Kelly Leonard, The Second City: Improv and Business Share the Same Stage

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The Second City is arguably the most renowned and important improv institution in the world. Tina Fey, Amy Poehler, and Stephen Colbert all honed their craft in Chicago on The Second City stage. Kelly Leonard hired each of them, along with many other budding stars throughout the 1990s and 2000s, when he oversaw Second City’s creative expansion and development. In 2015 he co-authored the book, Yes, And. Today, Leonard is the executive director of applied improvisation at Second City Works, the business arm of The Second City, and he’s the host of the Getting to Yes, And podcast. He joins us to talk about how applying improv to business teaches us to listen and focus effectively, collaborate with others, and be ready for change. Because business life isn’t any different from human life. We just need to listen to each other more, embrace our failures, and keep improvising.

Listen to this episode to learn:

  • Why improv is essentially “human being practice” that teaches us how to make something out of nothing — and that’s what we do in business, too
  • How rehearsals and synchronicity create “peak performers” in the arts…and in business
  • Why organizations (and the humans within them) have a listening problem, and what we can do to fix it
  • How isolation and a “conspiracy of silence” around suffering ultimately hurt us at work
  • Why it’s better to incorporate many failures into your success narrative rather than try to beat failure out of you
  • The one improv technique you can start using today to create a better connection with your coworkers

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