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Kelly Leonard: Say Yes! to Funny Business — Transcript

Read the transcript of Caitlin’s interview with Second City executive Kelly Leonard on how to improve teamwork and creativity using improvisational comedy.
by Natallia Darozhkina | Sep 27 2018

Caitlin: Welcome to Simplify! I’m Caitlin Schiller.

Ben: And I’m Ben Schuman-Stoler.

Caitlin: All right, then. I know you are excited about this episode. So take it away.

Ben: Yeah, I am actually very excited because Second City is big for me. I’m from Chicago––you know that––and Chicago is a city that’s really proud of the things it’s really proud of. And Second City, which––for people who don’t know is an improvisational comedy troupe––is one of those things that everyone from Chicago is very proud of.

Caitlin: OK, but more or less proud than deep dish pizza.

Ben: Exactly. That’s exactly the point.

Caitlin: All right. Cool. Didn’t Tina Fey come out of Second City?

Ben: Oh man, Tina Fey, Alan Alda, the Belushis, Steve Carell, Stephen Colbert, Bill Murray, Mike Myers, Joan Rivers, Amy Poehler, etc, etc, etc. And like we used to always go to the free improv on Wednesday nights. They let you in after the paid show’s finished, like an hour of free improv –– it’s amazing.

Caitlin: That’s so cool!

Ben: It’s a big thing in Chicago because you say, “Oh, I saw Stephen Colbert before he got big.” Anyway, Second City is famous for the school of improv, which they sort of invented. They’ve been running––I think it’s actually 60 years now––and they only do original works, and they’ve been sold out basically every night for 60 years. And the core of the school, the fundamental principle of the Second City improv approach is “yes, and.” So you don’t shut down a skit, you keep it going.

Caitlin: Yes, and Kelly Leonard––today’s guest––has worked at Second City for years in executive producer roles. In 2015, he wrote this book called Yes, And which describes how this concept can have meaning way beyond improv, and work in business, and help your team work as an ensemble, which is something we’ll talk about in a bit.

Ben: Yes, and in your interview you talk about the research he’s actually doing with the University of Chicago. Which is amazing because they’re learning that this “yes, and” concept actually has basis in behavioral psychology. We want to say no, we want to say “no, but.” But we have to say “yes, and.” So that’s one thing that I learned but what’s the one thing that you remember from the interview? What’s the one great thing?

Caitlin: Well, the thing that really stands out to me is this idea that you just need to be a person, and that means being willing to really see one another as human beings, allowing check-ins, really listening when someone speaking, which sounds so obvious. But sometimes isn’t, especially at work. And this thing that I learned from the interview that I really loved was this idea of the self verification theory. Which is, so I see me as clumsy, but you might not see me as clumsy. But for me to really feel seen and known by you, I need you to also see that I see me as clumsy, and respect that, and understand it, and find ways to sort of maybe adjust for the fact that that’s who I believe I am, even if you don’t, you know that about me.

Ben: And maybe not throw you the big ball.

Caitlin: Maybe not throw me the big ball or maybe like let me know first: “Caitlin, heads up.”

Ben: So let’s do it. Shall we play the interview?

Caitlin: Yeah, let’s do it.

Ben: Cool, and then we can talk about more books for anyone who’s interested in the topic afterward.

Caitlin: Awesome. See you then!

Ben: All right! See you in a bit.

Caitlin interviews Kelly Leonard

Caitlin: Hi, Kelly! Thanks so much for joining me today.

Kelly: Thanks for having me.

Caitlin: Could you please introduce yourself?

Kelly: Yeah, my name is Kelly Leonard, and I am a longtime Creative Executive for the Second City in Chicago, and my current title is the Executive Director of Insights and Applied Improvisation for The Second City. Isn’t that fancy?

Caitlin: So fancy! What does that mean? What do you do on most days?

Kelly: So, you know from 1992 to 2015, I was the Executive Vice President of Second City. And essentially I produced all the live theatrical work at Second City, so hiring all the talent, producing the shows, and in my EVP role, of course, I touched other businesses.

My book came out in 2015 that I co-wrote with Tom Yorton called Yes, And and that book is primarily about how we take our improv-based pedagogy and learning models, and bring them into businesses and organizations and for individuals to make their working lives better.

And that’s when I made the shift where I realized, you know, I’m really enjoying this new sort of path where I’m discovering adjacent science and other sort of thought leadership that connects to our work. And so I made a shift, and I didn’t know where that was going to go––classic improv, right? So, I stepped down and our owner Andrew Alexander was very kind and said to me: “Stick around, be a consultant for a year, and you can kind of figure out what you’re going to do––either build a bridge out or build a bridge back in.” And I found a bridge back in.

