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.

1. Introduction to Erin Diehl and Her Aspirations

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.

2. Transition from Talk Show Host to Embracing Improv

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]).

3. Founding ImproveIt: A Business Built on Joy and Improv

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]).

4. Workshop Structure and Client Engagement

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]).

5. Measuring Success: Return on Objective (ROO)

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:

• Culture Jumpstart: A single workshop designed to spark conversation and initiate change within a team.
• Culture Shift: A series of three workshops over a year, fostering ongoing behavioral change and deeper engagement.
• Culture Change: An extensive program comprising six engagements over two years, embedding improv principles into the organization's core values and daily operations ([16:21]).

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]).

6. Embracing Failure: Personal Insights and Professional Philosophy

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]).

7. Conclusion and What’s Next

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:

• Erin: “I'm in the business of joy.” ([08:28])
• Erin: “When you say what you don't say, affects how others listen and respond.” ([10:26])
• Erin: “We don't measure your ROI, we measure your ROO—the return on objective.” ([16:05])
• Erin: “The frequency of failure equals the fundamentals of success.” ([20:42])

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.

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