Description

Episode Summary

When the world continues to throw new challenges your way, improv might be the most important life skill you’ve never learned.  Collaboration, reading a room, dealing with failure, Kelly Leonard of legendary The Second City theater details how improvisation can benefit your life beyond creating a great sketch comedy.  Kelly shares what it was like seeing John Belushi and Chris Farley on stage, working with Tina Fey and Stephen Colbert, what actor really surprised him, and more from behind the comedy curtain, in this episode of The Sydcast.

Syd Finkelstein

Syd Finkelstein is the Steven Roth Professor of Management at the Tuck School of Business at Dartmouth College.  He holds a Master’s degree from the London School of Economics and a Ph.D. from Columbia University. Professor Finkelstein has published 25 books and 90 articles, including the bestsellers Why Smart Executives Fail and Superbosses: How Exceptional Leaders Master the Flow of Talent, whichLinkedIn Chairman Reid Hoffman calls the “leadership guide for the Networked Age.”  He is also a Fellow of the Academy of Management, a consultant and speaker to leading companies around the world, and a top 25 on the Global Thinkers 50 list of top management gurus.  Professor Finkelstein’s research and consulting work often relies on in-depth and personal interviews with hundreds of people, an experience that led him to create and host his own podcast, The Sydcast, to uncover and share the stories of all sorts of fascinating people in business, sports, entertainment, politics, academia, and everyday life. 

Kelly Leonard

Kelly Leonard began his Second City career in 1988, eventually becoming a producer of Second City in 1992 and Executive Vice President through 2015.  He has produced hundreds of original revues with talent such as Stephen Colbert, Tina Fey, Keegan Michael Key, Seth Meyers, and Amy Poehler.  His book, Yes, And: How Improvisation Reverses "No, But" Thinking and Improves Creativity and Collaboration--Lessons from The Second City, received rave reviews in Vanity Fair and the Washington Post. He co-leads a new partnership with Booth School at the University of Chicago that studies behavioral science through the lens of improvisation. He is a popular speaker, appearing at Aspen Ideas Festival, Chicago Ideas Week, and TEDxBroadway.  Kelly also hosts the Second City Works/WGN Podcast Getting to Yes, And.

Insights from this episode:

• Details on how Kelly went from a dishwasher to a producer at Second City, his life outside of the theater, and why improv has become life.
• Reasons why charisma is a blessing and a curse and whether it is something you are born with or something you can develop.
• Benefits of using improv skills to build a better business, be a better parent, and become comfortable being uncomfortable.
• Strategies for dealing with loss and how to console someone who has experienced loss.
• Details on working with some of the biggest names in comedy, the relationship between Second City and Saturday Night Live, and how COVID has changed the creative process at Second City versus other comedy shows.

Quotes from the show:

• On charisma: “It’s not a superpower unless it can be used for evil.” – Kelly Leonard
• “I find it an artificial conceit that somehow business operates differently than the rest of the world and life.” – Kelly Leonard
• “Anyone can learn information but the ability to take that information and apply it successfully in collaboration with others is the real thing you need.” – Kelly Leonard
• “The only way innovation happens is when you experiment over and over, which is a majority of failures, on your way to eventual success.” – Kelly Leonard
• On failure: “If you don’t admit it, you don’t acknowledge it, there’s not much opportunity there to learn from it.” – Syd Finkelstein
• “You can not be in a creative mindset and be analyzing and judging yourself at the same time.  You have to suspend that entirely.”  – Kelly Leonard
• “That is the great mark of an improviser, is their ability to be fearless and sometimes even follow their fear because making yourself uncomfortable allows you to learn new things about yourself.” – Kelly Leonard
• Creativity is a discipline, it might sound strange, but it is like any other amazing skill and you’ve got to practice it, you’ve got to do it.” – Syd Finkelstein
• On how he dealt with the loss of his daughter, Nora: “We have a saying, play the scene you’re in and not the scene you want to be in, and that’s what we did, we played the scene we were in.” – Kelly Leonard
• On operating during COVID: “We’re doing work in ways that we’ve never done before and we should be proud of that, but we can’t stop.” – Kelly Leonard

Stay Connected:

Syd Finkelstein

Website: http://thesydcast.com

LinkedIn: Sydney Finkelstein

Twitter: @sydfinkelstein

Facebook: The Sydcast

Instagram: The Sydcast

Kelly Leonard 

Website: www.secondcity.com/people/other/kelly-leonard

Twitter: @KLsecondcity 

Book: Yes, And: How Improvisation Reverses "No, But" Thinking and Improves Creativity and Collaboration--Lessons from The Second City

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This episode was produced and managed by  Podcast Laundry (www.podcastlaundry.com)