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Simplify Collaboration: Kelly Leonard On How To Grow Teams With Improv

In this episode of Simplify, Caitlin talks to The Second City executive Kelly Leonard about how improv-based skills can be applied to the business world.
by Natallia Darozhkina | Sep 27 2018

Effective collaboration, innovative thinking, and constructive problem-solving can be major struggles for many teams, regardless of industry. But for those who really want to fix these issues, it’s time to look beyond how other companies work and turn to improv comedy ensembles for inspiration. After all, they’ve literally taken teamwork and turned it into an artform.

Reflecting on years of experience with Chicago’s famous Second City improv troupe — where comedians like Tina Fey, Stephen Colbert, and Dan Aykroyd cut their teeth — Kelly Leonard explains how improv techniques can benefit the business world. From fostering better communication to generating better ideas, improv can help to build teams capable of rising to any challenge.

Leonard gives useful advice and practical exercises on how to get the most out of a meeting, what kind of environment should be created at a workplace, and how to build trustworthy and respectful relationships inside the team to improve collaboration and get better ideas.

“…Team implies competition, and ensemble is a mindset.”
Kelly Leonard

Listen to this episode to learn business tips that are used on stage by some of the world’s best comedians, and discover the key to truly outstanding teamwork.

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Who’s Kelly Leonard

Kelly Leonard

Kelly Leonard is the Executive Director of Insights and Applied Improvisation for The Second City. From 1992 to 2015, he was the Executive Vice President of Second City and The President of Second City Theatricals, hiring talent, directing shows and producing all the live theatrical work with such notable performers as Stephen Colbert, Tina Fey, Steve Carell, Amy Poehler, Jason Sudeikis, etc. In 2015, Kelly co-wrote a book with Tom Yorton called Yes, And on how to apply improv-based pedagogy to businesses and individuals to make their working lives better. He lives in Chicago with his wife Anne Libera and their children Nick and Nora.

Kelly Leonard’s recommended reads

1. Powered by Storytelling: Excavate, Craft, and Present Stories to Transform Business Communication by Murray Nossel

In this book, executive coach, motivational speaker, and psychologist Dr. Murray Nossel explores how storytelling can enhance business communication, transform workplaces and help your business thrive.

Extra Credit Reading

How to be Heard identifies proven ways to become a powerful speaker, the kind that commands people’s attention and keeps them hanging on your every word. Author Julian Treasure also examines the steps people can take to improve their listening skills, allowing them to better understand what’s being said and making the listener feel that they’re being heard. These tips can help improve both communication skills and our most important relationships.

Work Rules! takes us through the inner workings of Google, one of the most powerful and successful companies in the world. Bock tells us precisely how Google pulls off this feat while consistently being ranked as the best employer in the world.

In The Effective Executive, author Peter Drucker offers a step-by-step guide to becoming a more productive and effective executive. By mastering a few procedures and principles, you can develop your own capacities as a leader and also support your employees’ strengths, with the goal of improving results across your organization.

What’s Simplify?

Simplify is a podcast for anybody who’s taken a close look at their habits, their happiness, their relationships, or their health and thought “There’s got to be a better way to do this.” We talk to bestselling writers, productivity wizards, sex geniuses, and happiness experts to find it for you.

Simplify is made with love by Blinkist. Click here to try Blinkist free for 14 days with the voucher code: yesand

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Talk to us!

We want to hear from you! Drop a line to us at [email protected] about whatever tickles your fancy.

If you want to say hi to Caitlin and Ben in the meantime, you can find them on Twitter: @CaitlinSchiller and @bsto.

Who made this?

Your hosts are Caitlin Schiller and Ben Schuman-Stoler.

Research and production assistance by Nat Darozhkina and Terence Mickey, sound and editing by Ben Jackson and Ody Constantinou.

Thanks to Nico Guiang for our awesome intro and outro music. Listen more on Soundcloud or check him out on Facebook.

Got links?

Second City website:
Julian Treasure on Simplify Season 2:

Read the transcript here!

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