this research, brainstorming doesn’t work.” And I’m like, that’s pretty ridiculous because what you’ve never done is study a small team. Because to have the research be valid, you need to look at 3000, 4,000, 10,000 people. But the reality is most of us don’t work like that. We don’t work just in duos or trios or whatever it is. We probably have a team of 10 to 12 or whatever, six in the case of a Second City cast.

I will guarantee you, I mean you can call it brainstorming, you can call it something else, that you’re not getting to great ideas by everyone working in a silo. It is ridiculous. It is when someone else can add to your idea. In our work we say, when you’re doing this work, you need to bring a brick, not a cathedral. If you just bring your cathedral, it’s not going to get added to. And I have my brick, you have your brick and we’re going to build this thing together. Again, how it works in the world. This is another bad thing our culture does, which is this myth of the sole creative. Like Steve Jobs didn’t invent the iPhone, that got brought to him. Now, was he a genius in terms of design and marketing? Sure. But in no world did he operate alone. I mean, Edison was like this too. Edison had literally a factory of people inventing the things that he put his name on. But somehow the American myth needs it to be one white guy.

Douglas: That’s definitely a thing that has been perpetuated. And coming back to the brainstorming piece, I think the reason that folks love to crucify that, if you will, is because so many people get it wrong from a perspective of structure and rules. To your point, if people are doing it and everyone’s bringing cathedrals, it’s not going to work. Or if people are in a place where they can’t sit in that exploratory space and they have to inject the constraints too early, and there’s lots of reasons why I think it doesn’t work and it’s a lot more inflammatory to say brainstorming doesn’t work than it is to be like, “Well, if you look at the details, this is why it’s not working.”

Kelly: Yeah. I’ve seen the research and I believe it that the person who talks the most tends to get their way. Honestly that’s why I’ve been successful in my career. I’m not afraid to talk the most. Here’s a great example of this. My wife and I have traveled a lot and we traveled a lot to Europe with Second City casts. And inevitably everyone will follow me. I am terrible at directions, but I will just move to the top of the line and start walking somewhere until Anne has to remind me that I’m terrible at directions and I’m going the wrong way and I should be following her. And I’m like, this is such a great reminder because I just sort of assume that I’m in charge and I’m a tall white guy. So it’s really important, again, especially for those of us who are in these leadership positions, to take a look at ourselves and make room for all the voices. Because introverts offer a world to us because they’re more deliberative. And again, when you shut up and just look around, you see more. So I want input from that person.

Douglas: The other thing I’ve seen to be effective there is some of these folks that are quiet or sometimes extroverts but they’re the type of people that like to process things a little more.

Kelly: Yeah, yeah.

Douglas: And so giving them a little bit of a heads up before we go into the thing around what are we diving into so they can get some ideas rolling before. So I see a lot of times people brainstorm like, okay, let’s brainstorm. Some heads up will help a lot of people.

Kelly: Yeah. I mean set the table. This is also a thing that… And we’ve been talking about this a lot at Second City, we got to get better at setting the table. What’s the expectation from this project or the show? What looks like success to you? Here’s what success looks like to me. So that then we can do check-ins to make sure we’re on the right path. And then afterwards, whether a thing works or not, we can maybe understand why. And if it didn’t work, we’ll have data and info for it to work better next time. All of that stuff is hugely important.

But the speed, there’s just not enough people and the days go by and it’s hard and everyone’s busy. And so there’s all these really, really good reasons to not do it right. But any success that I’ve seen in my decades at Second City came from us slowing down, trusting the process, trusting each other, and that’s when we make beautiful things.

Douglas: That’s incredible. I love it. You made a comment about laughter a little bit ago, and I think you were talking about the fast thinking and this is a man and later that might not be the case. I recently read an article about laughter and how laughter shows up in nature. There are other animals who laugh. And apparently it’s an evolutional thing where we laugh to let everyone know that things are okay. So it’s a release of tension, it’s a release of fear. And so you kind of describe that, right? Because when the joke gets set up and the information is incongruent and then we get the release, then it creates the laughter. And I thought that, wow, how cool is that? It’s an evolutionary mechanism that’s helped us survive.

