Chief Change Officer - #389 Erin Diehl: From Talk Show Dreams to a Business Built on Bombing — Part One

Episode Date: May 25, 2025

Before Erin Diehl was training Fortune 500 teams to think on their feet, she was juggling job fairs by day and Second City by night.In Part One, we go back to the origin story—how a recruiting job collided with a comedy stage and sparked a business idea no one saw coming. From cold pitching United Airlines with zero credentials to redefining ROI as “Return on Objective,” Erin shares how improv became her leadership laboratory. Along the way, we talk about joy, failure, and what really happens when you turn your side hustle into your full-time mission.Key Highlights of Our Interview:From Stage Lights to Slide Decks“I was working in recruiting by day and performing improv by night. Eventually, I realized improv wasn’t just funny—it was functional.”How Erin’s stagecraft became a corporate tool.United We Improv“My first client was United Airlines—and I didn’t even have a logo yet.”How one bold pitch turned into a paid pilot and a new career.In the Business of Joy“I just knew I wanted to help people and bring joy.”Why Erin sees her work as more than training—it’s emotional transformation.Forget ROI, Focus on ROO“We don’t measure ROI—we measure ROO: Return on Objective.”How Improve It tailors every session to real business outcomes.From Talk Show Dreams to Leadership Teams“I wanted to be Oprah. I ended up helping people lead better lives through improv.”The full-circle moment that turned childhood dreams into professional purpose.________________________Connect with us:Host: Vince Chan | Guest: Erin Diehl  --Chief Change Officer--Change Ambitiously. Outgrow Yourself.Open a World of Expansive Human Intelligencefor Transformation Gurus, Black Sheep,Unsung Visionaries & Bold Hearts.EdTech Leadership Awards 2025 Finalist.18 Million+ All-Time Downloads.80+ Countries Reached Daily.Global Top 1.5% Podcast.Top 10 US Business.Top 1 US Careers.>>>170,000+ are outgrowing. Act Today.<<<

Hi, everyone. Welcome to our show, Chief Change Officer. I'm Vince Chen, your ambitious human host. Oshul is a modernist community for change progressives in organizational and human transformation from around the world. Today's guest is Aaron Deal, founder and CEO of Improve It, a company that uses improv to help teams grow and thrive.

Like me, she's also a talk 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 talk about failure. Erin calls herself a cell flu-lenzer, 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. Welcome, Errand. Good morning to you. Where are you exactly? 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 US

and in Chicago. And I just saw everything I was doing on stage really spill over into my work life. 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. 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, one five, 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. 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 radiest 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 home sick 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 gonna do that mom. I'm gonna be a talk show host like Oprah. And I know that I have something to talk about, but what happened was in my early 20s and even going through my 20s, 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. Not 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 Codcasting, 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 gonna be improv as the teaching tool but I just knew I wanted to help people and bring joy.

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 pledge, 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. Such a great icebreaker.

I love it. Okay, noted. It was heard here first. I will get 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 your history is your first client. You mentioned you tried things out with United Airlines UA, and eventually they pay you and everything top 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 Eiffel 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 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 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. So here's just blanket how we work. When a client comes to us, we will get really specific on what are you hoping to achieve?

What are your objectives? And then what challenges are you having? Over time, we've developed 10 different workshops that can host up to 100 people. And each workshop has a pre-work component with a video that shows them how not to do the skill that we're going to train them on. So there's comedy there.

It's about a two to three minute video. And then it guides the participant, these are for the participants, to a survey. And in that survey, we ask them their challenges and objectives. And so we take what the client says and what the participants say, we marry it together, and we bring it to this in-person or virtual training. And so let's just use effective communication as an example.

This is one of our most popular workshops. So every workshop has an overarching thesis statement to it. And then we break down that thesis statement and to chunks, most of the time, three to four chunks. And in those chunks, we do one to two improv-based activities. So the thesis statement for effective communication is what you say and what you don't say

affects how others listen and respond. So that first piece, we're doing two activities about what you say, your tone, your verbal tone, your written tone. We're doing two activities. They're high energy, you're standing on your feet, you're interacting with those around you. And after each activity, there's a debrief. And in that debrief is what we call the method to our madness.

That's where the magic happens, where we take what we just did, we put it into context, into your day to day day and help you think differently about how you're communicating, how you're using tone. And then we do a separate activity at the end of every two, which is we ask them to take what we've just talked about as the larger group and put it into context in their role because we really want them to get specific and bringing it back to their organization. So then we go to the next piece, which is what you don't say, which is all about nonverbal two activities with a debrief and a partner activity at the end. We do effects how others listen.

