Improv means business

Commical - Season 3 episode 4 with Kelly Leonard

Published 9 September 2026 on the Chasing Albert website, Apple podcasts, Spotify, Amazon Music and Youtube.

[00:00:00] Marie: Hi, everybody, and welcome back to Commical. I have an, a very exciting interview for you guys, but mostly for me 'cause I'm a massive fan of both Kelly Leonard and of Second City. Welcome, Kelly.

[00:00:17] Kelly Leonard: Hi, thanks for having me

[00:00:19] Marie: My pleasure. Kelly is the vice president of creative strategy, innovation, and business development at Second City, the iconic improv theater and improv school, and also corporate training company.

[00:00:34] Kelly Leonard: Yep

[00:00:34] Marie: tell us a bit about Second City.

[00:00:36] Kelly Leonard: So Second City is probably best known for all the famous American and Canadian comedians who've, who've come out of our theater. So we opened our doors in 1959, but the story kinda starts in the '20s and '30s on the South Side of Chicago. There was a social worker by the name of Viola Spolin, and her job was to better integrate immigrant children and neighborhood children into her [00:01:00]care.

[00:01:00] Kelly Leonard: So she invented all these improv games and wrote the bible of improv, uh, called Improvisation for the Theater. Um, her son, Paul Sills, was studying at the University of Chicago, loved these games, taught them to his friends, people like Mike Nichols, Elaine May, Alan Arkin, and they formed the first improvisational theater in the world, uh, called The Compass Theater.

[00:01:21] Kelly Leonard: That's in 1955, and that morphs into the Second City when we opened in 1959. Now, we didn't just do improv. We used, and still do, use improvisation to create sketch comedy shows. Uh, you might be familiar with Saturday Night Live. That entire format was taken from Second City, and of course, most of that first cast came from Second City.

[00:01:42] Kelly Leonard: So we've got the theaters in Chicago and Toronto. We have training centers in those locations. As you m- mentioned, we do, uh, a lot of corporate work. Uh, the, the world has figured out that employees need to learn how to work without a script,

[00:01:58] Marie: Угу

[00:01:58] Kelly Leonard: we've been doing that for decades. [00:02:00] Um, we also have television and film projects and, and other stuff we do, but it's, it's, it's been, you know, about 67 years, and we're still here.

[00:02:09] Kelly Leonard: And you've been there quite a while. You've gone-

[00:02:13] Marie: side of the business, is that right?

[00:02:15] Kelly Leonard: I started out as a dishwasher, so I started out at, as a staff member with the horrible job of cleaning beer glasses. Uh, 'cause there was no... When I say dishwasher, I was literally doing the... We didn't have an electronic dishwasher. Kelly Leonard was the dishwasher.

[00:02:30] Kelly Leonard: The other guy who got hired as a dishwasher that week with me was the film director, Jon Favreau, uh, who was not a film director there, he was a dishwasher.

[00:02:39] Marie: Sasha got it.

[00:02:40] Kelly Leonard: and we both had mullets. Uh, so I, I started washing dishes, and then I hosted the room, and then I worked in the box office. And all this time, the reason I took these menial jobs at Second City, and this is in the '80s, uh, was I wanted to be a playwright.

[00:02:56] Kelly Leonard: And the advice I'd b- was given was, "Work in a theater. Just, [00:03:00]like, start there." And, and it was good, good advice. But then in 1992, there was a bunch of changes, and they asked me if I wanted to become the producer of Second City. Uh, I would become the third producer in the history of the Second City, and certainly the youngest at 26.

[00:03:14] Kelly Leonard: And so I ran Second City ostensibly from, um, 1992 to around 2015. Um, and then I wrote my book, Yes, And?, which was about how we take our improv pedagogy in, into the workplaces. Um, so yeah, I, I've done a lot in my 38 years here.

[00:03:33] Marie: So someone must have looked at one of your beer glasses and said, "Look how clean this glass is. You know what? This guy would be amazing as a producer."

[00:03:41] Kelly Leonard: I can guarantee you at Second City in 1988, no one was, like, complimenting us on our cleanliness. Uh, I think what... I, I mean, it is very much right place, right time, and a lot of luck. Um, and, and unbeknownst to even myself at the time, I had an entrepreneurial streak. So, [00:04:00] you know, Second City was so popular, and yet we really hadn't, like, done any sort of, uh...

[00:04:08] Kelly Leonard: There was no, there was at that point no budgets. Uh, there was, there was no one, like, looking at

[00:04:12] Marie: a

[00:04:13] Kelly Leonard: performance or- Yeah, you had to do that ... Yeah, yeah. And, and so, and, and, like, we were dropping calls left and right. So, like, when I came in, like, in the box office, I was like, "Maybe we'll get a phone sequencing machine, and we can process these calls and figure out when busy times are and staff up."

[00:04:26] Kelly Leonard: So a lot of stuff I was able to do just 'cause no one had, had even thought about doing it because, you know, the, the, the enemy of innovation can often be success. And so I think we're very lucky that I get bored easily. Um, and so I was able, even though we were successful, to, like, put in systems and start to, you know, uh, make changes that then real- really helped the theater.

[00:04:48] Kelly Leonard: When we were ready to grow and do different things, we were able to do that.

[00:04:53] Marie: at what point did you guys figure out, and I mean, I'll go into this deeper later, but I, it, I can't help but think right now, at [00:05:00] what point did Second City go, "Hang on a second, is, a skill is vital in organizations that can really help build trust and collaboration"? When did that penny drop?

[00:05:17] Kelly Leonard: Uh, that penny dropped when we realized that in our classes, and this is in the '80s, at Second City, uh, people who had no interest in getting onto Saturday Night Live were taking the classes. And when we found out why they were taking the classes, they were business people who thought maybe it would help them be more creative in their jobs, be more innovative, be a better teammate.

[00:05:40] Kelly Leonard: So it was really the students were sort of sh- showing us that, that this stuff had value. And right around that time, John Cleese had made a name for himself with a company called Video Arts, uh, which if you remember Fawlty Towers, uh, he, he did a very clever thing where he basically used that concept to show [00:06:00]people how not to run a business.

[00:06:02] Kelly Leonard: So do not be like Basil Fawlty. And, and that became a very successful business. So really before we were doing the improv, uh, training, we were doing Second City comedy shorts, uh, for companies, uh, to help them, you know, sometimes for internal training, someti-times for external messaging. I would say when we started, it was 80% that, 80% content, 20%, um, teaching, and that is flipped today.

[00:06:33] Kelly Leonard: It is 80% training and 20% content. We still, we still do the content, just not as much

[00:06:40] Marie: That's insane

[00:06:41] Kelly Leonard: Угу That's what the value, I- And now Yeah, it, it's, it evolved over time, right? Uh,

[00:06:51] Marie: Yeah

[00:06:52] Kelly Leonard: there were ... Certainly we were a live entertainment company. The, the internet didn't exist, right, at this point, at le- at least as far as, you know, [00:07:00]people knew about DARPA, but not, not as we do it.

[00:07:02] Kelly Leonard: So we were doing live stuff, and then video, and, and, and that made sense, and then a little bit of the training, and then I think it was really, uh, bef- the, the reason we got the contract for the book, for the Yes And book, was that the world had woken up, and this is in the, you know, uh, 20- I think we started writing it in 2013, 2014.

