When Second City executive vice president Kelly Leonard gave Tina Fey creative space, she made a two-woman show alongside Rachel Dratch called "Dratch and Fey," which ultimately convinced Lorne Michaels to hire the duo as Saturday Night Live cast members. When Leonard gave Horatio Sanz creative space, he threw a prop bag out a hotel window, shattering the windshield of his traveling comedy troupe’s van.
Strong leaders understand that each member of a creative team needs to be managed differently. Such is true whether your team is comprised of marketers, salespeople, designers, developers—or young comedians bound for stardom.
"You need to be creative to lead creatives," says Leonard, now a creative adviser for Second City and coauthor of Yes, and: How Improvisation Reverses ‘No, but’ Thinking and Improves Creativity and Collaboration. "That doesn't mean that I have to be the artist; what it does mean is that I have to bring artistry to my leadership. When you do that, you can really help unlock a lot of possibilities for these people to do their best work for you."
Over the course of more than 20 years serving as Second City’s executive vice president and director, Leonard recruited, nurtured, and managed some of the most talented performers of a generation. Each experience, he explains, taught him how to be a better leader and how to better manage the creative talent passing through Second City’s doors. Here are some of the key lessons he learned from Second City alumni:
It’s difficult for leaders to admit that they’re not the smartest person in the room, but Tina Fey forced Leonard to come to that conclusion quickly after they begin to work together. Though Leonard officially called the shots, he learned that highly creative individuals work best when leadership steps out of the way.
"When you have someone who is that skilled and is that good at what they do, you need to make sure they don't have barriers in their way," says Leonard. "Luckily I was smart enough at the time to figure out that she probably knew better than me 90% of the time, so the good-boss move on my part was just to stay out of her way. That became a very successful formula when we worked together."
While the Tina Feys of the world work best when given space to create, those like the hyperactive Horatio Sanz need clearly defined boundaries.
"He never stuck to the script, he frequently behaved badly, and I'm still finding out stories now," says Leonard, adding that Sanz only revealed the shattered windshield story recently.
"Horatio was a challenge for me, because it was, 'How do I create appropriate boundaries to let him have some rope but not strangle himself?" says Leonard. "He was the opposite of Tina. I couldn't give Horatio blue sky, what I had to do was say, 'I need you, for the sake of the show's integrity, to stay close to the script,' and that would work for about two weeks."
Working with Sanz taught Leonard to manage each member of a creative team differently. "If you try to keep the rules the same for everyone, than you're going to get middle-of-the-road creativity," he says.
Amy Poehler’s stint at Second City was shorter than most, or at least shorter than Leonard would have wanted. Though he quickly realized Poehler was bound for greatness, one of his biggest regrets is not using her talent to the fullest while he had the chance.
Poehler joined Second City in 1993, and soon began to work with the company’s touring group. Less than three years later, she and the Upright Citizens Brigade moved to New York City, before Leonard had given her the chance to perform on Second City’s main stages.
"Probably the biggest regret I have is not finding a way to move her up sooner," he says. "The cautionary tale there with someone like Amy is when you see someone who is that good, you have to find places for them, because if you don't, they're going to be gone."
Though some like Amy Poehler had an unusually short stint with Second City, others, like Steve Carell, stuck around for an unusual length of time. Leonard explains that in most cases, if he’s done his job properly, performers pass through Second City after three or four years on their way to bigger things. Such was not the case for Steve Carell, who remained at the theatre for nine years.
"He took his time, did good work, kept his head down, and didn't fret about the future; he just concentrated on being good at his job," says Leonard. "Steve Carell taught me that talent wins out. If you're good, just keep at it, keep doing your stuff; it's going to pay off."
Leonard likens Poehler’s earliest performances to fireworks, adding that unlike Carell, those around her knew right away she was destined for fame.
"Arguably, those two are equally famous now," he says. "Don't assume that because someone's been in their position for a long period of time, that they don't have the ability to grow out of that. Sometimes it just takes a little bit longer for creative people; it's not all fireworks."
Though Keegan-Michael Key is famous for showcasing racially charged humour alongside Jordan Peele in their sketch comedy show Key & Peele, Leonard says Key brought a level of diversity to Second City he wasn’t entirely prepared for, and it had nothing to do with skin color.
"Keegan was the first born-again Christian I ever worked with at Second City," he says, adding that organized religion was a common target of the theatre’s satire.
Leonard recalls one sketch where Key was asked to play Jesus during the last supper. "They're giving him a going-away present, and it's a classic picture of white Jesus, and he's getting angry, like, 'That doesn't look like me at all!" he says. "He taught us something that we already knew, which is the more diverse voices that you have inside a creative institution, the more powerful you're going to be."
As Leonard would learn shortly after recruiting him, Stephen Colbert is a man of strong principals. Leonard recalls one particular sketch based around a children’s spelling bee, where a Jewish actor was asked to spell the word "compass."
"She says, ‘Can you use that in a sentence please?’ and Stephen says, ‘Sure. Your people killed Jesus. Compass," says Leonard. A week before the show was set to open, Colbert approached Leonard in his office asking him to pull the scene.
"I recall this as being a four-hour—and I’m sure it wasn't—but a lengthy conversation about the role of a satirist, about how you can take responsibility as a performer so that people understand your intent," he says.
After a lengthy debate, Colbert agreed to keep the sketch in the show, but Leonard believes to this day that had he dismissed Colbert’s concerns, he would have quit.
"What you can't do is play it my way or the highway; that's terrible leadership, especially for creative individuals," he says. "You have to be willing to have the difficult conversations, and you have to be willing to lose."