So two activities about active listening and then a debrief and then the partner activity. And then finally, how all of this affects people, the way people respond. We do two activities there, and then we wrap up everything with a key takeaway, which I will tell you, Vince, one thing that sets us apart is that we have successfully coerced over 40,000 people to chicken dance.

So in our workshops, whenever you hear the word improv, we chicken dance. And at the end, when we do our key takeaways, we crown an improv chicken champion. This is somebody who has gotten out of their comfort zone, given their all. And we have witnessed just being above and beyond the most enthusiastic person in the room. We celebrate that person. We do the key takeaways, and then we round with something we call the circle of yes, which is just this really high vibe, positive moment where we give each other praise, and then we give love to that chicken champion

and we end the session. And then after every workshop, we have an e-learning course built in conjunction with each workshop that then takes what we've done in the session and continue to learning for Monday, Wednesday, Friday for the next three weeks and the lessons get sent to them via email. So it's really robust. We are professional development first and foremost, improv is the teaching tool, but we have 10 of those experiences, not to mention our keynotes, book clubs, all of that.

So we really developed a lot of material over the past 10 years, and we're actually getting ready to come up with some fresh new ideas in 2025 that I'm super excited about. The everything that was built on client-esque. And so we created it with the client's challenges in mind and just kept listening and building to get us to this point. What are your key performance indicators?

How do you measure success in your business? And just as importantly, how do you identify areas for improvement? Yeah, such a good question. So we tell clients at the get-go, we don't measure your ROI, we measure your ROO, your return on objective. So that's why we're getting super specific with clients in that upcoming call. We have a consult call prior to every engagement where we make sure we nail down their challenges and objectives and pair those with the participants. So in the way we work with clients is threefold.

We have something, the first one is just a one and done workshop. We call it a culture jumpstart. So you might use this for a team offsite in 2025 and then not hire us again until 2027. That's a culture jumpstart. So in that one training session, we're not going to be able to change the course of your culture, but we're going to be able to change the course of your culture, but we're going to be able to be a conversation starter. And then the second way is something that we call a culture shift.

So that is three workshops over the course of one year, where we are guiding participants, building off of what we learned in the last session and continuing the conversation. And that we're able to measure some behavioral change over time. We're actually just see the results because we're still working together. The third way is called culture change, and I know you love this word, culture change. So that's six engagements over the course of two years. And that is we allow people to see that culture change over time. We're actually able to get in there,

integrate what we've done with their core values. For example, American Marketing Association was a client of ours in the very beginning, and we worked with them, what we call culture change, and over time, they actually integrated one of our core values, which is yes and, into their core values, and it was prominent every single place in their office,

in their meeting rooms, and it was a core tenet of how they operate. So that's really over time, how we can build and change cultures, have the conversation shift to more meaningful behavioral change. With the culture jumpstart, it is a conversation starter, but that return on objective is measured

not only from the participants with a survey at the end, but also from the client participant or the client who we've worked with I should say. And we talked with them after to make sure that we hit the objectives, it was what they were looking for, and talk about ways that we could improve it pun intended, which is our name, in the future. So, its soft skills are much more harder to measure, but ultimately what you are getting is higher collaboration, less frequent problem solving because people are coming up with solutions versus problems. You get more people interacting and cross collaborating with each other. And it overall creates this sense of positivity,

which is psychological safety at its core. So that's what we're aiming to do, is to bring this positive experience to your organization. How you take it and run with it is left to you if we don't work together over a series of time. I understand one of your key workshops focuses on failure, and you even coined the term, Foul Flu Lensers, a blend of failure and influencers. I love to dive into this topic, but from a personal perspective.

Could you share your own experiences with failure? Not so much the workshops you facilitate or the lessons you teach, but your personal journey. How you've dealt with, navigated, and grown from failure over time. If you like, feel free to share specific stories and give us an overview of your journey with failure. Either way works. Yeah, so this is actually a keynote that I do called F-words at Work. And there's no swearing, Vince. Okay, there's no swearing. Spo, okay? There's no swearing.

Spoiler alert, the F words are all about failure plus the frequency of failure equals the fundamentals of success. And truly, the reason I even created this is because I was living a crash course myself in failure. Tomorrow in part two, Erin will continue her story of failure. Tomorrow in part two, Erin will continue her story of failure. And she comes up with a magical way of navigating and rising above the failure experience.

She called this method Move On. Come back tomorrow and learn how to move on. Thank you so much for joining us today. If you like what you heard, don't forget to subscribe to our show, leave us top-rated reviews, check out our website, and follow me on social media. I'm Vince Chen, your ambitious human host. Until next time, take care.