[00:07:23] Kelly Leonard: The, the world had woken up to this improv thing, in particular Silicon Valley. So Z- Zappos had, uh, a, a Yes And lending library. Um, when we wrote the book, like I got booked at Microsoft, at Twitter, at the Code Conference. I mean, it was just like that, the, the idea that, you know, improv would make sense to people who experience startup culture, um, it, you know, it's an, it's an easy, it's, it's an easy jump.

[00:07:53] Kelly Leonard: Um, and, and then, then that got other stuff rolling, right? So people started seeing cutting edge Silicon Valley, [00:08:00] um, are, are interested, so, you know, then Nike comes calling or, you know, whoever. We've worked with every probably Fortune 500 company at a certain, at a certain point. Um, but yeah, it, it's, uh ... And, and actually the content, mostly what we do is we started about a decade ago, uh, a thing called Real Biz Shorts, which, uh- Yeah

[00:08:19] Kelly Leonard: is short form, uh, little fun- funny shorts that go along with ethics and compliance training. So basically the boring ethics and compliance training that we all have to take at some point, uh, sometimes we'll have Second City sketches pop up to illustrate a, a j- a very important point they just wanna make sure you get, so we're gonna make you laugh.

[00:08:39] Kelly Leonard: So that kind of, that kind of relevance through comedy I think is an interesting thing, which it wouldn't s- Yeah. And it wouldn't surprise me if that doesn't become more of a thing y- yeah, as we move forward, 'cause we're all trying to grab people's attention in the world we live in right now is very difficult.

[00:08:57] Marie: Right? And I feel like with the rise of social [00:09:00] media, uh, people, companies have been forced to accept that short, funny content is what people want. They've been forced to accept that. When I think about, uh, the Australian market, um, I've worked in PR and marketing for a very, very, very long time, that includes internal comms, right?

[00:09:20] Marie: Includes working with compliance teams, et cetera, to try and help get a message across. Um, and back then, I mean, humor was my thing, right? Everything, uh, every idea I had was all about, "Hey, we could do this, it'd be super funny," or, "It'd be really engaging." Um, and there was no appetite for it.

[00:09:38] Kelly Leonard: Sure. Yeah

[00:09:39] Marie: as too risky or not serious enough, and we can't make fun of this, and we can't do that. And there's a delicate, there's a delicate line between being funny and being, uh, careless or negligent. so you can't... And I find I've watched some of the shorts that you've got on YouTube. I think there's The Passion Within I've watched, and there's the one about [00:10:00] the superpowers

[00:10:01] Kelly Leonard: Mm-hmm. Yeah. It, it helps when you have science and data on your side.

[00:10:06] Marie: Correct.

[00:10:07] Kelly Leonard: And so I think this is, this is the thing. When, when, when you're ... The world has sort of come to us with regard to that, that, and recognizing that salience is what's important, and there's nothing more salient than a laugh. Um, but pe- people get that.

[00:10:22] Kelly Leonard: And then, and then, you know, because so many companies have signed up for this, that, that's the other thing, is like once you get your foot in, in the door, that makes it a lot easier to go forward. But it, it's, you still see those objections today. It's just kind of funny given the fact that the most expensive ad spots that exist in the, at the least in the US market, but I bet it's international as well- Mm-hmm

[00:10:49] Kelly Leonard: um, are mostly made up of comedic-based ads, if you think about during the Super Bowl. So they're not often very funny 'cause they're not written by, like, comedians, but they, you know, but they are trying to be funny, [00:11:00]right? Yeah. So I th- I think it's important to sort of look at, like, well, where, where are people spending the money and, and where- Mm-hmm

[00:11:06] Kelly Leonard: are we grabbing their, their attention?

[00:11:09] Marie: Yeah,

[00:11:09] Kelly Leonard: Yeah.

[00:11:10] Marie: incredible. Um, in your book, Yes, And... Actually, before we talk about your

[00:11:15] Kelly Leonard: Yeah.

[00:11:16] Marie: Yes, And, can you explain to the

[00:11:18] Kelly Leonard: Sure

[00:11:19] Marie: the premise of, what's the basis of Yes, And?

[00:11:23] Kelly Leonard: So when we sold the book originally to Harper Collins, it was called The Revolution Will Be Improvised, uh, which was a play on a Gil Scott-Heron, uh, song, who was a wonderful artist. And we... And that was gonna be the title, and they had an idea that the marketing team that was coming to Chicago for a conference should go through a Second City improv workshop.

[00:11:46] Kelly Leonard: So we, we took the whole marketing team at Harper Collins through a workshop, and one of the exercises we almost always teach early is this yes, and exercise. And the exercise is very simple. We have, we, we, we make a premise. So, so [00:12:00] we sort of say, "Hey, today was so amazing, uh, we're gonna get together in a year and have a reunion party, everyone who's in this room together.

[00:12:06] Kelly Leonard: So we're gonna pair up people. You're Person A, you're Person B. Person A, you're gonna pitch your ideas for the party to Person B. Person B, in this first round, you're just gonna say no to every idea. Let's see what happens. Do that for about a minute." Predictable results, not very fun. Um, sometimes it's more fun for the person saying no, but that's also them being mean.

[00:12:24] Kelly Leonard: Uh, so then we have them reverse, and Person B pitches. And in the second round we have them yes, but every idea. And what's interesting about that is they do it for about a minute, about half the room kind of thinks that's better, half the room thinks it's worse, and we're like, "Yeah, you heard a yes, but...

[00:12:38] Kelly Leonard: And that was no with a top hat. That was, that was the most passive-aggressive yes you could have gotten." And in the third round, everyone yes, ands each other's ideas, and that's funnier. That's amazing. We're suddenly having sushi on the moon at this party with Taylor Swift playing. And what we, what we sort of explain is that yes, and is used at Second City as a [00:13:00] way to get to an abundant amount of ideas.

[00:13:02] Kelly Leonard: What, what we know is when we're creating a sketch comedy show over a 12-week period, uh, the first four weeks, all yes, and. We put up every idea, no matter how crazy or dumb it might seem, because honestly, novel ideas don't necessarily look sane 'cause they are novel. They haven't been done before. So that yes, and period is hugely important.

[00:13:23] Kelly Leonard: Plenty of space for no after that. That's all, you know, pair- pairing down. And, and what we say to folks in these various companies is y- you're not putting on a comedy show, but you are in a place where you're looking for good ideas and looking for new ideas, and if you don't create spaces for yes, and, you are doing a disservice if you seek to be creative and innovative.

[00:13:48] Kelly Leonard: Um- Mm-hmm ... and so when the HarperCollins people marketing team went through this, like, "That's the title of your book." I mean, they, they were like, "You are titling it Yes, And." God thank them for doing this because, like, [00:14:00] I- I know ... I didn't invent the term, but, you know, m- my book is certainly the thing that popularized it outside of improv circles, and, and it's, and it's this, it's a bumper sticker.

