How Improv Comedy Can Seriously Help Your Business

After graduating cum laude from Lake Forest College and winning a Phi Beta Kappa Thesis Award for outstanding scholarship, Kelly Leonard went home and announced that he wanted to pursue a career in theater. His father was thrilled! 

“My father was probably the only one in America who was like, ‘thank God,’ he doesn’t want to be a banker or a journalist or a lawyer,” says Leonard. “If I said I wanted to be a doctor, he’d have been so disappointed.” His father, Roy, was a longtime Chicago radio personality who appreciated the performing arts and regularly talked theater and film during his 31 years on air. 

While Leonard imagined life as a playwright, he instead found success at Chicago’s famed improv comedy theater Second City, where he is vice president, creative strategy, innovation and business development. Famous Second City alumni include Bill Murray, Chris Farley, and Julia Louis-Dreyfus; Leonard’s eye for talent led him to personally hire Tina Fey, Amy Poehler, and Jason Sudeikis, among other comedy legends. 

But, before that, like so many theater kids, Leonard just wanted a big break, and luckily his father has some connections. One of those was Second City co-founder Bernie Sahlins who was starting a new venue when Leonard reached out to him. Sahlins promised Leonard a job as a production assistant once his new theater opened. In the meantime, he helped Leonard land a job at Second City.

“I show up there on a Friday night in October 1988 and I was supposed to be at the front bar—but I was escorted back to the kitchen and started as a dishwasher,” Leonard says. “The other guy who got hired that week to wash dishes was Jon Favreau (now a film director known for “Iron Man” and “Elf,” among others). We both had mullets.” 

Sahlin’s new theater opened, bombed, and Leonard went back to Second City working in the box office. Then, in 1992 at the age of 24, he got his really big break, becoming a show producer. His first cast included Stephen Colbert, Steve Carell, and Amy Sedaris. He produced hundreds of original shows until 2015 when he co-wrote the best-selling book Yes, And, which focuses on how improvisational techniques can be used to address business issues. The success of the book led Leonard to shift his focus to Second City Works, the theater’s training and coaching division. 

“The first part of my career was improv on stage, and the second part was improv off stage,” Leonard says.

The “Yes, And” Concept

“What we know from behavioral science is that people's default position is to say “no” or do nothing,” says Leonard, who co-leads a partnership with the Booth School at the University of Chicago where behavioral science is studied through the lens of improvisation.

“‘No’ is a very protective tool for us, and what we know about the human brain is that we crave security, we crave predictability, but we do not live in a predictable environment, and we never have,” says Leonard. “So, people's inclination to make themselves safe and say “no” is something we need to get them to move past. Saying ‘no’ means you don’t make new discoveries; you invent nothing new. It’s inaction.”

“Yes, and,” is the opposite. “The concept is making something out of nothing. It’s front-end creativity, a place for exploring that leads to a bunch of ideas and gets you to something innovative” says Leonard. “In improvisation, any idea that someone gives you on stage, you affirm to them, and you explore, and you heighten by adding to it. So, yes, whatever someone said to you is correct, no matter what, and if that means you end up talking about monkeys on Mars, then it’s monkeys on Mars.” 

The ways in which the “yes, and” concept applies to the business world are many. The practice allows you to be influenced by other people’s information and ideas in a positive way and, in turn, influence others. And it supports the idea of there being no bad ideas. “Bad ideas are good—in fact, I would like your bad ideas because one person's bad idea is another person's portal to something innovative,” says Leonard. The practice is not easy and to be successful you need to avoid judgement and self-doubt because that is how you quickly default to “no.”

“This is why Tina Fey and Stephen Colbert and Amy Poehler have had such successful careers because they use this practice not just for their material but as a life skills,” says Leonard. 

Improv as a Superpower: Comedy Techniques in the Business World

When someone asks Leonard how improv comedy techniques correlate to the business world, he responds by asking them two questions: 

1. Does your business success rely on human beings interacting well with other human beings? (Their answer is yes)
2. Are you always working with a script? (Their answer is no)

“What I say about improvisation is that it’s a practice in incredible communication skills. It teaches people how to create without a script, and it involves deep listening,” says Kelly. “It also involves resilience and learning the things we need to know in order to work well together because work is not a solo act, life is not a solo act.”  

Those are important skills in the business world where you frequently encounter unexpected challenges and need to pivot (essentially another word for improvising). You need to explore creative ways to overcome challenges, know how to help people and be helped, and forge ahead without a script (the “yes, and” concept). That’s the superpower.

Second City had a training center almost from its inception—well before the publication of Yes, And—but it wasn’t geared toward business training and coaching. However, a lot of people who were signing up were not looking for stardom. “They were coming here not to get on the Second City stage and not to get to get on “Saturday Night Live,” but because they thought the techniques might help them in their relationships or their work,” says Leonard. “We recognized that there could be a business here.”

At first, they produced training videos—some starring young Stephen Colbert and Steve Carell—but over the years the program transitioned into workshops, and that’s the program they’ll bring to the Pinnacle Experience conference.

“We’ve had close to 40 years of recognizing how improv techniques can impact people in the business world, help manage change and growth, and just make people’s working days better,” says Leonard.

His workshops will be interactive, instructive, and help you connect with ideas you’ll want to bring back to your workplace. “You don't know until you open up your world to these ideas what you're going to get back,” says Leonard.

And he promises a great time. “I tell stories. I've worked with a lot of really famous people in early parts of their careers, and I like to tell stories about them,” Leonard says. “The best learning is fun, so we're going to play a little bit.”