Kelly: Yeah. So I’m married to a tenured comedy professor who’s just about to hand in her second book and it’s all theory, comedy theory. And so she goes into this exact space of, we used it as a way in very early days to, as you say, signal to everyone that like, oh, this thing I thought was a threat or whatever isn’t. And so that’s that release. The other recent research that I’ve seen is that the same part of the brain that processes an insight is the part of the brain that processes a joke. Again being like the aha ha ha. So when you understand that, you can apply that really powerfully in a variety of contexts. Advertising. So what we know is we want someone to have an emotional reaction to our brand. Effective use of comedy. What’s the thing they’re going to laugh about when it comes to your brand? If you can bottle that, that’s amazing.

I mean, it always makes me laugh that probably billions of dollars are spent on advertising and a lot of comedic based advertising and how many comedy professionals are in the advertising world. I’ve met a lot of people in advertising and they’re not very funny. And also that’s another myth of the sole creative, that it’s like, “Oh, just this guy, he’s our main guy. Stick him in a room and he’ll be able to do this for all your different brands.” That’s not how it works. That’s not how it works. So part of my wife’s theory around comedy is that if you look at it like a mixing board, you’re mixing truth, pain and distance. And truth can be just recognition, and then pain is some level of pain that’s appropriate to the situation. So right after 9/11, you can’t make jokes about it, especially in New York. A year after 9/11, you probably still can’t in New York, but you could in Chicago. And that’s a matter of distance and pain mixing together.

I write about that in the book, where we did a scene, satirical scene a year after Columbine. And this freshman at Northwestern who was at Columbine just ran screaming from the room and had a really heart to heart conversation of we wouldn’t do this if we were in Columbine because you still don’t have that distance, but the rest of us are here and it’s a historical fact that we’re kind of playing with to make a satiric point. And we weren’t making fun of it, but it was too close for her. And I get it.

Douglas: Yeah. And that shows up in the workplace too. If we’re not relating, we’re not understanding where people are, it’s hard to be cognizant of those things and take them into account.

Kelly: Yeah, I’ve interviewed a bunch of people around the idea of suffering at work, and I think this is now very top of mind for many HR departments because all of a sudden after the pandemic everyone realizes that, oh, mental health is a thing. And it’s not something that is rare. People have mental health issues, a ton of people do. They just didn’t talk about it. And when you don’t talk about it, that is a bad thing. You are pushing a bad thing down that is going to come out in some really, really negative way at some point either to yourself, your spouse, your kids, your friends, who knows.

So when we can acknowledge people’s pain, and my friend Heidi Brooks at Yale does a thing where every time she’s teaching a new cohort, first day of class, she goes, “Okay, before we start anything, I’m going to hand out a blank piece of paper and a pen to everyone. Don’t put your name on this piece of paper, but write down some pain you’re experiencing right now.” And she’ll get anything from a sprained ankle to a recent divorce to a death of a loved one. And she just reads those out and it’s like empathy steroids for that class.

Douglas: That’s amazing. I love it. I want to bring up something that I’d written down that I wanted to maybe hit on, and that was this idea of learning to be unafraid. And it’s so provocative, and it kind of ties a little bit back to what we were talking about with the laughter piece, because getting to the laugh, we might have to create a sense of uncertainty or a sense of fear. And so when you’re engaging in these improv type activities, you’re having to move through that liminal space that may feel a bit frightening. So learning to be unafraid and kind of embracing the fear, I don’t know, I’d love to hear some further thoughts on that.

Kelly: Yeah. So Del Close, the famous improv guru, talks about following the fear. Rick Thomas, another really bright improv teacher, director, actor, he has the phrase, “You need to fall into the crack in the game,” which I love. And that requires you to visit some stuff that might be a little troubling for you or others. At worst when we create a Second City show, it’s going to be funny, but what we’re shooting for is funny and art. We want to say something about the human condition. And there is no joy without suffering, and that is just true. And we do try to hide I think a lot from the suffering. But if we can explore it and then come out the other end with some really great comedy, that’s my favorite stuff that I see in any art form, but especially in really smart comedy, is that it’s provocative and it’s human and it doesn’t always need to be political.