And so, it really revolves around a program that I co-lead at the Center for Decision Research at the Booth School of Business at the University of Chicago. And it’s called The Second Science Project. And this is pretty awesome. What we are doing is we are studying behavioral science through the lens of improvisation. So if you understand a little bit about improvisation, you know that it is rooted in human behavior. So even the idea of like “yes, and” where we talk about to make something out of nothing, when you’re improvising: you can’t say no, you have to say “yes, and.” And in behavioral economics, what they understand is that people’s default is to normally do nothing or say no.

And so literally without knowing it, we were sort of forging a path in improvisation while evidence and insights from the scientific community was sort of undergirding our work. And so now we could put these things together. So we do research, we create executive education programs, and we’re basically trying to build a body of evidence that both supports what we do, but also allows us to change what we do, should the evidence tell us otherwise.

Caitlin: You know, I just realized that everyone listening might not know what makes improv comedy different from say a stand-up comedy special that you’d see on Netflix. Could you just cover the basics of that, in case anyone doesn’t know? Thanks.

Kelly: Yeah, absolutely. Stand-up is so different from improvisation based comedy. And in fact, the stand-ups who have traditionally worked at Second City have had a harder time succeeding. And I think, this is because stand-up comedy is a solo act. It is an individual crafting their own comedy which derives from their very particular point of view with the audience. And you’re developing that over time on these stages. And this is that, you know, when people get their big Netflix special, they are usually playing small clubs for a year or so to get to the place where they can do that material. Improvisation is co-created among many individuals, which requires you to surrender often your need to be right, surrender your particular point of view. So it’s this sort of group exchange.

Caitlin: And it’s very different from the stand up experience because, as you just said, it’s a solo act. But what you have in improv comedy is this concept or this thing that’s called an ensemble. And I want to talk about that some. How is working like an ensemble different from working like, say, a team in a business, if it’s different at all?

Kelly: Yeah, I mean, we prefer the word “ensemble” because team implies competition, and ensemble is a mindset. There’s a great great phrase that Sheldon Patinkin––who was one of my early mentors here––used to say. He would say, “We all know the term ‘your team’ is as only as good as its weakest member,” and he spins that. And so he says, “At Second City, we believe in ensemble as only as good as its ability to compensate for its weakest member. Because at some point, all of us are going to be the weakest member and we are going to want to be picked up at that point.”

This is not an orientation that normal human beings have when they go to work. Their orientation is often like, “you’re good or you’re bad,” you know, “nice guys finish last.” And by the way, there’s no science to back up any of that. In fact, it is the opposite: all the data that exists––not all the data, but the majority of the data––suggests that in helping cultures, in cultures that are psychologically safe that’s where people thrive and where they innovate and where they are more productive and successful. And that’s an ensemble orientation.

So one of the things when you consider what an ensemble is is that, you know, teams come together and split apart, you get part of this team and then you’re part of that team. Ensembles never go away. So if you think about it in a orchestra, right? The Chicago Symphony Orchestra is an ensemble. No one who’s in this orchestra right now was in it a hundred years ago. But the ensemble is the same because the ensemble is a set of agreements, a set of understandings, some of which can change or morph over time. But generally, the reason the ensembles stay together is because those agreements are really strong.

So in the sense of Second City and improvisation in our ensemble, you have to make your partner look good, you have to have your partner’s back, you’ve got to be others-focused, you have to surrender the need to be right, and the list goes on.

And what we find, I mean, proof is in the pudding, right? So Second City has been around 60 some odd years, we only do original work. You can’t name for me another institution, a theatrical institution, that only does original work and is essentially sold out every night of the week for 60 years.

Caitlin: Yeah, that’s kind of amazing. If you’re getting in, say, a business that you or one of your associates walks into, is a set of individuals who are very much individuals and not accustomed to working as an ensemble, what are some of the things that you start to do to bring them together so you can even start this kind of work?

Kelly: Yeah, we play games. So, it is as simple as that: playing the games makes you an ensemble. So we’ll often start with simple listening or focus games, because the first thing we have to do is like, put the phone down. You can’t have the phone during this workshop. You’re going to have to look people in the eye, you’re going to have to talk to each other. And many people, that makes them sort of uncomfortable. But the reality is, our anticipation––there’s science for this––our anticipation of how uncomfortable these encounters are going to be is wildly out of step with what happens the minute you sort of get into it.

You know, it’s a little bit like a workout. And if it doesn’t hurt a little bit at first, you’re probably not doing it right. But you know, at the end of that workout, you always are like, “Man, I feel really good that I did this.” And you know this from conversations––if you’ve been stuck in and you’re depressed or whatever, you’re not talking to people… It’s like, you want to know how to get out of that? Go talk to someone, get with someone, you’re going to feed off of that other human.