[00:14:10] Kelly Leonard: It's sticky. Um, and, and that makes sense, and there's way more depth beyond yes, and, and, you know, if I ever get around to writing the follow-up, we'll, we'll talk about that. But, you know, it is an important starting place for someone who is looking to understand why improv methodology might make sense for someone in, in a job.

[00:14:32] Kelly Leonard: Mm-hmm.

[00:14:36] Marie: an idea, not judge it,

[00:14:38] Kelly Leonard: And then

[00:14:39] Marie: it, and you add to it

[00:14:41] Kelly Leonard: Yep, you build, you build upon it. Uh, my, my wife likes to... My wife Anne, who is a longtime Second City director and teacher, uh, and writer, she prefers the term explore and heighten, um, because that's, that's what you're doing. You, you are exploring together. You're heightening together.

[00:14:56] Kelly Leonard: You're seeing where these things can lead, and you're never denying the reality of the [00:15:00] person across from you. And why this is radically important is it's simple validation, and when, when you wanna think, when you think about where we let each other down, um, when we think about how to be the best partner we can be, sometimes you just validate.

[00:15:22] Kelly Leonard: You just val- You see the person across from you. Their reality is their reality. You acknowledge it. You appreciate it. Now, in, in improv, you build upon it, but, but without ever denying that reality. And I think if you monitor yourself throughout a day as a teammate, as a partner, as a parent, you are likely not yes, and-ing.

[00:15:45] Kelly Leonard: You are likely not validating. Not out of evil intent, um, but simply it's an easier default to say no, and behavioral economists were onto this. They, they, they know that, you know, people's default is [00:16:00] to say no or do nothing. Um, status quo bias. Um, and so y- yes, and is a practice that allows you to flex that other muscle which is one of curiosity and one of inquiry and one of validation.

[00:16:17] Marie: And it's

[00:16:17] Marie: not easy to do.

[00:16:18] Kelly Leonard: No, it isn't.

[00:16:19] Marie: It's actually not easy to do. I did an improv class,

[00:16:22] Kelly Leonard: Угу

[00:16:23] Marie: or a course, um, and I found it very difficult

[00:16:27] Kelly Leonard: Угу

[00:16:28] Marie: of my thinking, trusting myself, let go of judgment,

[00:16:34] Marie: and to just roll with something and build on it. It's a real skill.

[00:16:38] Kelly Leonard: Yeah

[00:16:41] Marie: in your book, you talk about working with, uh, a major league basketball team

[00:16:46] Kelly Leonard: Uh, yeah, or basically baseball. Yeah

[00:16:49] Marie: Baseball team, correct. And they were young, new, coming up, new professionals. How on earth, why did they need yes and, and what did that do for them?

[00:16:59] Kelly Leonard: [00:17:00]Um, I'm gonna,

[00:17:01] Marie: on?

[00:17:01] Kelly Leonard: uh, uh, I'm actually gonna s- say that we actually did less yes and with them, and more strategic deflection, uh, and, and more practice in public speaking. Um, th- these were the really high-paid rookies. So people were coming to the league who maybe didn't come from money, uh, and were suddenly gonna have a lot of money.

[00:17:25] Kelly Leonard: And what Major League Baseball discovered was their normal, um, consultants that they were normally using for this, which are sort of like McKinsey, Deloitte-type consultants, were not reaching the 19-year-olds, the 20-year-olds, the Dominicans. I mean, it was just like they, they, they shared nothing with the older middle-aged white guy in a suit.

[00:17:48] Kelly Leonard: A diverse Second City ensemble who were all... By the way, these were all performers who were also facilitators, so they had s- they'd seen us perform and make them laugh. So we got buy-in. We got [00:18:00] buy-in from, from the players, and then when we started taking them through these very specifically designed workshops, a lot were about, all right, how do you pivot?

[00:18:11] Kelly Leonard: How do you be agile, uh, in a conversation with a family member who wants money, uh, a media person who wants you to say something bad? Um, and so really w- we did a s- a ton of different exercises which were just allowing them to practice communication skills, uh, in the same way that they would practice hitting and throwing a ball.

[00:18:32] Kelly Leonard: Like when, when you... A- and you probably... I don't know if your sport is football, soccer. I am a huge soccer fan, since... So, so, and I was a player as well. So o- one of the things I think people think we do is role-playing. We don't. We rarely do role-playing. What, what we do is we focus on the skills, just like you would when you learn football, you know?

[00:18:53] Kelly Leonard: So, so, you know, you're doing... The, the greatest players in the world are, are learning how to [00:19:00] trap a ball. They're learning how to kick a ball in different ways. They're often in very confined spaces. So a lot of these exercises are very little phenomena that we're having people work on with regard to what they're hearing, what they're saying, how they're saying it, what their status is in, in a room.

[00:19:16] Kelly Leonard: This is where the theater stuff comes in incredibly important, is like the way you literally are standing at a podium can affect how people are hearing things. If, if you have incredible posture and you're d- exhibiting these high-status behaviors, you can get away with saying a lot of bullshit, uh, that people will let you get away with.

[00:19:36] Kelly Leonard: So that was stuff that we started doing with Major League Baseball. God, this is decades ago. And, and- Mm ... and we work with a lot of professional s- uh, sports teams now. We're working with the NHL. We have done stuff with the NBA.

[00:19:47] Marie: similar

[00:19:48] Kelly Leonard: Similar things?

[00:19:49] Marie: for similar

[00:19:49] Kelly Leonard: All, all different. All different. Um, a- a- a- again, the, the... Uh, people hate it when I say this, but, um, it is- It's a, it seems [00:20:00]inevitable that people in their various industries think that their issues are simply germane to their in- industries.

[00:20:08] Kelly Leonard: I have no proof that that is true ever. Uh, I think their issues are the human condition, humans working with other humans, and the things that happen therein, and that's it. We can, we can apply a different kind of lens. The debrief where they get to talk about how th- these factors play out is all important, but really it is the, the skills of human communication, and often human miscommunication, which are germane to all of us, whether you're working at Second City, whether you're working for, um, y- you know, Tot- Tottenham Hotspur, m- my team that's terrible, um, or or a bank.

[00:20:50] Kelly Leonard: You know? Like, we're, we're all dealing with this, with, with the, with the stuff, that same stuff

[00:20:56] Marie: There's this, there's a lot of talk here anyway [00:21:00] in HR media, in biz- in recr- you know, when we're talking about recruitment and culture, about this big kind of generational divide,

[00:21:08] Kelly Leonard: Mm-hmm.

[00:21:08] Marie: between the Gen Zs and the Boomers or the Millennials and the different ways that we communicate. Have you been seeing that in the US, has, and has that been a reason for more work in corporates?

[00:21:21] Kelly Leonard: Yeah. So huge. I, I, I would've s- I, I would g- probably say the last, uh, certainly COVID, since COVID, uh, maybe even a little bit before, that is a big reason we get hired, um, to come in. And, and our work is very effective at, uh, addressing those issues, which I will go on the record as saying are non-issues. Um, every generation has felt the next generation coming up is soft since we understood what generations were and are.

[00:21:54] Kelly Leonard: There is just no research to actually suggest that there [00:22:00] are these giant, uh, uh, differences in, in, in behavior. There is where the generation starts, um, that is different, usually in a technology kind of way from another generation.

