Part One.
Meet Erin Diehl, a woman who turned “winging it” into a career strategy. She’s the founder and CEO of Improve It, a company that uses improv to help teams thrive.
As a kid, Erin dreamed of being a talk show host. Instead, she became a top podcast host and business leader, blending humor and learning to help others grow. She calls herself a failfluencer—because, in her world, failure isn’t an end, it’s a punchline and a lesson.
In this two-part series, we explore Erin’s journey, her philosophy on joy, and why failing might just be your best career move yet.
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.”
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Host: Vince Chan | Guest: Erin Diehl
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