So I’ll give you an example. So a very sort of traditional Second City workshop. We’ll come in and we’ll play a game called “Red Ball,” where we have people toss an imaginary ball to each other and have to thank each other for it. And then we’ll add in other balls and people have to keep track of it. And so suddenly you’re out of the your brain of judging and fear. You’re just trying to understand where this goddamn ball is. And so, by the end of that exercise, people sort of loosen up, like a warm-up. And then we’ll get into language and we would be like, “You know what, our knowledge of human communication is that the bulk of us actually don’t really listen to each other well. So we’re going to lead you through an exercise.”

And here’s one called “Last Word.” So two people have a conversation with each other, and the job of both parties is the last word that their partner says has to be the first word that they say. This requires you to listen to the end of a sentence. And anyone who’s listening to this, try this! Because you will realize I normally don’t listen to the end of sentences, about midway through I’m judging and figuring out what my comeback is going to be. And you can’t do this when you’re improvising on stage because the last few words could be crucial information that could change the course of anything that’s going to happen in the scene. But that’s not how we behave in the day-to-day world. So our exercise is really sort of shed a light on our kind of bad behaviors, and then give you practice in better behaviors.

Caitlin: One thing I was wondering about when I asked you about human elements in an ensemble: if everyone is acting sort of as equal as they’re all playing the same game, is there still a role for a leader in an ensemble?

Kelly: Yeah, so that’s a great question. So we have a game that speaks to the leadership principle, and it’s called “follow the follower.” So in the exercise, you have a group that is walking, almost doing a spacewalk, they’re walking around the room, and the facilitator gives one person leadership. Everyone has to stay silent, that individual though has to reveal their leadership to someone else in the group while they’re walking around and hand it off to them silently. That person needs to take the leadership and then do the same with someone else. And what this gets at is essentially––there’s an organizational theorist named Peter Drucker who talks about this––but it is that leadership is dynamic, and not static, and not hierarchical. So you know, at any given time, one of us is going to be a leader because we should be at the time with our core expertise, or our position, where we’re standing, where we’re sitting, and that changes all the time.

So in a Second City ensemble, there’s of course shared leadership within the ensemble. There’s a director, who’s outside, who at different times is stepping in because that’s their time to be a leader. There’s a producer who’s overseeing that director who does the same. And we have all these different sort of––I talked about––the sort of designed environments. And so this is one that during a Second City process to put up a show, which is like a 10 to 12 week period, the director basically tells the producer when they should come in and start looking at material. So even though technically as producer I’m the boss, I surrender my leadership to the director in the context of, I don’t want to come in and start putting my eyes on the work when it is just rough and they’re trying to figure it out, I am better served by coming in when they have something that I can then contribute to, because they’ve gone through that sort of early stage stuff. And there’s a lot of these sort of like unspoken handshakes and truths that we’ve got here at Second City that speak to the same thing of understanding that leadership is always dynamic and sometimes the role of a leader is just to get out of the way.

Caitlin: So to effectively get out of the way, so that a team or an ensemble can do its best work, that requires rescinding ego in a really radical way. Are there games to play for people to help them to do that? Because it’s so tempting to hang onto a title that feeds one’s ego.

Kelly: Oh, yeah. And there are exercises that we’ve crafted and customized that are recognizing that someone with a giant ego, who has trouble with this, tends to do this and can we put them in position of constantly having to play low status. So yeah, that’s the root of all these exercises. And in fact, you know, we’re actually doing a study right now with Charles Limb, who is a neuroscientist at the University of California San Francisco. And he in the past has studied musical improvisers using an fMRI to see what happens in the human brain when they improvise. And now he’s doing it with Second City Talent doing verbal comedic improvisation. And in both studies, what they were discovering is great improvisers, what’s happening in their brain is the part of their brain that is fear and shame based goes down. You’re literally in a different brain state when you’re improvising. And that means reducing fear and shame.

And I think, if you’re looking at the root of most bad behavior, it’s rooted in fear and shame. And it doesn’t take a genius to sort of then think about that and look at “oh, what’s happening in the world today?” You know, “why is the conversation we’re having––especially in my country––so terrible.” And you look at both ends of the political spectrum and they are awash in fear and shame.

Caitlin: So true. And this ties back into something you were talking about before, which was creating psychologically safe environments. What is that? What does that mean to you?