[00:22:11] Marie: Yep

[00:22:12] Kelly Leonard: and I, uh, m- mostly it is the, the things I was already talking about, which are like, no, they just communicate a little bit differently.

[00:22:20] Kelly Leonard: You know? And, and, and words change, and pe- and, and sometimes older generations have a hard time dealing with the fact that words change. Again, always has been true. You wanna look at the,

[00:22:30] Marie: Very

[00:22:30] Kelly Leonard: the... My, my, my wife was doing some research, uh, 'cause she runs a, a comedy major, the first ever major in comedy, writing, and performance at Columbia College here in Chicago.

[00:22:40] Kelly Leonard: And there was a scene that Adam McKay, uh, who's the, the well-known director, and Scott Adsit, who was on 30 Rock, uh, they did, they did at Second City called Gump. And, uh, it was, we put it up in the 1950- in, in, in the, uh, mid-'90s, and basically Adam was an HR [00:23:00] director, Scott was a VP who'd gotten his job from nepotism, and the results of this personality test showed, and the word, the word they used at the time was retarded.

[00:23:10] Kelly Leonard: Um, and no one balked at us using that term in 1995. By 2000, 2001, we couldn't do it on colleges, and even a couple years later we couldn't, couldn't do it, do it here. And Anne, my wife, was curious of like, what, what was the deal with that? And she started researching terms that were used, uh, at various times like that, and almost always it was a, it was at once, it was a scientific term until someone turned it into a slur.

[00:23:43] Kelly Leonard: And this, the, the, uh, I don't wanna say all the words, but the, you know what they are. You go backwards in time, and they were the science term, they got turned into a slur, and then they had to change the term. So this, this idea that language changes and updates and morphs [00:24:00] is, is, is always been, been true.

[00:24:02] Kelly Leonard: Um, there's always been perceived, uh, uh, differences between the, the generations. But, but the things that are constant, um, are things like good relationships, uh, people wanting to, uh, uh, appear competent, um, people wanting to connect, people feeling seen. And the wonderful thing about an improvisational practice is all those levers are the ones that are being pressed, uh, to, to be a good ensemble, to be a good improvisational ensemble.

[00:24:39] Kelly Leonard: Before they go out on stage every single night, our main stage cast taps each other on the back and says, "I got your back." That is a very powerful pro-social act that if you were in a team that did that every day, I guarantee you it would increase your team efficacy. Guaranteed[00:25:00]

[00:25:00] Marie: What do you think about gen- when we think about the generational divide, there's a lot of training, we talk to a lot of leaders

[00:25:08] Kelly Leonard: Угу

[00:25:09] Marie: be talking to your team, and this is what your team likes, et cetera. Is there also a responsibility the younger generation that's coming through to equally invest in their skills and say, "Well, no, I also need to learn how to listen and how to understand,"

[00:25:26] Kelly Leonard: Yeah

[00:25:27] Marie: and meet, in order to kind of meet the, the, the manager or the rest of the team halfway?

[00:25:34] Marie: Not even halfway, I think just to demonstrate an openness

[00:25:38] Kelly Leonard: We all have to see each other. That's, it's, it's not, it's

[00:25:40] Marie: Y-

[00:25:40] Kelly Leonard: it's not a one-way street. It's a, it is a, is an eight, it's a two-way street. So one of the, one of the exercises I love that we often do, uh, early in our workshops is called Red Ball, and that's when we get, uh, everyone in a group and w- the, the teacher facilitator holds [00:26:00] up an imaginary ball and says, "We're gonna throw around this, this red ball."

[00:26:05] Kelly Leonard: And, and, and we do it in, in the group, and, and people start discovering, well, what makes it effective? Well, making eye contact and, and someone being ready for it or not. But then we introduce a blue ball, and the blue ball gets thrown around. And then suddenly an anvil comes in, and, and the chaos that sort of insu- i- ensues as people are trying to keep track of this, literally to try to just, like, play the game right, is such a telling lesson to how our days are.

[00:26:30] Kelly Leonard: So our days are spent getting messages through Slack or WhatsApp or email or text or LinkedIn or Facebook. And I'm saying or, it should, it's and. All these different, the, it, you know, and someone dropping by the office, and our brains aren't built to do this. So the crisis in our workplaces is not generational.

[00:26:53] Kelly Leonard: The crisis is we have not created good norms around how to use technology and how to [00:27:00] use communication in offices. I, uh, I've met a couple people in these conversations, these companies who are so brilliant in terms of like, "Hey, if we have Teams, but Teams is only gonna be used if there's an emergency."

[00:27:12] Kelly Leonard: And it's like, great, now I know that if I see something on Teams, I will drop everything because the minute I drop something, I'm distracted from the other thing I'm doing. We have to create these, these new norms, and these exercises help illustrate, uh, the problem, the challenge, and often inspire people to, like, act, which I love.

[00:27:32] Marie: How long do your programs run for?

[00:27:35] Kelly Leonard: All different now because it, it depends. I mean, it, standard used to be three-hour sessions, sometimes six-hour sessions with breaks. Um, increasingly we're working with, let's say it's nurses or other people who just don't have that time, so we're like, "Great, let's set up, uh, 30 minutes to work on this this week, and we'll do 30 minutes again next week."

[00:27:55] Kelly Leonard: So they're highly tailored because they need to be based on, [00:28:00]uh, are these teams together all the time? Are they apart all the time? We just did, uh, a whole day of work for Nielsen-Massey, the vanilla company, 160-year-old business, completely remote. This is the only time they all get together. And so they're very invested in what they do live in that room.

[00:28:21] Kelly Leonard: So they had me lead off the day with an interactive keynote that I did at the Chicago Athletical, uh, the Chicago Athletic Club, which is a very cool, uh, building on Michigan Avenue, and we were on the basketball court. And the whole idea was they wanted them playing, and they wanted them, you know, sort of building the, the, the sort of the ears and the eyes of meaning and purpose and trust.

[00:28:42] Kelly Leonard: And then I handed it over to two of our facilitators who then went and, uh, a deep dive in term, in terms of workshop for them. Uh, and, and we had a whole full half day with them, which they started with that to then go into their meetings 'cause they felt if they, you know, went in having flexed all those muscles, it would be [00:29:00] way more, a way more effective use of in-person time, which they just rarely get.

[00:29:05] Marie: And it's fun. I feel like if you're

[00:29:07] Marie: gonna get together training, this is the kind of training

[00:29:11] Kelly Leonard: Yeah

[00:29:13] Marie: What I find really interesting about the work that Second City does, I mean, it makes sense. You guys have been doing it for so long that, you know, all your research and experience has just com- compounded. Um, but I think one would think that if they were going to be doing a training course through an improv theater, it's th- you're just playing a bunch of theater games

[00:29:33] Kelly Leonard: Угу

[00:29:34] Marie: confident on your feet and how to sp- how to project your voice. And one of the things that I see a lot of here is that expectation that if I'm gonna do some kind of training that's gonna help me communicate or collaborate better, uh, and I'm gonna do it, um, you know, through anyone really, a big focus of that is gonna be just on how I use my voice, how I can be, use my body a little bit more. I know what I teach is a lot more than that, [00:30:00] and it's interesting that for you guys, you come from that theater background. But actually, there's so much behavioral science,

[00:30:08] Marie: communication theory. It's just, it's rich

[00:30:12] Kelly Leonard: Yeah. Uh, it's funny 'cause the, the Nielsen Massey workshop, I ended up writing a piece for Forbes, it hasn't come out yet, um, about the fact that w- they, they were very interested in play, which is a very rare thing for a client to say to us. In fact, although we know we're doing play, we can't sell play. We can't sell it.

