Kelly Leonard

RolesProducer

Kelly Leonard is an American comedy executive, author, and applied improvisation advocate who has shaped The Second City for over three decades. Starting in the company's kitchen in 1988, he rose to Executive Vice President and President of Second City Theatricals, overseeing the hiring of Tina Fey, Stephen Colbert, Amy Poehler, and Steve Carell. He co-authored Yes, And: How Improvisation Reverses 'No, But' Thinking and Improves Creativity and Collaboration (2015) with Tom Yorton and hosts the Getting to Yes, And podcast. Since 2017, he has served as Executive Director of Insights and Applied Improvisation at Second City Works.

Leonard joined The Second City in 1988, beginning in the kitchen before moving into production roles. He became a producer in 1992 and eventually rose to Executive Vice President and President of Second City Theatricals, making him one of the most influential figures in the organization's modern history. In these roles, he oversaw the creation of hundreds of original revues across Second City's stages.

Leonard was directly responsible for hiring performers who would become defining figures in American comedy. His casting decisions brought Tina Fey, Stephen Colbert, Steve Carell, Amy Poehler, Adam McKay, Seth Meyers, Rachel Dratch, Jason Sudeikis, Keegan-Michael Key, and Amy Sedaris to The Second City's stages. This record of talent identification represents one of the most consequential scouting runs in comedy history, as many of these performers went on to reshape television, film, and political satire.

In 2015, Leonard co-authored Yes, And: How Improvisation Reverses 'No, But' Thinking and Improves Creativity and Collaboration with Tom Yorton, published by Harper Collins. The book applied Second City's improvisational principles to business, education, and personal development. Michael Lewis praised it in Vanity Fair as "an excellent guide to the lessons that have bubbled up in Second City's improv workshops." The book became a bestseller and established Leonard as a leading voice in the applied improvisation movement.

Also in 2015, Leonard stepped down from day-to-day management of The Second City's theatrical operations. In 2016, he became Vice President of Creative Strategy, Innovation and Business Development. In 2017, he took on the role of Executive Director of Insights and Applied Improvisation at Second City Works, the organization's corporate training and applied improv division.

In this capacity, Leonard co-leads a collaborative initiative with the University of Chicago Booth School of Business examining behavioral science through the lens of improvisation. This academic partnership brings empirical research methods to the study of how improvisational techniques affect creativity, collaboration, and decision-making in organizational contexts.

Leonard hosts the Getting to Yes, And podcast for Second City Works and WGN Radio, featuring conversations with leaders across business, psychology, and the arts. Guests have included Brene Brown, Adam Grant, Michael Lewis, and Dan Pink. The podcast extends the principles articulated in his book into ongoing public discourse about applied improvisation.

As a keynote speaker, Leonard has presented at the Aspen Ideas Festival, the Code Conference, TEDx Broadway, the Chicago Ideas Festival, and the Stanford Graduate School of Business, as well as for corporations including Coca-Cola, Microsoft, Twitter, Memorial Sloan Kettering, and DDB Worldwide.

Historical Context

Leonard's career at The Second City spans the organization's transformation from a primarily theatrical institution into a multi-platform comedy enterprise with significant corporate training operations. When he arrived in 1988, Second City was already a legendary name in comedy, but the organization's business model remained centered on its Chicago and Toronto stages. Over the following decades, Leonard helped expand its reach through touring companies, additional performance venues, and the development of Second City Works as a corporate training arm.

His early years at The Second City coincided with one of the institution's richest talent periods. The performers he hired in the 1990s and early 2000s formed a cohort that would dominate American comedy for decades. Fey and Poehler went on to anchor Saturday Night Live and become two of the most influential women in comedy history. Colbert created one of television's most acclaimed political satire programs. Carell became a leading film comedy star. McKay transitioned from SNL head writer to Oscar-winning filmmaker. Leonard's ability to identify this level of talent consistently across multiple casting cycles remains one of the most remarkable executive achievements in comedy history.

His transition from theatrical management to applied improvisation leadership in 2015-2017 mirrored a broader shift in the improv world. As the applied improv movement gained momentum in corporate, educational, and therapeutic settings, Leonard positioned himself and Second City at the intersection of improvisational practice and behavioral science. The partnership with the University of Chicago Booth School of Business represented a new frontier: subjecting the intuitive benefits improvisers had long claimed to rigorous academic scrutiny. This collaboration produced research examining how improvisational training affects listening skills, creative confidence, and collaborative problem-solving in professional settings.

Teaching Philosophy

Leonard's philosophy, articulated in Yes, And and expanded through his podcast and speaking engagements, centers on the idea that improvisational principles are not merely performance techniques but fundamental cognitive and social tools. The book's core argument is that the yes-and mindset, which requires accepting and building on others' contributions, counteracts the reflexive no-but thinking that stifles creativity in organizations. His work with the Booth School of Business seeks to ground this intuition in empirical evidence, studying how improvisational exercises measurably affect group dynamics, creative output, and psychological safety. Leonard's approach treats improvisation as a technology for human interaction rather than simply an art form, positioning Second City's decades of stage wisdom as a resource for organizational transformation.

Legacy

Leonard's influence on American comedy operates on two distinct levels. As a talent scout and theatrical executive, his hiring decisions at The Second City helped launch careers that reshaped Saturday Night Live, late-night television, and Hollywood comedy for a generation. The performers he brought to Second City's stages went on to win Emmy Awards, Academy Awards, and Peabody Awards, creating a body of work that defined American comedy in the early twenty-first century. His three-decade tenure made him one of the longest-serving and most consequential executives in the history of institutional improv.

As an applied improv evangelist, his book, podcast, and academic partnerships have made the case that improvisational training belongs in boardrooms, classrooms, and research labs as much as on comedy stages. Yes, And became one of the most widely cited texts in the applied improvisation field, translating Second City's institutional knowledge into a framework accessible to business leaders and educators with no comedy background. His role in building Second City Works into a major corporate training operation helped establish applied improv as a legitimate professional discipline rather than a novelty team-building exercise. The Getting to Yes, And podcast extended this influence by creating an ongoing public platform for conversations about how improvisational principles apply across disciplines, from psychology and neuroscience to business strategy and creative leadership.