How Improv Skills Can Transform Business Relationships with Second City’s Leader Kelly Leonard

What if improvisation wasn’t just for comedy, but a game-changer for business, relationships, and even personal growth?

In this episode, I sit down with Kelly Leonard, the creative force behind Second City's groundbreaking use of improv training in the corporate world. From recruiting comedy legends like Tina Fey and Steve Carell to co-authoring the acclaimed book Yes, And, Kelly shares stories, insights, and research-backed techniques that redefine how we approach collaboration, listening, and adaptability. You'll learn how to build trust, navigate ambiguity, and create powerful ensembles in business and life.

Kelly also delves into the science behind improv. Whether you're prepping for a high-stakes pitch, navigating personal challenges, or just looking to sharpen your creative edge, this episode will leave you inspired and equipped.

 

Topics We Cover in This Episode: 

 

• The “Yes, And” philosophy and how it fosters creativity and collaboration

• A surprising FBI training exercise to build agility under pressure

• How to turn disagreement into a productive conversation with one simple phrase

• Stories of famous improvisers and the magic of ensemble thinking

• Why listening deeply is the ultimate superpower in high-stakes situations

• How improv can help heal anxiety and build resilience

• The unexpected ways improv transforms both individuals and organizations

 

If you enjoyed this conversation with Kelly Leonard, dive deeper into his world! Check out my interview on Kelly’s podcast, Getting to Yes, And. Don’t miss his acclaimed book, Yes, And, a must-read for anyone looking to elevate their collaboration and creativity.

Learn more about The Second City here, and tune into Kelly’s podcast here. You can also connect with Kelly directly on LinkedIn or follow his updates on X.

 

Resources Mentioned:

Listen to the Give to Grow episode on Kelly’s Podcast: ​​https://www.secondcity.com/network/mo-bunnell-give-to-grow 

Check out Kelly’s book, Yes, And: https://a.co/d/6f6lDYT

The Seconde City: https://www.secondcity.com

Subscribe to Kelly’s podcast: https://www.secondcity.com/network/category/getting-to-yes,-and-podcast

Connect with Kelly on Linkedin: https://www.linkedin.com/in/kelly-leonard-b8495047/

Connect with Kelly on X: https://www.twitter.com/KLsecondcity 

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