In a Nutshell: In 2020, business leaders had to be fast on their feet in order to adapt to the daily challenges of the pandemic. But developing your improvisational skills can also help you make meaningful human connections that will improve your management performance and strengthen your personal relationships.

Guest: Kelly Leonard, the Executive Director of Insights and Applied Improvisation for The Second City in Chicago. During his more than 30 years with the company, he has produced hundreds of original shows with talent such as Stephen Colbert, Tina Fey, Keegan Michael Key, Seth Myers, and Amy Poehler.


My Key Takeaways:

  1. Ensembles are stronger than teams. A group that’s focused on supporting every member and strengthening each other’s weaknesses is going to achieve more than a random collection of good talent.
  2. “Yes … And …” The golden rule of improv can turn down negativity and foster a more inclusive creative environment.
  3. Find unorthodox connections. Sometimes the shortest distance between point A and point B is boring. Real discovery and innovation happens when your team feels empowered to carve a new route.

Also Learn:

  1. How The Second City continues to thrive even with its regular turnover of superstar talent.
  2. What kinds of connections Kelly and his colleagues have discovered between improvisation and behavioral science.
  3. Why Kelly believes that improv is “yoga for your social skills.”

Complementary blog post: Michael Port, a New York Times best-selling author, professional speaker, and former TV and movie actor, talked to me about the roles we all play in our businesses and our lives. Listen/read here.

Resources Featured In This Episode

Kelly Leonard