
Erin Diehl built a business around making it up as you go—literally. As founder of Improve It, she’s turning improv into a workplace superpower and failure into fuel for growth.
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A
Hi, everyone. Welcome to our show. Chief Change Officer, I'm Vince Chen, your ambitious human host. Our show is a modernist humility for change. Progressives in organizational and human transformation from around the world. Today's guest is Aaron deo, founder and CEO of ImproveIt, 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 Aaron, you are in the business of joy, but beyond joy. We also talked about failure. Aaron 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?
B
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, that was my first foray on earth. And then as I grew up, I fell in love with the stage. I was I 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. Thence. 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 9 to 5 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 9 to 5 and then 6 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 used 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.
A
He mentioned as a teenager you were determined to become a talk show host. I find that intriguing, honestly. Most people in the 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 of my 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?
B
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 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 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 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.
A
So you 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 elevated pitch, this should be the first sentence out of your mouth. Hey, I'm in the business of joy.
B
Thank you, Vince. Yes.
A
Let's say we are at a party. I introduce myself to you. Hey, I'm Vince. You reply, I'm Aaron. Nice to meet you. Then I ask, what business are you in? And you hit me with, oh, I'm in the business of joid. Instant curiosity triggered. Naturally, I would say, oh, tell me more about that is such a great icebreaker.
B
I love it. Okay, noted. It was heard here first. I will every time.
A
So no problem quoting that. I'm in the business of Georg and hey, I got it on record now, I promise I won't charge you for copyright yet. But seriously, something else fascinating from a history of 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?
B
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 2 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 it's 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 and to your day to 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 non verbal. Two activities with a debrief and a partner activity at the end we do affects 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, Ben's 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 this 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 elearning 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 our 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 ask. And so we created it with the client's challenges in mind and just kept listening and building to get us to this point. Point.
A
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?
B
Yeah, such a good question. So we tell clients at the get go, we don't measure your roi, we measure your roof, 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, and 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 off site in 2025 and then not hire us again till 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 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 able to 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. So 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 talk 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 soft skills are much more hard 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 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.
A
I understand one of your key workshops focuses on failure and you even coined the term fellow fluellencers, 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.
B
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. 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.
A
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, 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.
Chief Change Officer Podcast Episode #389: Erin Diehl – From Talk Show Dreams to a Business Built on Bombing — Part One
Release Date: May 25, 2025
In Episode #389 of the Chief Change Officer podcast, host Vince Chan engages in a profound conversation with Erin Diehl, the founder and CEO of ImproveIt. This two-part series delves deep into Erin's unique journey from aspiring talk show host to developing a business that leverages improvisation to foster growth, joy, and resilience within organizations. The discussion touches on themes of passion, failure, personal growth, and innovative business strategies.
Erin Diehl begins by sharing her vibrant entry into the world, describing, “[...] my mom said I came out of the womb dancing and saying, hello world, I'm here” ([02:12]). This early display of creativity foreshadowed her lifelong passion for performance and communication. From a young age, Erin was enamored with the idea of being on stage—dancing, acting, and even singing, albeit “not well.”
Her aspiration crystallized during her teenage years when she was inspired by Oprah Winfrey. As Erin recounts, watching Oprah’s compassionate and empathetic approach on television ignited her desire to “be a talk show host like Oprah” ([06:15]). This ambition drove her to pursue a degree in communications at Clemson University, despite the limited resources and opportunities for aspiring talk show hosts in the early 2000s.
Erin’s journey took a pivotal turn when she moved to Chicago, the heartland of improv comedy. Immersing herself in classes at renowned institutions like Second City, Improv Olympic, and The Annoyance, she discovered the profound impact of improvisational skills on personal and professional development. “I kept coming back to improv,” Erin explains, emphasizing how these classes not only honed her performance skills but also enhanced her abilities in listening, empathy, and quick thinking ([02:12]).