Kelly: So, you know, Google did this big study, and that came out as like the number one thing that you need to have effective teams is psychological safety. And so going back to our scientist friends, I’m like, “So what does this mean?” And really it means it’s a place where people feel free to fail, and there’s risk, and there’s honest authentic feedback that’s in the moment that again, where one is not trying to lead through shame or fear. You’re going to lose your job, you’re not good enough, you don’t care –– all that’s out the window. It’s much more of like clear expectations, a lot of communication, a lot of authenticity, transparency is huge, especially with regard to leadership. So why are you asking me to do the things I’m doing, if I have a good understanding of it, I can get you to where you want to be. Because you know, it’s likely that we do not have all the answers. There are so many variables in any business. And they change day to day based on new technologies and new innovations and new understandings. So if you can empower your people with an understanding of the core mission and values of your organization, the ultimate goals of what success kind of looks like, you can allow them to kind of craft their own path and have a great deal of autonomy––that’s also crucial to being psychologically safe. Give me autonomy.

And so the Second City, and I’m telling you that the Second City resonance stage, where we craft these original reviews, is a microcosm of all that is good with this stuff, because they cannot do their work unless they’re psychologically safe, they are protected from interference. And the only times we’ve had problems is when that kind of breaks down for some reason or another, but luckily mostly it hasn’t.

Caitlin: What happens when it breaks down? Or what are the things that come in that contribute to breaking down a psychologically safe space?

Kelly: So if you have someone… So let’s say, there’s always Alphas, right? Alpha-personalities, who are around that you really rely on to be kind of a loud voice in the room. If that loud voice is not… If their value system doesn’t jive what everyone else is –– that’s a problem. And what happens then is you sort of have people not telling each other the truth, and you have people keeping things from each other, or trying to hold on to power, or you know, hold on to communication. So a lot of the petty behavior that we saw in our grade school classrooms, all that stuff starts to come out and everyone who has a job knows exactly what I’m talking about, because it happens in the workplace all the time. It is so petty and small, but it is absolutely rooted in just how we tick as human beings.

And the recognition needs to be there that, you know, look, we’re going to fall into this, right? It’s not just like, you know, I equate it going to the gym. You know, you don’t go to the gym once and have a work out. I’m good, you know, those muscles they’re tuned and it’s fine.

Caitlin: Ah, I yearn for a world in which that is true, though…

Kelly: We all do. But no, you have to practice it. If you want to keep in shape, you have to do it regularly. And that is the same thing with this: I mean, I’ve often said, the person who can figure out how to turn improv into yoga is going to be a billionaire. And please, contact me, because I would like to be a part of that.

But it’s the idea that we should be practicing this kind of human-to-human interaction every day. Look, you would never assume when you came to Second City that the cast didn’t rehearse. You would never attend a sports–– whether it’s soccer, or baseball, or football, or basketball––and think that they didn’t practice. And you’re like, “why?” Well, these are peak performers and millions, if not billions, of dollars are on the line.

What is business? I mean these businesses also should employ peak performers and have billions of dollars on the line. You mean to tell me they don’t need practice but these other people do? It just it defies any sense of the reality of who we are as human beings and how the world operates.

Caitlin: Are there any tenets of improv that we can use to bring things back on track?

Kelly: Oh yeah!

Caitlin: So could you talk to me a little bit about what those might be?

Kelly: Yeah, so Yes, And Is a perfect example. If you’re in a meeting and someone is “no, but”-ing you or just no-ing you, we have a very quick path to being, “Alright. I’m not hearing a lot of “yes, and.” And that is so, you know, we wrote a book about it, you cannot deny that. So that’s a way of really sort of getting you on track. It’s interesting. Dacher Keltner is a scientist out of UC Berkeley and he’s done some study around the pro-social aspects of gossip which I find really interesting. Which is that what we’re doing when we’re gossiping is we’re pointing out that someone is breaking the rules, as we understand them. The sort of trusting bonds, they’re not playing by those rules.

So we use gossip to sort of double check that we’re right, right? They’re wrong, we’re OK. And that is a way of opening door to get that person back. And I find that very interesting because these cues that we talk about in improvisation sort of are all pointed towards a similar thing of like, we have these shared values, we’ve all agreed on them. If you’re stepping out, I can call you on your not “yes, and–ing,” I can call you on fighting for just your own thing and not sharing.

Caitlin: Is it OK if we get back to the Yes, And a little bit in the mechanics of using it? So Yes, and and improv in general, it has a lot to do with reading the signals that you’re picking up from your environment––hopefully, the psychologically safe one––but sometimes you can’t really tell. Is it ever okay to ask questions in improv?

