Chief Change Officer
#160 From Talk Show Dreams to Improv CEO: Erin Diehl’s Business of Joy — Part One
Tue, 4 Feb 2025
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.” Connect with us: Host: Vince Chan | Guest: Erin Diehl --Chief Change Officer-- Change Ambitiously. Outgrow Yourself. Open a World of Deep Human Intelligence for Growth Progressives, Visionary Underdogs, Transformation Gurus & Bold Hearts. 6 Million+ All-Time Downloads. Reaching 80+ Countries Daily. Global Top 3% Podcast. Top 10 US Business. Top 1 US Careers. >>>100,000+ subscribers are outgrowing. Act Today.<<< --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.12 Million+ All-Time Downloads.Reaching 80+ Countries Daily.Global Top 3% Podcast.Top 10 US Business.Top 1 US Careers.>>>140,000+ are outgrowing. Act Today.<<<
Chapter 1: Who is Erin Diehl and what is her business about?
Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chan, your ambitious human host. Our show is a modernist community for change progressives in organizational and human transformation from around the world. Today's guest is Erin Deal, founder and CEO of Improved, a company that uses improv to help teams grow and thrive. Like me, she's also a top podcast host.
From a young age, Erin dreamed of becoming a talk show host. Why did she choose that path? And how did her journey lead her to combine improv and business? I told Erin, you are in the business of joy. But beyond joy, we also talked about failure. Erin calls herself a fail-flu-lancer. a blend of failure and influence.
This two-part series dives into her unique approach to joy, failure, growth, and learning. No more waiting. Let's get started. Welcome, Erin. Good morning to you. Where are you exactly?
Chapter 2: How did Erin Diehl's childhood dreams influence her career path?
Yes, I am in Charleston, South Carolina. It's morning for me. It's evening for you. So I'm having some coffee and just enjoying the start of the day. When I was born, my mom said I came out of the womb dancing and saying, hello world, I'm here. So that was my first foray on earth. And then as I grew up, I fell in love with the stage. I was a dancer, I was an actress. I sang but not well.
And I decided early on I wanted to be a talk show host. That was my goal then. And so I went to Clemson University and graduated with a degree in communications. And this was the early 2000s. So there wasn't a ton of... internet coaching or there wasn't a ton of opportunity for me to learn how to be a talk show host. So I said, where should I go?
Naturally, the home of Oprah Winfrey, my dream talk show host. So I moved to Chicago, started taking improv classes and really fell in love with it as an art form. And over the years, I did book some hosting things, but I kept coming back to improv. And finally, in my late 20s, I decided to stop traveling. I was doing a ton of traveling at the time.
take a nine to five job at a recruiting firm, which I had never done recruiting. And the job that I took was actually business development. So it was sales. And so I worked nine to five and then six to 10 every night. I took classes at the second city or improv Olympic or the annoyance, which are huge theaters in the U S and in Chicago.
Chapter 3: How did Erin combine improv with business?
And I just saw everything I was doing on stage really spill over into my workplace. I was becoming a better listener. I was more empathetic. I was thinking more quickly on my feet. And I knew that there was a connection between improv and the professional world. So at the time, one of my clients at this recruiting farm was United Airlines.
I asked my boss if I could pilot, pun intended, a workshop to United using improv. And of course they said yes. And the first couple of ones I did were for free. And then United said, we're going to pay you. And so my very first client was United Airlines. As time progressed, I knew that this was my calling.
Chapter 4: What was Erin Diehl's first big break in her business?
I knew I wanted it to be bigger than just me, so I left my full-time job and started Improve It in 2014. Improve It is an improv-infused talent development company for the new generation of work. We use improv to teach people how to lead teams, how to be the highest versions of themselves, but it's ultimately all through play, and we've been in business 10 years, and here we are.
You mentioned as a teenager, you were determined to become a talk show host. I find that intriguing. Honestly, most people in their teens or even in college don't really know what they want to do, let alone something as specific as hosting a talk show. I mean, when I tell people I set my sights on getting into business school and earning an MBA at age 15, they often say, seriously? At 15?
