Kelly Leonard’s career began with a decision that surprised his father. After graduating from Lake Forest College, Leonard chose theater over banking or law. “My father was probably the only one in America who was like, ‘thank God,’” he recalls. His father, Roy, a Chicago radio personality, supported his son’s choice. Leonard’s path led him to Chicago’s Second City Theater, where he later became vice president of creative strategy, innovation, and business development. Famous alumni include Bill Murray and Tina Fey, whom Leonard personally hired.
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Leonard’s early days at Second City were humble. His work in improv comedy extended beyond the stage, culminating in the 2015 book Yes, And, which explores how improv techniques apply to business.
At the heart of Leonard’s philosophy is the “yes, and” concept. “People’s default is to say ‘no’ or do nothing,” he explains. “No is a protective tool, but it stifles creativity.” Improv demands adopting ideas, even absurd ones. “If someone suggests monkeys on Mars, you go with it.” This approach supports collaboration and innovation, rejecting the idea of “bad” ideas. “One person’s bad idea is another’s portal to something new,” Leonard says.
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The “yes, and” principle, he argues, helps teams avoid self-doubt and judgment. “Tina Fey and Stephen Colbert succeeded because they used this as a life skill,” he notes. Improv teaches listening, resilience, and adaptability—skills critical in business, where changing direction is often necessary.
Second City’s training programs, which predate Yes, And, initially focused on personal growth rather than corporate training. Many attendees sought techniques to improve relationships or work performance, not stardom. Over time, workshops emerged, blending improv with business strategy. “We’ve seen how these techniques manage change and make workdays better,” Leonard says.
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At the Pinnacle Experience conference, Leonard’s workshops aim to be interactive and fun. “The best learning is fun,” he insists. He shares stories from his time with early-career stars, emphasizing that creativity thrives when people feel safe to explore. “You don’t know what you’ll get back until you open up to these ideas,” he adds. For Leonard, improv isn’t just a comedy tool—it’s a superpower for business and life.