[00:30:32] Kelly Leonard: So we called improvisation. And there's great science to back up this whole idea that play is a way we learn. It is a way we learn, but, but corp- corporations don't wanna buy it. And then also, w- so one of the projects I'm most proud that I work on is with the Policing Leadership Academy,

[00:30:48] Marie: உம்

[00:30:49] Kelly Leonard: the University of Chicago Crime Lab.

[00:30:50] Kelly Leonard: So we work twice a year with these cohorts of, of senior, um, uh, law enforcement, uh, teaching them a lot of, a lot of different, the improv [00:31:00]exercise we've talked about, a lot of storytelling, so that's where we do get into some of the other theater stuff. However, what we found out is they had done some, uh, workshops with sort of theater-y people before and hated them.

[00:31:13] Kelly Leonard: They did not wanna be a flower.

[00:31:15] Marie: Why?

[00:31:16] Kelly Leonard: they didn't-

[00:31:16] Marie: see. You

[00:31:17] Kelly Leonard: They'll, they, they, they're like... And so, so we really went in and it'd be like, "Yeah, we're theater people, but we're actually here to talk about life and death stuff." Because, you know, we've, we've worked with, uh, at Quantico with the FBI hostage negotiating, uh, folks.

[00:31:32] Kelly Leonard: So w- we, we're able to sort of talk a little bit about our bona fides. And then also we just get down to business. We're like, "Okay, we're gonna do this exercise. We're gonna tell you why we think it's important. You tell us what y- what you learned from it, and then, and then next." You know? And then, and some storytelling, and they really loved...

[00:31:49] Kelly Leonard: W- we, we had not... The v- the very first session that we did, we weren't planning on doing some storytelling stuff. And my partner Tyler Dean Kempf, who I do this with, and, and our [00:32:00] colleague Tree Branch, that's her real name. Um, so Tyler, uh, they, they asked something about storytelling and he has taught at Columbia College in TV and film, and he's like, "All right, let me, I'm gonna take you through like Wizard of Oz and sh- show you these tropes."

[00:32:13] Kelly Leonard: And they loved it. And it was like, okay, so this, this makes sense. We, we add this in and then we add sort of the improv comedy elements, uh, that, that we've got. One, one of the exercises they love that we do is called 60-30-10, and it's a storytelling exercise, but it can be used for more than that. But we have, uh, a person tell their accomplishment to someone else in 60 seconds.

[00:32:36] Kelly Leonard: We have that person repeat back to them what they heard in 30 seconds, and that person has to repeat what that accomplish- accomplishment was in 10 seconds and reverse. And it is a way, and they, they get this immediately 'cause sometimes y- uh, 60 seconds is a lot of time and, and people don't know that.

[00:32:53] Kelly Leonard: It's like, no, no, no, a minute, like talking for a minute is, is a lot of time. So y- that's a gift you have occasionally. [00:33:00] Often for these cops, they have 10 seconds to get across the thing that's, that's important. So the ability to practice that, um, w- with a partner, they've never had that. And these are people who are like, this is life and death stuff that relies on the words coming out of their mouths and the, and the words coming into their ears.

[00:33:18] Kelly Leonard: So they get it and, and you know, it's, it's just really, it's very gratifying to me. And if you had told 16-year-old Kelly that he would really love working with a bunch of cops, I would've been like, "You're outta your mind. This is not my scene."

[00:33:36] Kelly Leonard: Um-

[00:33:36] Marie: the question, what was 16-year-old Kelly like, and why would he be

[00:33:40] Kelly Leonard: Oh, c- c-

[00:33:42] Marie: I wanna know

[00:33:43] Kelly Leonard: yeah, pot wasn't legal back then. Six-year-old Kelly was getting, you know, nabbed. Uh, uh, never arrested exactly, but certainly held, uh, for, for that. I was very anti-authority. I was so pro-individual. And it's, and this is such an interesting thing. I just turned 60 this year, [00:34:00] and you know what I realized after 60 years?

[00:34:03] Kelly Leonard: None of us are doing this alone. I, I, I, I so honor people's individualism, however, we are a group. Even when we're alone, we're not in this world because we did something by ourselves. There's a lot of people who, who got us into this world and, and, and, and we, and we've hopefully helped, helped some other people.

[00:34:25] Kelly Leonard: And so the ability, the idea that I can now work with these authority figures who I used to either fear or disrespect, and realize they're just human beings too, and so many of them, you know, uh, really love what we bring to the table and, and want to do well. There's, there's this one cop, an African American guy, older guy, I think he maybe even a little bit...

[00:34:47] Kelly Leonard: I don't know if he's older than me, but we're roughly the same age. And he, he's like, I to- he raised his hand at the end of the session. He goes, "I understand how this is gonna help him work, and I want you to know I'm appreciative of that, but I think it's even gonna help me more in my marriage, and I [00:35:00]want to let you know how important that is to me."

[00:35:02] Kelly Leonard: And I was like, "Wow." That, that felt like we were doing God's work

[00:35:06] Marie: Yeah. It's like emotional intelligence work. So

[00:35:09] Kelly Leonard: Yeah

[00:35:09] Marie: spoke, I've since become certified in emotional

[00:35:12] Kelly Leonard: Oh, cool

[00:35:13] Marie: and development. Um, but I also used to co-host the podcast AI at Work, and used to do a lot of work with, um, one of the world's leading AI companies called Genos International.

[00:35:23] Kelly Leonard: Угу

[00:35:25] Marie: heartwarming and fascinating things is that here they are, they're going in to help major organizations build connection and

[00:35:33] Kelly Leonard: Угу

[00:35:35] Marie: And the feedback they'd get was, "Oh my God, I just- my relationship with my daughter has changed."

[00:35:40] Kelly Leonard: Yeah, that's right

[00:35:41] Marie: is better, work is doing great, and they would see, their research would often show increase in profit or retention or innovation or whatever it might be. but the really cool stuff was people coming back and saying, "Well, I can connect with my daughter,"

[00:35:56] Kelly Leonard: Yeah. Yeah

[00:35:57] Marie: better with my wife," or, "I take better care of [00:36:00] my own health now."

[00:36:01] Kelly Leonard: Yeah. I mean, that, that's so been true in my experience. I think I, I'm a better parent for it, I'm a better spouse for it, I'm a better friend, uh, for it. I'm a better human even when I go to the coffee shop in the morning in terms of my ability to look someone in the eye and smile at them and try to make a little, uh, a little moment of connection.

[00:36:21] Kelly Leonard: Um, you know, we, we, we did so much work with the behavioral science community, especially at the University of Chicago, and Nick Epley is one of the scientists there, and he's got a couple terrific books. Um, and a lot of his work is on how human beings don't self-disclose, uh, when if they did, um, good things are gonna happen.