It seems so young to have such a focused goal. But back to you, why talk show host? I imagine some might dream of being a news anchor or getting into show business. But for you, what was it about talk show hosting that drew you in? Especially back then, before podcasts even existed, what was the story behind that ambition?
Yeah. Oh, you're so right. We didn't have podcasts. There wasn't Instagram. There wasn't even Facebook at the time. Truly, when I went to college, Facebook did not exist until I graduated. So here's what I can tell you. I just remember When I was 13 years old, I was homesick from school.
Chapter 5: Why did Erin Diehl want to become a talk show host?
I don't know if you remember back in the early 90s or late 90s, there was a catalog called Delia's and it had all these like girly pajamas. I had on like the rattiest pair of Delia's pajamas. I was sitting in my family's living room on this like old 90s floral couch and I was sick. I was homesick and the Oprah Winfrey show came on.
And I just remember watching it and watching how she made the people in the audience feel. And watching Oprah just be such a compassionate, empathetic, kind human to her guests and also really care about humanity. And so I sat up, sick as I was, and I said to my mom, I'm going to do that, mom. I'm going to be a talk show host like Oprah.
And I know that I have something to talk about, but what happened was in my early twenties and even going through my twenties, I didn't have really enough life experience to have a platform to talk about anything. I feel like I do. I didn't have the life experience that I do now.
Let me just say that, that, that I don't want to discount myself, but I feel like I needed more life experience to be able to.
have a voice and know my voice and own my voice and i just equate talk show hosting to almost like being a florist when you get flowers you're almost always happy and i thought about becoming a talk show host so i could bring joy to other people's lives whether it was through television whether it was through an audio platform like podcasting
It was always my goal to use my voice for good and to make people feel really good in my presence. And so that was the goal. I had no clue it was going to be improv as the change catalyst. I had no idea it was going to be improv as the teaching tool, but I just knew I wanted to help people and bring joy.
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Chapter 6: How did Erin's passion for joy shape her business approach?
So you're essentially in the business of joy. That's it, the short form. Not keynote speaker, not founder or CEO. If someone asks you for your elevator pitch, this should be the first sentence out of your mouth. Hey, I'm in the business of joy. Thank you, Vince. Yes. Let's say we're at a party. I introduce myself to you. Hey, I'm Vince. You reply, I'm Erin. Nice to meet you.
Then I ask, what business are you in? And you hit me with, oh, I'm in the business of joy. Instant curiosity triggered. Naturally, I would say, oh, tell me more about that. It's such a great icebreaker.
I love it. Okay, noted. It was heard here first. I will love you every time.
So no problem quoting that. I'm in the business of joy. And hey, I got it on record now. I promise I won't charge you for copyright yet. But seriously, something else fascinating from history is your first client. You mentioned you tried things out with United Airlines, UA, and eventually they pay you and everything took off from there. So what was that initial experiment with United like?
What exactly did you do? I mean, Today, your business, Business Improv, is this successful franchise. But let's rewind to the beginning. What was iPhone 1.0 version of your business? What did it look like back then?
Yeah, such a good question. To be honest with you, I don't remember. I think it was, I think it was something about team building and building trust, but it was my very, we barely had a, I didn't even have a logo. I just put slides together on a random slide deck and I said, okay, what do you want me to teach on?
And I put together just a very small one hour presentation using improv as the teaching tool. And I actually found video of myself doing this on my computer. I need to post that video because it's clearly from like 2013. I had no clue what I was doing, but all I can see in that picture, coming back to your word joy, is joy. I just felt so joyful doing it and teaching.
And I knew every time I got in front of a group of people that that I was there to serve them. And I have to tell you, when I am in front of a room of people, something comes over me. It's not necessarily me. I feel like I am talking through just this greater good, and I'm here to help the greater collective find joy in their day-to-day. And so...
For me, I watched that video back and it's not necessarily what I said. It's how I felt in that moment and that energy that was in that room. And just the feeling of watching somebody else trust themselves enough to gently guide themselves out of their comfort zone and being the teacher to help them do that was incredible. And so it was a high and I kept chasing that high and wanting to do more.
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