Mastering the “yes, and” mentality with Kelly Leonard, VP of Creative Strategy @ Second City, Pt. 2

Question Everything

On this episode of the QE podcast, listener-favorite Kelly Leonard is taking a well-earned victory lap. After dropping countless stories and lessons from his time at The Second City, he’s ready to once again face our gameboard and humor us with his industry wisdom for a second installment. His first episode is a must-listen, so if you missed it, be sure to check it out on Spotify and Apple Podcasts.

If you’re new to Kelly, here’s a reintroduction: Kelly Leonard is the VP of Creative Strategy, Innovation, and Biz Dev @ The Second City where he’s hired and developed shows with Tina Fey, Stephen Colbert, Seth Meyers, Steve Carell, Keegan-Michael Key, Amy Poehler, and others. On top of this, he wrote the best-selling book "Yes, And" and hosts the "Getting to Yes, And" podcast for Second City and WGN Radio in Chicago.

Here’s a preview of the gold he offers up in today’s episode:

If you want a raise in 2023, take a page from Ted Lasso’s book and work on your soft skills.

Why saying “yes, but” is just like saying “no” with a top hat.

You’ll never understand everything going on in a room - that’s why selfless curiosity is mandatory.

When you have an Amy Poehler on your team, find their place and don’t waste their talent.

Nothing truly innovative looks like it should make sense - otherwise it wouldn’t be innovative.

You achieve authenticity through your fiascos - not your perfections.

Why building the pedestal first is only the illusion of progress.

Connect with Kelly on LinkedIn and Twitter

Must-read mentions from this episode:

Quit by Annie Duke

The Language Game by Morten H. Christiansen and Nick Chater

The Song of Significance by Seth Godin

Reculturing by Melissa Daimler