A piece that I do not find political at all is about Trump. It’s John Mulaney’s horse in the hospital bit that Trump is like a horse in the hospital. What’s happening with the horse in the hospital, what floor? When I see the horse in the hospital, what’s going to happen? It’s just very, very funny because I think it’s getting at something that I don’t care if you’re on the right or left, you get what that’s about. You get the idea of the kind of mayhem that this particular figure presents. And you may be for that, for whatever your reasons are, you may be highly against that like I am for other kinds of reasons. But it’s true. So I think that no one got into improv comedy because they’re fully self-actualized. We’re not the place where the peaceful mind comes to rest.

No, you’re coming here because something happened or you’re restless and you need to work it out with your friends, which is what happens. So I love all the talent that comes through Second City. I remember we’ve been hired to create a series of PSAs about mental health using comedy. And so I sent out an email to, we have this massive email list, it’s all the talent, to basically say, “Hey, anyone have experience with mental illness in this regard? We got this PSA.” The amount of emails I got back was like 90% of the talent. I mean it really was. Oh, all right. And I don’t know why, that should be obvious to me, but it wasn’t and it really sort of came home. I know this having gone through a personal tragedy myself, is that if you take the time to ask someone or you share your grief journey or something with someone else, they’re going to share something that they haven’t told you. They may be telling it to a therapist or someone else hopefully. But a lot of people out there are in pain.

Douglas: Here at Voltage Control we’re big fans of Ted Lasso because it’s such a great and very popular display of just great coaching and great facilitation. I mean, just some of the jokes and had some real depth to what it means to take care of humans. And they covered some mental health stuff I think pretty gracefully, and also with a real reality. I think there’s a lot of people that are in that space of being fearful of getting help. Anyway, it was really, really quite good.

Kelly: Well the connect point there for me, and I’ll share, So there’s a number of writers on staff who are close friends of ours, obviously Jason is a Second City alum. Four years ago, our daughter, Nora, when she was 16, got diagnosed with cancer and she died a year later. So it’s been three years. And we got a call, it was Nora’s birthday, I think it was the first or second anniversary, from [inaudible 00:37:01] Ashley Nicole Black who writes on the series, and she was working on season two as a writer and she said, “Hey, we decided to name a character and base a character after Nora,” and that’s her goddaughter, and she’s wearing the green head scarf, which is what Nora used to always wear because Ashley and our friend Chelsea had babysat her and they were both working on the show.

So that ethic doesn’t just happen on the show. It was this beautiful tribute that they gave to us that will exist forever because these humans are sort of, again, drenched in this improv mindset of care. And we actually had created an improvisation for caregivers program previous to all of this. So we’d already sauntered down that alley. And so we used it in our own experience when Nora was in the hospital. It’s harder in terms of the sort of grief and trauma part of it. I was less prepared for that. But then again, I got gifted a book by Bessel van der Kolk, and I’m forgetting the name of it, but it’s about how trauma lives in the body. And towards the end of the book, there’s a whole section on improv. And his son had gotten into improv and realized that this is something that, because it’s embodied, an embodied practice, could be helpful for people who are undergoing trauma.

That’s another world I live in. We also in improv say you got to play the scene and not the scene you want to be in. So I don’t want to be in this scene. Who would, that’s madness, but I’m in it. And so being in it means the best way I can take care of myself and others is by focusing on the other person, by making them look good, by truly listening, by being open and curious. We have this idea that you need to replace blame with curiosity. If you can remain curious, especially in the face of complex situations, your success rate is going to be higher than others.

Douglas: Wow. What an amazing story. Thank you for sharing that. And we certainly have had our share of grief here at Voltage Control, and we lost a team member almost a year ago now and have spent a bunch of work trying to memorialize her in a number of ways. And I’m glad that they did that on the show. I had no idea. So now that’s another thing that I can carry with me as a special little memory of that show.

Kelly: Yeah, yeah, no, it was lovely. And her school built a park and named it after her at Chicago Waldorf School. You lose someone, which is terrible and awful, but what I found is trying to keep her, she’s with me, and these other sort of reminders are there as well, which are lovely. But yeah, it’s a journey.

Douglas: Amazing. Well I’m glad that people are recognizing her. I think that’s so important to hear the stories and to remember and such a great way to heal. And gosh, I wanted to always appreciate ending with a little bit of dialogue around what can be possible if we continue to do this kind of work. And we were sort of hinting at that in that last bit there around if more people are showing up in these ways and helping each other heal, I think it creates more harmony, greater ability to cope and be human.