Kelly: Oh, yeah, so that’s a great question. So many, many beginning improv teachers will tell you not to ask questions because indeed at a beginning level, that is kind of a bailout that won’t allow a scene to progress. Conversely, when you master improvisation, asking questions is a huge part of it. And what we know from science is you need to ask a lot of questions of individuals to get to their truth.

So I have a particular concept of this that we’ve dealt with in Second Science project. And it’s based on the thing called “self-verification theory.” So I think most of us feel like we want to be seen as our best selves, our prettiest selves, our smarter selves. And self-verification theory tells us something different. It tells us that 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 don’t throw me a ball. But I’m a tricky human being and I’m not going to like tell you that, that’s going to have to be ferreted out of me. And when you understand in improvisation that you have a need to be others focused. But then you understand that there’s these theories that people, you know, they’re complex. And so it’s not necessarily that I need to just see the person across from me and think that, “Well, they’re pretty so they must see themselves as pretty.” They might not! And then when you understand that, you can actually understand and see them, that’s very powerful. Because to be seen and to be heard is what human beings want.

And again I speak to our current political atmosphere. If identity isn’t at the heart of everything that we’re seeing in the world right now, that people feel unseen widely from the margins. That this is at play every day in the world that we exist. And so if we can be in an art form that practices it, that allows you to be a better seer, a better perceiver. And then also allow you to sort of give perspective to other people: can I give you the context of how to see me? That’s at the root of better human interaction. That’s the ultimate “yes, and.”

Caitlin: I wish I could show you my face right now. I have that squinched eyebrow “Awe” kind of look on my face.

Kelly: I think that’s a good thing.

Caitlin: Yeah, I think so too. I wish that more people understood that. I think, it takes most people years of therapy to understand that.

Kelly: Yeah. I’ve had free therapy at Second City for 30 years.

Caitlin: Woah, 30 years of that. Getting back to “yes, and” for a second. “Yes, and” so it is saying yes to everything that your partner suggest. Might that sound to some people who are not immersed in the practice, might that sound like just being steamrolled, like just agreeing to anything and everything? So how to establish boundaries when they are trying to practice “yes, and?”

Kelly: I think what everyone needs to know is the “and” is maybe more important than the “yes,” though you need the yes to get to the “and.” So you’re not just agreeing with the thing that was said to you. What you’re doing is you’re agreeing and adding. And in that add you are allowing the thing that you’ve just “yes-ed” to be morphed and changed together. And so what “yes, and” is really about is a way to get to an abundant amount of ideas in a shorter period of time. It’s a faster route to creativity. And by the way, that allows you room to say no a bunch. We are really into the no’s, and the edits and the eliminations, but only after we’ve allowed everyone to “yes, and” together.

So the other thing that that does, it allows a seemingly bad idea to stay and linger. Because sometimes those seemingly bad ideas end up being really cool ideas. I talked to a guy the other day, who said, “Allow yourself to put a bunch of garbage on the whiteboard.” And I’m like, “Yeah, that’s that’s a ‘yes, and.'”

So what you want to do. And look, I talk to business groups all the time about the stuff. And invariably there’s a dude in the back and it’s always a guy, who says, “If I ‘yes, and-ed’ every idea that came in my office, I’d get nothing done.” And I say, there’s two things I know about that guy: 1– he’s a fucking nightmare to work with. And 2– he’s missing the point because “yes, and” is five minutes at the beginning of a brainstorm. It is operating at the front end of creativity.

And so if you can just allow everyone to be heard, have their ideas considered, they’re not going to care that you throw out the bulk of them later because they were seen, they were heard, the idea was there. And you’ll get to better ideas that way, especially ones that are co-created. You know, this myth we’ve got that there’s one single person who’s responsible for… You know, it’s the stuff I hate about Steve Jobs. And Steve Jobs was a genius of course, but he didn’t invent the iPhone alone. In fact, the iPhone was brought to him. I think the guy, he worked at Kodak. Is that the famous story? Yeah, the guy who invented the iPhone worked at Kodak. Kodak didn’t want to do anything with him. That was a mistake there. And so he shopped it around, and then through the collaboration with Jobs’ incredible sort of visual design mind and marketing mind, they were able to sort of birth this thing into the world. And that’s just how everything works. It’s not just one lone person.

Caitlin: It really is. It’s too bad that we––I don’t know about Eastern culture, I have not experienced very much of it personally––but I think in Western culture, we’re so attached to this idea of the lone genius.

