Episode 10 –
The Art of Improvisation in Business with Kelly Leonard

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RESOURCES   ❯   The Marketing Rapport Podcast

Episode Summary

In this episode of The Marketing Rapport, host Tim Finnigan speaks with Kelly Leonard, Vice President of Creative Strategy, Innovation, and Business Development at Second City. Kelly shares 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.

Kelly delves into how improv can be used as a tool to navigate through high-pressure situations and adapt to unforeseen challenges. Drawing on real-life stories and experiences, he highlights how the principles of “yes, and” can foster a collaborative and supportive environment, allowing individuals to grow and thrive in their professional lives.

As a parent and a seasoned professional, Kelly provides a unique perspective on the difficulties faced by the younger generation entering the workforce today. His empathy, combined with his expertise in improvisation, offers valuable insights for aspiring and established leaders looking to effectively navigate and excel in the complex landscape of today’s workplace.

Guest-at-a-Glance

Key Insights

• The Power of “Yes, And” in Business Kelly Leonard discusses the importance of the “Yes, And” philosophy in business, highlighting how it can foster collaboration, creativity, and innovation. He shares examples of organizations that have successfully applied this approach, including Google, NASA, and The White House. By embracing “Yes, And,” teams can listen to one another, support each other’s ideas, and build on them, leading to better decision-making, enhanced problem-solving, and more productive working relationships.
• Talent Development and Retention through Improvisation Kelly emphasizes the role 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. He talks about how improvisational techniques can help nurture employees’ potential, maximize productivity, and foster a deeper connection to the company. By understanding their dreams and aspirations, and giving them the space to achieve them, organizations can create an environment where employees thrive and form lifelong connections.
• The Importance of Vulnerability and Struggle in Leadership Using examples of great leaders like Churchill, FDR, and Kennedy, Kelly explains how vulnerability and struggle can help leaders connect with their teams and persuade others more effectively. He suggests that by sharing their vulnerabilities and struggles, leaders can humanize themselves and inspire trust among their team members. This approach aligns with the improvisational mindset, encouraging openness and collaboration, and enabling organizations to better navigate the complex challenges they face.

Episode Highlights

The Influence of Improvisation on Creativity

In the podcast, Kelly Leonard shares how improvisation can unleash creativity and innovation within an organization. He discusses how embracing uncertainty and working together in the moment can lead to new ideas and solutions. Kelly explains how the principles of improv can help teams become more adaptive and responsive to change, thus increasing their ability to innovate.

“Improv is the ultimate agile system. It is an approach to human interaction based on change and flexibility, the ability to work together with other people in the moment to create something out of nothing.”

The Loneliness Epidemic and Mental Health Crisis

Kelly addresses the growing concerns around the loneliness epidemic and the mental health crisis, particularly among young people. He suggests that the anxiety and fear they experience may be a rational response to the uncertain world they face, such as school shootings and the burden of student loans.

“Is there a chance that what people are picking up on is an absolutely rational response to what is in front of them? Which is a world that looks on fire, which is, uh, young people going to schools not knowing if they’re gonna be shot or not, which is people having to pay off exorbitant student loans or thinking they’re never gonna pay those off.”

Real-Life Stories and Business Lessons in Kelly’s Book

Tim Finnigan commends Kelly Leonard’s book for its combination of engaging storytelling and practical business lessons. The book covers topics like problem-solving, brainstorming, communication, and leadership skills, all of which are essential for thriving in today’s business environment.

“Another plug about your book is that you tell a great story, but it’s rooted in truth as far as real-life stories and business stories and people want to understand on how to solve problems and how to brainstorm and ideate better, how to communicate with your team better and leadership skills.”

Improv as a Tool for Personal Growth and Popularity

Kelly shares a personal story about his son, who discovered the power of improv in helping him overcome bullying and find acceptance. By embracing the principles of improv, his son learned that being nice and funny could lead to popularity, showing how improvisation can be a valuable tool for personal growth and social success.

“In improv, if you’re nice and you’re funny, you’re popular. I tell this story almost every speech I give, I open with it. And I do that for a couple different reasons. One is that it’s never left me. It’s a thing I still think about today when I think about why do I get up in the morning and come to work? And that’s the reason.”

Top Quotes

Kelly Leonard [00:04:56]: “Improv is the ultimate agile system. It is an approach to human interaction that is based on change and flexibility, the ability to work together with other people in the moment to create something out of nothing.”

Tim Finnigan [00:31:01]: “Another plug about your book is that you tell a great story, but it’s rooted in truth as far as real-life stories and business stories and people want to understand on how to solve problems and how to brainstorm and ideate better, how to communicate with your team better and leadership skills.”

Kelly Leonard [00:32:38]: “In improv, if you’re nice and you’re funny, you’re popular. I tell this story almost every speech I give, I open with it. And I do that for a couple different reasons. One is that it’s never left me.”

Kelly Leonard [00:29:09]: “Is there a chance that what people are picking up on is an absolutely rational response to what is in front of them? Which is a world that looks on fire, which is, uh, young people going to schools not knowing if they’re gonna be shot or not, which is people having to pay off exorbitant student loans or thinking they’re never gonna pay those off.”

Tim Finnigan [00:10:45]: “You said something in your book that really struck me, ‘We are not the most important person in the room, our scene partner is.’ That is so powerful and I think it really resonates with a lot of people.”