[00:36:44] Kelly Leonard: Um, because a lot of people mirror. Uh, but also just those, that sh- those sharings of, of personal things get people to connect more quickly. And so we devised exercises b- exercises based on this. But also it's something that I think I al- I did, I [00:37:00] pretty much already did, uh, but I supersized it based on becoming familiar with Nick's, Nick's work.

[00:37:06] Kelly Leonard: So I make sure in any, especially when I'm meeting someone for the first time, is just dropping two or three things about myself that aren't necessarily obvious. Um, and that, and that gets repaid, and it just ma- it, it, it's, y- you jump from small talk to deep talk far more quickly. Small talk's good. Small talk is, is, is needed sometimes to sort of scale up.

[00:37:29] Kelly Leonard: But I, I don't know. Again, at 60, I don't, I don't have a lot of times for, you know, thin conversations. I wanna, I wanna have more thick conversations

[00:37:39] Marie: You do a lot of public speaking.

[00:37:41] Kelly Leonard: Yeah。

[00:37:42] Marie: I see you post about it all the time, and you are an incredible storyteller. I think not only is it your incredible energy, but your stories, the content of your communication is rich.

[00:37:54] Marie: You use awesome examples. You just, you're fabulous, right?

[00:37:59] Kelly Leonard: Thank you

[00:37:59] Marie: [00:38:00]still get nervous when you public speak?

[00:38:02] Marie: When

[00:38:02] Kelly Leonard: Oh, yeah

[00:38:03] Marie: nervous?

[00:38:04] Kelly Leonard: Oh, no, every, every time. Um, Alison Wood Brooks from Harvard, who's a friend of, uh, my wife and I, we... I had met her kind of at the beginning of my speaking career. I, I've always done public speaking 'cause I've been in senior positions from an early point in life, and my dad was a radio/TV guy.

[00:38:22] Kelly Leonard: So it, it, it's... The, the st- the stage was something I was usually pretty comfortable with. But the idea of like for 45 minutes or an hour getting up in, in front of people was, was a little daunting at first. And I remember Alison, who ba- she has a book called Talk, she... It's the science of how people talk.

[00:38:38] Kelly Leonard: She, she was like, "Say out loud you're excited as opposed to saying out loud you're nervous." And it, it works. It works really well. But the idea behind it, of course, is that, um, you know, it's adrenaline. We're... You, you actually do want that kind of energy to propel your convers- your, your, the conversation you're about to [00:39:00] have or the speech you're about to give, just like someone on, on a sporting team is gonna, gonna want that as well.

[00:39:05] Kelly Leonard: What you don't want it to do is veer into nervousness and, and, and that sort of thing. So no, I, I, I get what other people call butterflies. I'll get clammy on, on my hands, and so I do something about it, right?

[00:39:17] Marie: Mm-hmm. So what do

[00:39:18] Kelly Leonard: pr-

[00:39:18] Marie: What are your practices?

[00:39:20] Kelly Leonard: in addition to saying I'm excited, which I do out loud,

[00:39:22] Kelly Leonard: um, I make sure I've got some physical activity that I've done before I get up there.

[00:39:27] Kelly Leonard: I practice with, you know, my voice. I, I don't, I never walk into... I do a lot of early morning ones, right? So I just know I have to talk for easily 20 minutes before I do anything. So s- some unfortunate cab driver has a very long conversation with me, um, on, on my way to the gig. Um, and then I will also make sure that I have, once I get to the venue, if someone's greeting me, I ask them a lot of questions, and I just get myself sort of physically sort of, uh, you know, hyped up.

[00:39:58] Kelly Leonard: And, and then [00:40:00] I don't... Nothing I do is scripted, uh, because I've tried that and it doesn't work well for me. Um, but I, but I have my sort of, my list of stories that I can draw on, and- A plan. Mm-hmm

[00:40:13] Marie: You have a

[00:40:13] Kelly Leonard: me, j- Well, yeah, I got a bit of a plan and I've got beats. Yeah. But

[00:40:17] Kelly Leonard: I, but I also let the conversation, you know, happen the way it does 'cause, uh, 'cause, you know, I r- I read so much.

[00:40:23] Kelly Leonard: Uh, like I, I, I host our podcast here and, um, I probably read about two to three books a week. Um, and, and these are not improv books. They're, you know, other books. But they're all, they're... Almost everything ties to, to our work. And so I wanna draw from that stuff and, and, you know, f- use, use other people's, uh, in- insights.

[00:40:44] Kelly Leonard: Here's, here's one. Like I, I was interviewing Morgan Housel, who's a terrific, uh... He writes about money, uh, but more than that. And he has a line in his last book, and it wasn't even his, it was his brother-in-law, who said to him, [00:41:00]"Everyone's behavior makes sense if you have enough information."

[00:41:07] Kelly Leonard: I mean, I have never heard those words put together in that way, and that is one of the most profound lines. Yeah. Everyone's behavior makes sense- Yeah ... if you have enough information. And I, I don't, I've n- So I've been using that lately as just sort of like, "Hey, a- the, apropos of nothing, you need to know this line."

[00:41:28] Kelly Leonard: And the tie to improv is this sort of curiosity mindset, that if you go in with a non-judgmental mindset into your particular improvisation, which could be a conversation, whatever, um, much better place to be. Uh, mu- you're much more apt to actually understand what is being said really. Um, yeah, just great.

[00:41:54] Marie: It takes confidence to do that, a lot of confidence to kind of go in there and just listen [00:42:00]and have to

[00:42:00] Kelly Leonard: Yeah. Mm-hmm

[00:42:02] Marie: if you're truly listening, the outcome of that conversation or what you're bringing to it may be very different to what you thought you would,

[00:42:10] Kelly Leonard: Yeah. Yep

[00:42:12] Marie: in if it's, you know, I don't know, maybe you're pulling someone up on their performance and you have, "Right, I'm gonna tell them this.

[00:42:17] Marie: They're gonna be on a performance plan. This is what I'm gonna expect." But then you go in, non-judgmental to listen, and they're having a really tough time.

[00:42:24] Kelly Leonard: Right, right

[00:42:25] Marie: you're genuinely listening, then that plan is no longer fit for purpose in that moment,

[00:42:31] Kelly Leonard: Yeah, that's right. That... Yeah, yeah. So, so th- this is, this is... Assume you're wrong. Just assume you're wrong and, and, and, and make discoveries. And, and that, again, a discovery mindset, um, allows you to witness the world in a very different way, um, and one that makes you open to new truths, uh, unusual truths, [00:43:00] um, opportunities.

[00:43:01] Kelly Leonard: I mean, we always, we always say s- you know, see all obstacles as gifts in improvisation, because something weird happens on stage, use it. Uh, Rick Thomas is a former teacher and performer here, and I remember Colbert, Stephen Colbert used to love this phrase that he had, which is, "You need to learn to fall into the crack in the game."

[00:43:22] Kelly Leonard: And for, for Rick and for Stephen, that, that, that sort of meant like, hey, when something, something seemingly, you know, like a little scary, unusual mistake, whatever, go towards it. And, and 'cause you're g- you potentially can find riches there. Not always. Sometimes it's just a crack where you're gonna fall and hurt yourself.

