Kelly Leonard Books
Kelly Leonard is Executive Director of Learning and Applied Improvisation at The Second City, where he has worked for over three decades.
Known for: Yes, And
Books by Kelly Leonard
Yes, And
What if the skill that makes great improvisers funny onstage could also make leaders wiser, teams more creative, and organizations more resilient? In Yes, And, Kelly Leonard and Tom Yorton argue that the core principle of improvisational theater—accepting what is offered and building on it—has profound relevance far beyond comedy. Drawing on decades of experience at The Second City, the legendary Chicago institution that launched generations of performers and trained countless organizations, the authors show how trust, listening, adaptability, and shared creation can become practical leadership tools. This is not a book about becoming a comedian. It is a book about learning to respond constructively in uncertain situations, support others’ ideas without losing judgment, and turn collaboration into a disciplined practice rather than a corporate slogan. Leonard and Yorton write with unusual authority: one shaped by years inside a world-famous improv theater, the other by experience translating those principles into business settings. The result is a leadership book that feels fresh, human, and immediately usable—especially for anyone trying to lead in a world where scripts rarely survive first contact with reality.
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The Second City and Collective Creativity
Innovation rarely begins with a lone genius; more often, it emerges from a group willing to make something together before anyone knows exactly what it is. That insight sits at the center of The Second City story. Founded in Chicago in 1959, The Second City developed a radically collaborative model ...
From Yes, And
Yes, And Begins With Deep Listening
Most people think improvisation is about being quick. In reality, it is about paying attention. The phrase “Yes, And” only works when the “yes” is genuine—when you have actually heard what another person is offering—and when the “and” adds something that moves the exchange forward. Without listening...
From Yes, And
Trust Makes Spontaneity Possible
People do their most original thinking when they feel safe enough to risk being imperfect. Improvisation depends on this truth. Onstage, performers cannot pause to calculate every move. They must trust that their partners will support them, that mistakes can be recovered from, and that no one is try...
From Yes, And
Failure Is Data, Not Disaster
The fear of failure shrinks people long before failure itself ever arrives. One of the most liberating ideas in Yes, And is that mistakes are not interruptions to the creative process; they are part of it. In improvisation, scenes go wrong all the time. Lines are missed, assumptions clash, and unexp...
From Yes, And
Status Shapes Every Human Interaction
People are always signaling status, whether they realize it or not. In improv, status is a powerful tool: characters can play high or low status through posture, tone, eye contact, and behavior, instantly changing the emotional dynamics of a scene. Leonard and Yorton show that the same forces operat...
From Yes, And
Innovation Requires Presence and Adaptability
The future rarely unfolds according to plan, which is why rigid leadership often fails exactly when it is needed most. Improvisers are trained to work without a script, but that does not make them chaotic. It makes them present. They stay alert to changing conditions, respond to what is actually hap...
From Yes, And
About Kelly Leonard
Kelly Leonard is Executive Director of Learning and Applied Improvisation at The Second City, where he has worked for over three decades.
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Kelly Leonard is Executive Director of Learning and Applied Improvisation at The Second City, where he has worked for over three decades.
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