#271 Erin Diehl: Talk Show Dreams, Improv Realities — Part One

Part One.

Erin Diehl dreamed of being the next Oprah but ended up becoming the queen of corporate improv instead. Now the founder and CEO of Improve It, she helps teams laugh their way to better performance. A self-declared “failfluencer,” Erin turns every faceplant into a feature. In this two-part series, we dig into her journey, her joy-first philosophy, and why bombing on stage—or in life—might be the best thing that ever happened to you.

Key Highlights of Our Interview:

Improv Meets the Corporate World

“I didn’t plan to merge improv and business. But during my nine-to-five at a recruiting firm, my nights were dedicated to stages at Second City and ImprovOlympic. Suddenly, I saw how listening, empathy, and quick thinking from improv transformed my work life. The dots connected.”

United We Innovate

“Pitching an improv workshop to United Airlines was a gamble, but it paid off—literally. What started as a passion experiment became a calling when United became my first paying client. Improv wasn’t just for the stage anymore.”

The Teacher’s High

“That feeling of guiding someone toward growth is intoxicating. It’s a high I kept chasing, and the more I taught, the more I wanted to do it. Seeing others find joy became my own source of joy.”

From ROI to ROO: The Objective Shift

“We don’t measure ROI; we measure ROO—Return on Objective. Every engagement starts with a consult call to pinpoint your specific challenges and objectives, ensuring everything aligns with the participants’ needs.”

Connect with us:
Host: Vince Chan | Guest: Erin Diehl

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