[00:43:45] Kelly Leonard: But f- but for the most part, you know, uh, we're, we're not. And, and who, who knows what, what's there to be discovered?

[00:43:53] Marie: So true. And you know what, um, another bit of work that you did that I loved was the work you did with Radical Candor.

[00:43:58] Kelly Leonard: Yeah. Yeah

[00:43:59] Marie: [00:44:00]book is... I love... Yes, you know what? Since I came across and I found you on LinkedIn and started following what you were doing, and then I read your book, and then I kept researching, and then I discovered the work that, um,

[00:44:12] Kelly Leonard: Kim Scott.

[00:44:12] Marie: with Kim Scott

[00:44:14] Kelly Leonard: Yeah

[00:44:14] Marie: the Radical Candor series.

[00:44:16] Marie: Is that what it's called? The content s- I know that's the name of her book. The

[00:44:19] Kelly Leonard: Yep.

[00:44:19] Marie: you created with her

[00:44:21] Kelly Leonard: Oh, it's called, uh, Impro- uh, Improvising Radical Candor

[00:44:24] Marie: Improvi- I mean, what a brilliant idea. And how she's incredibly generous. To anyone listening, please go check out, um, Radical Candor because she gives you so many different resources to help you have really honest conversations with people. And the content that you guys created is just hilarious. It's like a mini, it's like a miniseries?

[00:44:47] Kelly Leonard: Yeah, it's like a mini TV series. Yeah, I s- c- so Kim was a very early guest on the podcast. I, I'd heard about her book, but I didn't know her, and we had such a wonderful conversation that she's [00:45:00] like, "We should talk more." And we started having sort of regular calls, and then she came for a visit to Chicago with a member of her team, and we hung out for a couple of days, had meals, and workshopped some ideas.

[00:45:14] Kelly Leonard: And then we came out to her home in California for a week, al- almost a full week, and developed this idea, you know, j- just on, on sheets of paper and, and ended up creating some live workshops that led to the series, uh, which debuted, uh, in March just as we all went into COVID lockdown. Uh, so it, it, it was n- not the best timing.

[00:45:37] Kelly Leonard: The series actually ended up doing pretty well, all, all things considered. Uh, but yeah, she, she's a great friend and, and the thing I love about Kim and her, the way she thinks structurally is so smart. Um, these, these Radical Candor quadrants that, that, that we all sort of operate on differently. Like, we're never static.

[00:45:57] Kelly Leonard: You're always in some aspect of these, these quadrants, [00:46:00] but, but those, the behaviors that exist therein, again, can all be practiced, and that, that's why the sort of chocolate-peanut butter mashup of Radical Candor and Second City improv really worked well.

[00:46:13] Marie: Content's not cheap create. Um, and yet content done well is a game changer terms of trying to get people to, I mean, we come back to compliance, but to, to learn something. Um, you finding that this is something... I mean, obviously the bigger guys can afford and invest in. Have you ever done it for smaller companies?

[00:46:38] Kelly Leonard: Oh yeah, we've done stuff for smaller companies. I mean, that, that, not, not normally, I mean, that, that... But we have. Um, it i- it is, it is expensive. And as, as I've started going through my brain and thinking about the clients that we've got for that stuff, they are, generally speaking, the, the bigger companies.

[00:46:56] Kelly Leonard: But there are, there are ways you can do things, [00:47:00] uh, less expensively these days. And look, I mean, you know, we live in a different world. I mean, I, I, I just got the latest iPhone, and I'm looking at the photos and video I'm able to take with it. Essentially, that's broadcast worthy. Uh, i- if not today, it, it, it would've been 10 years ago.

[00:47:21] Kelly Leonard: Um, and so more and more people can create their own content, uh, in certain kinds of ways, and I don't think people care that much about the big budget stuff. I don't think they're looking for bells and whistles. I think they're looking for f- great characters, some funny lines that carry truth. Um, uh, don't waste my time, like that's a big one.

[00:47:47] Kelly Leonard: Like, you know, g- g- get... Tell me what you gotta say. Do, do it, do it as quickly as you can. Um, uh, and so I think the, the lesson that we're all sort of learning now [00:48:00] is, um, te- technology can be our friend to aid our ability to communicate, just as it can be our enemy to get in the way of our ability to think.

[00:48:13] Kelly Leonard: And so being able to hold those two opposite truths in your mind at the same time is truly important, because we gotta be able to like know which lever to pull at what time, and especially in the AI, you know, universe that we're living in. I mean, I don't know, I don't know about you, but like the joke I seem to be telling every single week on my podcast is, I guess we're legally required to talk about AI now, 'cause every book has got that section.

[00:48:42] Marie: Yeah. Oh, I mean, it's, it, it's pervasive. It's in

[00:48:46] Kelly Leonard: Yeah.

[00:48:46] Marie: single aspect of our lives now. So it's... My kids will be driving, my 10-year-old will just look at billboards or ads. She'll go, "That's AI. I can tell that's AI created."

[00:48:58] Kelly Leonard: Mm-hmm. [00:49:00]

[00:49:00] Marie: So they're learning about it in school. We talk about it a lot at home as well.

[00:49:05] Marie: Um, but the interesting thing about AI is just how obvious it is to spot now because

[00:49:10] Marie: of how, on the type of AI, obviously it's in absolutely everything. I'm thinking of it from a perspective or a writing of view. It's just so empty.

[00:49:22] Marie: A lot of words mean nothing. And so I find that true authentic storytelling, that true, you know, you bringing some of yourself and that vulnerability, and the specifics, the examples and the stories that make your life and experience rich, that's stuff that AI can never, ever replicate

[00:49:42] Kelly Leonard: Yeah, AI. Yeah.

[00:49:43] Marie: Yet.

[00:49:44] Kelly Leonard: no, and it w-, it, it doesn't ca- AI doesn't care, first of all. Um, and it's not truly intelligent in terms of it's not making up anything n- novel or original itself. It's using, using all other kinds of material. What, what I'm finding it very useful for... Here's a good example. [00:50:00] I got s- a, a, a, a woman who lives in England, um, sent this sort of general Second City mailbox a note, an email, and she had discovered her biological father, who has long since passed away, had some association she thought with Second City, gave us her name, and there was some event, uh, uh, like a benefit that had been done here in 1990.

[00:50:23] Kelly Leonard: Uh, the name did not ring a bell. I initially did some, like, Google searches. I wasn't finding anything. And we all, the leadership team here all has Claude. So I went to Claude, and I explained wh- what she was looking for. I sort of, I gave it sort of like, "I would like to help this person, but I wanna help them with actual information that's gonna..."

[00:50:42] Kelly Leonard: And I found the benefit that we did here. I found the information, and I found out who was there. I was able to email. I haven't heard back yet. This was just, this was like three hours ago. But I- Google wasn't helping me, and Google has AI. Um, and Claude did find it, but of course what I recognized is I'd need to [00:51:00]give it a very good prompt, which also AI can't do, you know?

