Report: The Future of Insurance


The Art of Improvisation in Business with Kelly Leonard

What does improv have to do with successful business practices? A lot, actually.

Second City is the oldest ongoing improvisational comedy theater troupe to be continually based in Chicago. It has consistently been a launchpad for many legendary comedians, award-winning actors, directors, and others in show business. Second City also serves as an enterprise that helps businesses improve their performance through the principles of improv.

Kelly Leonard, Vice President of Creative Strategy, Innovation, and Business Development at Second City, sat down with The Marketing Rapport host Tim Finnigan and shared his thoughts on the importance of improvisation skills in the ever-changing world of work and the impact of these skills on leadership, teamwork, and personal development.

As a parent and seasoned professional, Kelly provides a unique perspective on the difficulties faced by the younger generation entering the workforce today. With his empathy, expertise in improvisation, and passion for behavioral science, he offers valuable insights for aspiring and established leaders of today’s workplace.

Read on for highlights from the episode or listen now on Spotify, Apple Podcasts, and our website.

The power of “Yes, And”

Kelly discussed the importance of improv’s “Yes, And” philosophy in business, as it can foster collaboration, creativity, and innovation. He shared examples of organizations that have successfully applied this approach, including Google, NASA, and The White House.

“The idea is that if people are prone to say no, you teach them a practice in which they don’t just say ‘yes,’” Kelly said. “They say, ‘Yes, and!’ They affirm and contribute in order to explore and heighten.”

By embracing “Yes, And,” Kelly argued that teams can listen to one another, support each other’s ideas, and build on these ideas, which leads to better decision-making, enhanced problem-solving, and more productive working relationships.

Improvisation as an Organization’s Creativity Engine

Kelly emphasized the role that improvisation can play in talent development and retention, citing his experience at Second City, where he worked with talents like Tina Fey and Stephen Colbert.

One reason that improv can be so fruitful for employees is that business may be thought of as one great act of improvisation. “Improvisation is elemental to human beings coming together in groups and making something out of nothing,” Kelly said. “People in the startup world totally get this as soon as I say it. The importance of improvising is not just true in startup culture, though. It’s true more broadly.”

Creativity for the Future of Business

Tim praised Kelly’s book, Yes, And: How Improvisation Reverses “No, But” Thinking and Improves Creativity and Collaboration—Lessons from The Second City, for its combination of engaging storytelling and practical business lessons.

“You tell a great story,” Tim said on the podcast, “but it’s rooted in the truth of real-life stories and business stories. People want to understand how to solve problems and how to brainstorm and ideate better, how to communicate with their team better, and how to become more effective leaders.”

Kelly’s thoughts about the future of business are not just grounded in experiences from his own life, but also in the stories of historical leaders, such as Churchill, FDR, and JFK. He explained that when leaders allow themselves to be vulnerable, they can better connect with their teams and persuade others more effectively. This humanization goes well with the improvisational mindset, since both encourage openness and collaboration.

Empowering Yourself During Stressful Times

Amid the rapid technological changes and information overload in our society, Kelly added that “There’s a sea change in companies, where they are recognizing that they have to pay attention and are using terms like ‘mental health’…is there a chance that what people are picking up on [when talking about the loneliness epidemic] is actually a rational response to what is in front of them? It’s a world that looks on fire…a world where people wonder what it means to have purpose at work.”

One way to mitigate this rational anxiety is through the power of improv to gain control over your own life. Kelly shared a personal story about his son, who used improv to help him overcome bullying and find acceptance. By embracing the principles of improv, his son learned that being nice and funny could, in fact, result in popularity, growth, and success.

For Kelly, leadership, business, and success all come down to helping your people embrace their creativity to find happiness. “When you can understand what your people want, understand what they’re dreaming, you can give them space to accomplish that dream. Then you don’t just have a happy employee—you have a lifelong friend.”

Listen to the full episode now on Spotify, Apple Podcasts, and our website.

Find Kelly Leonard on LinkedIn.

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