Kelly: Yep, I think you’re right. I’ve been thinking about that a lot. And well, I’ve studied a bit of Eastern culture. Well, it’s sort of the Tao right? So in Eastern culture, everything is at least dualistic. And I think that is the difference because I think in Western culture, we end up looking for single solutions, we’re looking for the lone genius, things are right or wrong, they’re good or bad. And what much of Eastern culture has realised is that they’re all effects, they’re all things. My wife increasingly uses less “yes, and” and more “both, and” –– the idea being that, you know, if you really want to function at a high level, you have to understand that often in the moment both things are true. And your ability to sort of like, be agile in the moment with two opposite ideas is a sign of real intelligence and is probably a better way to get to what we end up being true.

Caitlin: But that’s terrifying for people to hold on to two truths, especially ones that seem oppositional in the moment and to sit with that and be able to go somewhere generative. How do you recommend people do that?

Kelly: They practice. Literally improvisation is a practice in that. You know, think about it. You are on stage alone. You have no script. You are allowing your partner to say words that then you have to truly listen to, and not prepare to respond, and just trust the fact that you will be able to respond in a coherent intelligent manner, that will then allow this thing to grow between you.

So again, I think the fear and shame reduction is a huge part of it, that frees up our sort of cognitive ability to be more agile. And then you’re just sort of practicing your attention, your breath, your wordsmithing, your physicality –– all these different things. You know, look, we’re all acting in the world as human beings. That is what we’re doing: we’re acting in the world. But we don’t have rehearsal. And we should. So if you can embrace a practice… Many people do this, it’s people who do Tai Chi, and people do Yoga, and people do improv are basically sort of saying, “OK. I need some practice in this area that will make me be more attuned in my day-to-day life.”

Caitlin: So what improvisational techniques in, say, in a meeting. There are like eight people in a room, they’re trying to come up with a new marketing campaign. What does it look like to use “yes, and” and other tools that you teach in a room in that way?

Kelly: OK, I love this one because people are terrible at meetings. So here’s the first thing: no meeting should be longer than 30 minutes, and really it should be no longer than 20 minutes. And you should designate the first five minutes of all “yes, and.”

Before that, you do not hold a meeting unless there’s a reason for the meeting, and everyone else understands the reason for the meeting. So before they even go into the meeting, they need to both: there’s got to be a reason for the meeting, and then they understand what the meeting is about, and generally what’s going to take place. Assuming the idea is to brainstorm a new marketing plan. The first five minutes are “yes, and:” you get the whiteboard out, and I want every idea––there’s no bad ideas––we’re going to write down every single thing here.

And then after that, what you have to make sure is that every person in that room is both not blocked. So, where are they at? Do I know where everyone is at? Is like, you know, does someone have an injury? Is someone have problems at home? Is someone happy? Has something really good happened to them? What’s the state of emergency consider level state, and so that everyone is very transparent with each other, like here’s where I’m at. Because that kind of shared truth––as we spoke about earlier––increases sort of group bond, but also just gives us an awareness that, “OK. John’s in a bad way. He’s got his mom’s sick. He is not going to be able to contribute in the way that he normally does. I need to pick up for that person.” And then they also have the freedom to step back a little bit.

So know where everyone’s at, and then allow the team to provide, you know, all the kinds of input that they need to. And then a leader really needs to listen to all of that, understand all of it, collect it, and then send everyone on the way. And be able to sort of sift through the ideas––this is where that leadership comes in––these guys give me a bunch of stuff now, I’m going to start to craft it, and before I bring them back together, I’m going to kind of get the gist of what I think I heard, and what I think is the best path to go. And that might be, here, these are the six ideas that really spoke to me. Let’s now get in the room and dig into these.

So there’s other stuff you can do, in terms of applying various improv theory, but I think this idea of controlled time and place, and acknowledgement of human suffering –– this is also something that’s ridiculous. Like, who said that we need to check our humanity at the door of the workplace? What do we have that separates us from the robots other than our humanity? That suffering and love and all of that is very powerful and totally at use.

Talking about a marketing meeting, that this is what you’re preying on –– the emotions of consumers. So you’ve got to bring your emotions. We have to understand. That doesn’t mean like we have crying rooms, it just means that you have ability to understand if someone’s happy or someone’s suffering, acknowledge it, it’s okay, you’re in a workplace. And so just generally speaking, I think we need to re-humanize our places of work.

Caitlin: I completely agree with you. Completely. What do you think is as at the center of people? What is the thing that you wish people took better care of in each other?

Kelly: That’s a really good question. I’m going to say radical inclusion. And what I mean by that is that, you know, we tend to not understand what inclusion really means, because what it means is empathizing with all people, and getting individuals out of this idea of you are X so that means you are Y. It means that, you know, we all contain failings and stupidity and we contain greatness, we’re complex. Some of us have really had bad cards dealt to us, sometimes that means we’ve been poor, we’ve been abused, sometimes that means we’ve been sheltered off in mansions, we’ve been badly educated, we’ve had weak mentors.