Kelly: We had a four year program at the University of Chicago Booth School of Business called the Second Science Project that looked at behavioral science through the lens of improvisation and vice versa. When Heather Caruso, who I co-led that program with, she’s a social scientist, I offered this proposition to her. I said, “If only we did this, if only we improved everyone’s listening by 2%. Do you think that would change the world?” And we both said yes, I have no doubt. More things need to be done than just that, but if you start with that sort of basic premise or you believe something like that. And I think that could apply to a number of different areas that we’re talking about.

Carl  is a retired academic and he has a great phrase that I often end my keynotes with, which is, “You need to fight like you’re right and listen like you’re wrong.” I think that that embodies everything. Be passionate and throw out your ideas and care about them and fight for them. And then if you are able to listen like you’re wrong, you’re going to have the humility that can create other kinds of opportunity, because none of us know it all and all of us need each other.

Especially the world we live in right now where it feels like 50% of the country is fighting with the other 50%, or cult 48 or whatever it is, I get it, but it’s not doing us good, it’s doing no one good. And we use terms like canceling and blocking and muting and I’m just like, oh my God, if we know, science tells us, the thing that gets us through is relationships, why are we all fighting? And again, you need to fight for some stuff, and representation and equity and all that, fight like mad for that. But if we can also extend grace, if we can give someone our gratitude, if we can really listen to them, I think you’re going to find that most of us have more in common than the opposite.

Douglas: I agree. And what an amazing thing to use as fuel for our commitment or our practices, we just got to increase it 2%.

Kelly: That’s it. Yeah. You’re not going to change people, people don’t change like that. But to get to a better outcome, just simply to get to a better outcome, put all your focus on the person across from you and try to do that as much as you can.

Douglas: So I want to give you an opportunity to leave our listeners with a final thought.

Kelly: Yeah. Okay. So I host a podcast called ‘Getting to Yes, And’ for Second City and WGN Radio. And I get to interview lots of cool people with their books. And there’s a concept that was introduced to me by Annie Duke. So Annie was an academic who is coming up on her PhD years ago and she got sick and she had stop and she needed money, she did not come from money. And she was trying to figure out what she could do. And her brother, who was a professional poker player said, “Why don’t you do what I do?” And so she did, and for the next 18 years she paid professional poker and made millions and millions and millions of dollars. She is now back at Wharton to get her PhD, and she’s written a couple successful books, but her new one is called Quit.

And here’s the concept, it blew me away and I’m finding useful when I’m navigating complexity. So she talks to Astro Teller at Google’s X. So he leads a division of the company that is looking for these loon shots. They’ve 10 years to cure cancer or 10 years to build whatever, and they have to quit a lot of these projects because they’ve got to see progress. So he has a concept that he teaches all his people at Google X, and it’s called the monkey and the pedestal. And the idea here is, if your job is to teach a monkey to recite Shakespeare on a pedestal, don’t build the pedestal first, because it’ll give you the illusion of progress. Because if you can’t get the monkey to recite Shakespeare, you’re done, you’re quitting, and you go to the next thing.

The amount of pedestal building I have done in my career is massive. So really when I’m thinking about a new project or a new show or a new program or whatever, this is the thing I’m going to apply first, which is, all right, what’s the hardest part of this thing? Let’s make sure we can do that, because we all know how to build pedestals, I can do that in my sleep.

Douglas: Amazing. Thank you for reminding me of this because it’s actually something that’s going to become invaluable for me right now. And I hadn’t thought about it in a while, so thanks for the reminder. Of course I highly encourage people to check out the book. It’s fantastic. And of course Second City, if you’re in Chicago, I mean, gosh, what a fun excursion. And thanks so much for being here today. I feel like we could talk for at least a couple more hours, but every good thing has to come to an end. So I really appreciate you taking the time, Kelly.

Kelly: Thanks Douglas, I appreciate it.

Douglas: Thanks for joining me for another episode of Control the Room. Don’t forget to subscribe to receive updates when new episodes are released. If you want to know more, head over to our blog where I post weekly articles and resources about radical inclusion, team health and working better. voltagecontrol.com.