Balancing a demanding job in business development and her passion for improv, Erin noticed a seamless integration of her stage skills into her professional life. This synergy led her to experiment with using improv as a tool for team building and trust development, eventually catching the attention of major clients like United Airlines. “The 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…” Erin reflects on her early workshops ([10:26]).
In 2014, recognizing her calling to combine joy with professional development, Erin founded ImproveIt—an improv-infused talent development company aimed at fostering leadership, self-improvement, and team cohesion through play. Erin succinctly captures the essence of her mission: “I'm in the business of joy” ([08:28]).
ImproveIt’s methodology is meticulously crafted to address specific client needs. Erin outlines a structured approach where each workshop begins with understanding the client’s objectives and challenges. Utilizing a blend of pre-work components, interactive improv activities, and comprehensive debriefs, ImproveIt ensures that participants internalize and apply the lessons learned. A notable workshop example focused on “effective communication” demonstrates this process, blending verbal and non-verbal skills with active listening exercises to create actionable insights for participants ([10:26]).
Erin provides an in-depth look into the framework of ImproveIt’s workshops. Each session is built around an overarching thesis statement, broken down into manageable segments with targeted improv activities. For instance, in the “effective communication” workshop, activities are designed to enhance both what participants say and how they say it, ultimately affecting how others listen and respond ([10:26]).
A unique and engaging element of ImproveIt’s sessions is the incorporation of the “chicken dance,” a playful exercise that has successfully engaged over 40,000 people. This activity not only breaks the ice but also crowns an “improv chicken champion,” celebrating those who step out of their comfort zones and embody the workshop’s spirit ([10:26]).
Furthermore, each workshop is complemented by an e-learning component, ensuring that the lessons extend beyond the in-person or virtual sessions. This multi-faceted approach reinforces learning through continuous engagement over the following weeks ([10:26]).
When discussing the effectiveness of her programs, Erin emphasizes the importance of “Return on Objective (ROO)” over traditional ROI metrics. By aligning workshops with specific client goals and conducting thorough pre-engagement consultations, ImproveIt ensures that each session is tailored to meet distinct organizational needs ([16:05]).
Erin elaborates on the different levels of engagement:
These structured programs allow ImproveIt to deliver measurable and lasting impact, fostering higher collaboration, enhanced problem-solving, and a positive organizational culture rooted in psychological safety ([16:21]).
A central theme of Erin’s philosophy is the constructive role of failure in personal and professional growth. Referring to herself as a “fail flu lancer,” Erin integrates the concept of failure with influence, viewing setbacks as essential steps toward success. She introduces her keynote, “F Words at Work,” which explores how frequent failure lays the foundation for achieving fundamental success ([19:21]).
Although Part One of the episode sets the stage for this discussion, Erin hints at sharing personal stories and methodologies for navigating failure in the upcoming segment. This approach underscores the transformative power of embracing and learning from failures, a core principle that fuels both her personal development and her business ethos ([19:21]).
As the conversation wraps up, Vince anticipates continued insights in Part Two, where Erin promises to delve deeper into her personal experiences with failure and introduce her method of “move on”—a strategy for overcoming and rising above failures. Listeners are encouraged to subscribe and stay tuned for the next installment of this enlightening series ([20:15]).
Notable Quotes:
Final Thoughts
Episode #389 of Chief Change Officer offers a compelling narrative of Erin Diehl’s journey from aspiring talk show host to pioneering a business that harnesses the power of improv to drive organizational transformation. Her story is a testament to the importance of aligning passion with purpose, embracing failure as a catalyst for growth, and continually innovating to meet the evolving needs of clients. As Erin prepares to share more about her personal encounters with failure and her strategies for overcoming them in Part Two, listeners can expect to gain invaluable insights into building resilience and fostering a culture of joy and collaboration within their own organizations.
Join the conversation and stay updated with more transformative stories by following Chief Change Officer on LinkedIn, Apple Podcasts, Spotify, and YouTube @chiefchangeofficer.