So, if we can sort of like approach our interactions with human beings from a place of radical inclusion, I am going to get to understand you and all of you before I judge you. And I’m going to do this person by person rather than the group that I think you’re in, or the group you say you’re in. I think that’s the only way to get out of the madness, the tribal madness that we find ourselves living in today. So I think that’s it.

Caitlin: Who taught you that? Or what taught you that?

Kelly: Everyone. And I say that actually with purpose. I think my experience at improvisation has allowed me to understand a really effective way to listen, and then also story-tell. And then, when I started hosting this podcast that I do called “Getting to Yes, And,” I get to talk to all these really cool thought leaders, academics, CEOs, Chief marketing officers, artists. And like I complete the learning loop: so I read the book, I have to then underline and sort of live the book as I’m doing my show notes. And then in talking to them, I’m sort of doing a knowledge transfer in the moment. And what I understand about how we learn is that’s the best way to learn is by getting the knowledge practicing the knowledge and then basically teaching the knowledge. And so I do this every week with someone different.

So I just spoke to a guy named Murray Nossel who’s a storytelling expert. And he was amazing, the first like 70 pages of his storytelling book are all about listening. I love that, you don’t even get to the other. He’s like, “If we can’t hear to listen first, we have no stories to tell.” And then he was such an elegant communicator. I can’t stop thinking about his stuff. But now I have to because I got to jump to the next book.

Caitlin: Yeah, I understand that feeling. What’s his book called?

Kelly: Powered by Storytelling by Murray Nossel.

Caitlin: That’s actually a lovely note to end on, because the way that I usually like to end on these talks is by asking the person I’m speaking with what they’ve read lately that they’ve enjoyed.

Kelly: Yeah, that’s a good one.

Caitlin: Thank you so much for your time. I really appreciate it. It was great to talk with you!

The Bookend

Ben: Welcome to The Bookend where we end… with books! I still like saying that.

Caitlin: I know, and I take so much delight in watching you enjoy it. I would never want to take it away from you.

Ben: So just to get right into this. The thing that really sticks with me about this interview. All of these celebrities that we talked about––Tina Fey, etc.

Caitlin: The Belushis…

Ben: The Belushi’s, Chris Farley, which I didn’t mention but I should, because I love him. Rest in peace. Belushis––also rest in peace. Dan Aykroyd. There’s a lot of people… Anyway, the one thing they had in common is it’s not that they were any funnier than any of the others, it’s that they were able to surrender themselves. I think it’s an amazing concept, like they could work successfully with other people––that might be the business application of this––but surrender yourself all of the time, get used to that, get used to giving yourself up, focusing on somebody else. I don’t know. I think that’s just an amazing insight.

Caitlin: Right, I totally agree. I think it also relates to the fact that improv is based on these agreements, and that the agreements between you and your partner, or your ensemble that one––I have your back, two––I will make you look your best, and three––I will rescind my need to be right. You have to be able to deny yourself the ego trips. And I guess “surrender” is the right word for that and agree that you’re there for the other person, and that is what allows that fear and shame part of your brain to click off, because you’re focusing on something outside of yourself, and focusing on your agreements and the task at hand, rather than how you’re feeling, and who you are, and who you think you’re supposed to be with someone in that moment.

Ben: So if people are into that, we should give them more books.

Caitlin: We definitely should!

Ben: Do you want to go first?

Caitlin: I do, I would love that. So my recommendation is actually a former Simplify guest, his name is Julian Treasure. He’s worked in sound branding for a while, he’s just basically an expert on listening and hearing really. He recently wrote this book called How To Be Heard, and I think it might have come out of a TED Talk that he did that has thousands upon, millions upon, numbers numbers views. People really really love this TED Talk. It gives these amazing practical pieces of advice on how to be heard and how to listen, which are really not as obvious as you would think, and it’s not something that we think about breaking down a lot. But in this book, Treasure talks about obstacles to effective communication. They can be hyperbole, so “You’re late all the time. You’re always late, Ben!”; people-pleasing which is, you know…

Ben: Can you think of an example for me?

Caitlin: I can’t! NO. And avoiding difficult difficult emotions, which is, I think, the thing we all do. So it has tips on how to deal with things like that. But also super simple stuff, like posture and eye contact. And he also gives listening exercises that you can, you know, do at home or with people that you’re talking to. So yeah, that’s called How To Be Heard, it’s by Julian Treasure, former Simplify guest from, I think it was Season 2. So go back and give that episode a listen too, we will have a link to it in the show notes. What are your picks?