[00:51:04] Marie: Yeah

[00:51:05] Kelly Leonard: but, but, you know, if anything from people who've worked in improvisation will realize, like, I know how to give a good prompt. I, like, I know what I'm, what I'm doing there. Uh, but yeah, so, so I might be able to help this woman find out information about her dad, and that to me, that's a good thing

[00:51:20] Marie: Yeah, uh, there's lots of amazing uses for it, for sure. And, you know, you talk about giving it a good prompt. We have to learn how to speak to computers and technology and robots and AI, but also learn how to speak connect with humans,

[00:51:39] Kelly Leonard: Yeah.

[00:51:39] Marie: and

[00:51:40] Kelly Leonard: Right

[00:51:40] Marie: that, you know, that's something that we're losing.

[00:51:43] Marie: I think it's, you know, it's more scary. Things that we talk about, we come back to the generational divide. One of the things that some of the research here is showing us is that Gen Zs envy the way Boomers can pick up the phone

[00:51:57] Kelly Leonard: Oh, yeah,

[00:51:57] Marie: just make a

[00:51:58] Kelly Leonard: That, yeah, they don't wanna be called, [00:52:00] they don't wanna be called.

[00:52:01] Marie: right?

[00:52:02] Kelly Leonard: not wanna be called.

[00:52:03] Marie: So

[00:52:04] Kelly Leonard: That is so true. That's true one

[00:52:06] Marie: I see it all the time. I mean, when I was still in PR I'd look at a colleague and I'd say, "Well, did you call them? I haven't heard from the journalist. Did you call them?" Terror. "W- why would I ca- But I emailed." "Okay, but did you call?" And that is terrifying. So there's still a lot of... we still have to learn, all of us,

[00:52:26] Kelly Leonard: Yes

[00:52:26] Marie: It's not just the Gen Zs, all of us. We all have to... Communication is evolving. How, you know, learning how to communicate changes depending on the situation. You know, I was in a situation where my dad was in ICU, and I had to learn to communicate with a doctor that we just were like,

[00:52:44] Kelly Leonard: Yeah

[00:52:45] Marie: so vital that we connect, and we just couldn't. And what I learnt when I reflected on it was that I just was not, I did not have the capacity

[00:52:53] Kelly Leonard: Ja.

[00:52:53] Marie: to learn, right?

[00:52:54] Kelly Leonard: Ja

[00:52:55] Marie: so the, the doctor had to kind of create the environment, which the second one [00:53:00]did create the environment for me to be relaxed enough to hear what he had to say, right? So I feel like no matter what age you are, there's always room for you to learn and to grow and to build your emotional intelligence or your communication skills,

[00:53:18] Kelly Leonard: Yeah, absolutely.

[00:53:19] Marie: in the world of AI

[00:53:20] Kelly Leonard: yeah, my, my boomer wife, uh, does not wanna make phone calls either or t- or take them. That's so- Um, but I think, you know, the... And she works with college students, you know, all the time and, and it's, it's, you know, if you, if you can... Here's the thing, the, the, the thing that is crucial to a successful improvisational experience is mutual trust.

[00:53:45] Kelly Leonard: And the, the, that is the same thing that plays out in those kinds of conversations, especially in medical environments, um, because it's scary, uh, the stakes are really high, there's a lot of [00:54:00] noise, um, there's, there's a lot of lack of information on everyone's behalf 'cause if they knew how to fix the thing, they would just fix it,

[00:54:07] Marie: Yeah

[00:54:08] Kelly Leonard: and it's not clean.

[00:54:09] Kelly Leonard: And so creating an environment where the caregivers, uh, whether you be family or nurse or doctor or surgeon or whatever, can establish that sort of bed of trust, it gives you a fighting chance, uh, to, to have the, have successful conversations. Because even, even with the trust, it's gonna be hard

[00:54:31] Marie: Absolutely. Kelly, what's next for you? What's the next big project?

[00:54:37] Kelly Leonard: Um, all right, so, uh, a little bit of cat out of the bag. Uh, my wife Anne and I and our friend Dave, uh, Nussbaum, who is a professor at University of Chicago, have been working on the outline for a follow-up to the Yes And book.

[00:54:52] Marie: Amazing!

[00:54:53] Kelly Leonard: so that would be, um, looking at, um, everything that's gone on since we wrote the book, uh, [00:55:00] with a heavy, uh, dose of behavioral science, which is, which is Dave's specialty.

[00:55:04] Kelly Leonard: Um, but also recognizing that, you know, um, my wife Anne can bring in all the practices that weren't in the first book, the, the new bespoke exercises. Uh, but also the world we live in now, um, and, and how crucial it is to be able to be agile and resilient and change ready, um, in, in a future that we can't describe.

[00:55:30] Kelly Leonard: You know? The, the, w- uh, what we know, 'cause it's always been true, is a good chunk of the jobs that exist today will not exist tomorrow. Again, it's always been true. But the speed at which that is happening is unprecedented.

[00:55:44] Marie: Yeah

[00:55:45] Kelly Leonard: Yeah ... we've never experienced anything, uh, like this. So that ability to, like what you were just talking about in the hospital, the ability to self-regulate quickly, to get your breathing down, to then be ready for [00:56:00]what's next.

[00:56:00] Kelly Leonard: Um, improvisers are very good at this. Um, we have science to back it up, and we have, again, some, some, some exercises that are not well-known out of the scope of people who've taken, uh, uh, these workshops at Second City. So, um, uh, t- you know, we're working on it, and we'll send it to our agent and see what he says, and maybe in a year or two there'll be a new, a new book.

[00:56:24] Marie: Well,

[00:56:24] Kelly Leonard: Well-

[00:56:25] Marie: be waiting with bated breath. Uh, is, is Second City worried at all about AI and how it might affect entertainment?

[00:56:33] Kelly Leonard: Um, uh, yes and no. Um, yes, 'cause of course you have to understand how it's gonna affect you a- as a business. I, I d- I think actually it will only help the live theater. People are going to be craving live experiences where they can be in synchrony with other audiences. Um, that- Mm-hmm ... that I think is for sure.

[00:56:52] Kelly Leonard: Um, uh, w- as a business we've had to confront it, so, um, w- we basically started creating our sort [00:57:00] of at- guidelines, our ethics around how we use and don't use AI, and we just had a leadership meeting last week, went through a draft, uh, together, so that felt good. Um, so it's... We're still early to it. Um, this was, this was something that, that I'd, I've been talking about for a long while because the people have been coming on the podcast, but took a little while for everyone else to catch up.

[00:57:22] Kelly Leonard: But it's here now, uh, so we're, we're figuring it out along with, with the rest of y'all. Kelly, thank you

[00:57:30] Marie: for your time. Um, you have been so true to your word when you agree- agreed to do this little podcast with me, so a huge thank you from me. It means a lot. and to everyone listening, check out Yes, And before you check out part two, definitely check out, um, Kelly's podcast.

[00:57:48] Marie: It's actually brilliant. He always has really interesting guests, and I will include a link to it in, um, all of the descriptions wherever you're watching this. So huge thank you, Kelly.

[00:57:59] Kelly Leonard: Thanks, Maria. [00:58:00] Take care

[00:58:00] Marie: Lovely to chat. Bye.

[00:58:02] Kelly Leonard: Bye

[00:58:07] Marie: Thank you so much.