Ben: I got two books. So when you were talking about surrender and enabling people to be their best, understanding who they are, Kelly Leonard mentioned Peter Drucker. And Peter Drucker is this like management consultant-writer-philosopher, who wrote like dozens of books about management. One of his most famous ones is called The Effective Executive. And it’s about how the effective leader “gets the right things done.” It’s got a little David Allen kind of vibe to it. And I think, David Allen likes Peter Drucker.

Caitlin: David Allen’s the Getting Things Done dude.

Ben: Exactly. The idea is the effective executive, which is a little fancy sounding––I would just say like a good leader, even a good colleague––knows how to focus on what’s important, helps people improve, focuses on people’s strengths. Right, don’t focus on the weaknesses, focus on the strengths. And basically in order to get the right things done, it means avoiding the wrong things, and avoiding unproductive things. So to me, that just sort of ties into this whole… I mean, I brought it up because Leonard mentioned it, and I can see this link between improv and a very hard business-management consulting book, which I think is really cool. And sort of related to that is my second recommendation, which is a book by Laszlo Bock who was the former senior Vice President of People Operations at Google. Basically like Head of People at Google. The book is called Work Rules. It’s like a play on words because it’s work rules! And also the rules work.

Caitlin: Yeah, work! Excellent!

Ben: Nice. And also Chicago.

Caitlin: This is a big hometown episode for you.

Ben: So Kelly Leonard mentions a Google study, where they found out that the key to working well in teams is actually psychological safety. It’s not efficiency productivity, Ivy league education, it’s actually psychological safety. And again this goes back to what you’re saying, surrender, not only know me, you know, my strengths, but also build an environment where I can surrender, where that’s safe, where I can be funny.

Caitlin: Right, where it’s safe for your fear and shame centers to shut down, and you can just be.

Ben: Yeah, so this book is really cool because it really shows from inside of Google, how they for example learn from their mistake of only hiring people from Ivy League schools, and to focusing on hiring people who have resiliency, and then it keeps going. Again, psychological safety––the way that you can build that––if you’re a leader or if you work in a team––is clear expectations, communication, communication, communication, authenticity and transparency. And transparency is a very difficult term, so like what Kelly Leonard says, essentially the answer to “Why are you asking me to do this?” And if you have all of that, you will have a great team.

Caitlin: Great!

Ben: Those are the books: Work Rules, How To Be Heard and The Effective Executive.

Caitlin: Effective executive… I can feel how much you enjoy saying that.

Ben: The effective executive, effective executive?

Caitlin: Yes, cool. All right. So then this episode is Simplify was produced by me, Caitlin Schiller, Ben Schuman-Stoler, Nat Darozhkina, Terence Mickey, and Ben Jackson who wanted us to tell you to stop replying to really long thoughtful emails with just the word “OK.”

Ben: You can find us on Apple podcast, Spotify, all the podcatchers you know and love. As always, if you like this episode, just share it and leave us a comment. We haven’t asked anyone to leave us comments, but we got comments. I like comments. I read comments.

Caitlin: Me too. We’d love to hear what you think of the season so far and you know, are you liking the guests? How about this format? Let us know what you think! We care and we use your feedback to make changes. So email us at [email protected], or you can talk to us on Twitter. I’m @CaitlinSchiller and Ben’s @bsto.

Ben: Yeah, and shout out to Juan Gabriel, who reached out to us via email a couple of weeks ago. That’s nice! Cool. So last thing, Simplify is made by the same people who make Blinkist, which––if you don’t know––is where Caitlin and I work. It’s a learning app that takes insights from the world’s best-selling non-fiction books and condenses them into these cute little capsules of knowledge that you can listen to or read in just 15 minutes.

Caitlin: And if you want to try it out, we made another voucher code for this episode. That means that you can go to type in the voucher code: “yesand” and you get 14 days free.

Ben: All right, then that’s it. Checking out!

Caitlin: Till next time! Checking out.

Ben: Is this the last episode of the Season?

Caitlin: Maybe, maybe not.

Ben: Episode 6?

Caitlin: Episode 6.

Ben: We did it. We did it again! Another season. They said we wouldn’t do it! Nobody said that…

Caitlin: No, everybody said we would and we had to.

Ben: Do you know, if there’s going to be a bonus ep?

Caitlin: Yep, I think that there might be. So stay tuned, in a couple of weeks you will be seeing one more episode from us.

Ben: Alright, Season 4 in the bag!

Caitlin: Yes, nice! Silent high five.

Ben: Alright, checking out!

Caitlin: All right. Checking out!

Ben: See ya!

Caitlin: Bye!

Read the show notes from this episode here!

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