Yes, And

What would happen if you approached life not as a series of instructions to follow, but as a performance—one where you and everyone around you were constantly co-creating in real time? In Yes, And, Kelly Leonard and Tom Yorton of The Second City argue that the principles of improvisation are not just for actors on a stage—they’re essential for anyone who wants to be more creative, more collaborative, and more adaptive in work and life. Drawing on decades of experience running the world’s most famous comedy institution, the authors show that the same techniques that helped launch the careers of Tina Fey, Stephen Colbert, Bill Murray, and Steve Carell can also help you tackle business challenges, lead teams, and even handle personal setbacks with insight and humor.

Leonard and Yorton contend that improvisational thinking isn’t about being funny or reckless; it’s about being fully present, listening deeply, and being willing to build on what others offer you. In their world, creativity thrives in environments where people say “Yes, And” rather than “No, But”; where failure is treated as learning; and where listening becomes an act of empathy. Improv, they argue, is like yoga for your professional and emotional intelligence—a practice that strengthens flexibility, resilience, and collaboration.

The Second City Experiment

Founded in 1959 in Chicago, The Second City began as a radical experiment: a theater that used improvisation to satirize politics, relationships, and the absurdities of everyday life. What started in a small cabaret above a Chinese laundry grew into the premier training ground for generations of comic talent. Beyond the laughs, however, Leonard and Yorton discovered something profound. The same collaborative methods that created breakthrough comedy also nurtured innovation, empathy, and trust—skills now recognized as vital in 21st-century organizations like Google and Nike. Businesses, they argue, are essentially acts of improvisation: despite plans and forecasts, success depends on how well people respond to the unexpected.

Why Improvisation Matters Beyond the Stage

Improvisation offers something that traditional business education often neglects: the ability to navigate ambiguity with grace. Where MBA programs emphasize analysis and control, improv emphasizes adaptation and connection. For instance, at Major League Baseball’s rookie camp, Second City actors help young athletes build communication and self-awareness by role-playing difficult scenarios. The goal isn’t to rehearse lines but to learn how to think on your feet, listen for emotional subtext, and respond authentically.

As the authors note, this is increasingly essential in a business world that values emotional intelligence as much as technical expertise. Modern leaders must “follow the follower”—allowing status to shift fluidly within teams based on expertise rather than hierarchy. Improvisers understand how to do this instinctively, creating what the authors call an “ensemble,” a group that performs better together than any one member could alone.

Seven Elements of Improv That Transform Work

Leonard and Yorton identify seven core elements of their craft that can transform work and leadership: Yes, And (accepting and building on ideas); ensemble (a shared accountability that lifts everyone); co-creation (dialogue over monologue); authenticity (truth and irreverence balanced with respect); failure (redefining mistakes as creative opportunities); follow the follower (dynamic, inclusive leadership); and listening (the muscle that powers all the rest). Each element becomes a lens for reimagining everyday challenges—from brainstorming sessions and client meetings to how you handle conflict or lead change.

Throughout Yes, And, the authors interweave stories from The Second City and its collaborations with organizations like Farmers Insurance, Norwegian Cruise Line, and the U.S. Department of Education. Whether navigating political sensitivities or corporate compliance training, they demonstrate that laughter—rooted in truth and connection—can defuse fear, build trust, and accelerate innovation. What’s radical about their message is that these soft skills aren’t secondary; they’re the foundation of real creativity.

Improvisation as a Mindset

Ultimately, Leonard and Yorton ask you to stop seeing creativity as a product of genius and start seeing it as a social process. You don’t need to be witty or extroverted to improvise well; you just need to listen, affirm, and add. When people adopt this mindset, something magical happens: meetings become dialogues; mistakes become discoveries; and organizations evolve to be more human, inventive, and resilient.

Improvisation isn’t about pretending without rules—it’s about collaboration with trust. And once you say “Yes, And” to life, you start rewriting the script in ways that make work less fearful and far more creative.

In the chapters that follow, Leonard and Yorton explore how these improv principles can transform everything from team building to leadership, from confronting failure to fostering authentic communication. Their invitation is simple yet profound: stop rehearsing, start connecting, and discover what’s possible when you live—and lead—like an improviser.

The phrase “Yes, And” lies at the core of improvisation—and of Yes, And the book itself. These two little words encapsulate a radical way of approaching creativity, communication, and problem solving. Instead of rejecting ideas or waiting to be right, you learn to affirm what others offer and add something new. The authors show how this simple linguistic shift transforms not only scenes onstage but also relationships in the workplace.

Affirm and Build

In improv, when one performer says, “Look at all these stars,” her partner responds, “Yes, and we must be on the moon!”—not “No, it’s daytime.” The second response kills momentum; the first builds something together. This is how scenes—and trust—are built. In business, people tend to say “Yes, but…” as a polite way of rejecting ideas, clinging to control. Leonard and Yorton argue that this reflex shuts down innovation faster than any market threat ever could.

Katie, a shy HR manager featured in the book, exemplifies the transformation that happens when you internalize “Yes, And.” Tasked with rotating into new teams every few months, she dreaded networking. Through improv exercises like “Exposure” and “Doctor Know-It-All,” she learned to replace self-consciousness with curiosity, affirming others’ ideas rather than worrying how she came across. Soon, even her reserved demeanor became an asset—her deep listening drew others in. This is Yes, And in action: turning fear into engagement.

Application at Work

The authors show how “Yes, And” reshapes critical business conversations. In coaching sessions, it allows leaders to acknowledge mistakes without defensiveness: “Yes, we lost the account—and here’s what we learned.” In brainstorming, it keeps teams from shutting down odd ideas too early, often leading to breakthroughs (as when a mattress company turned a dull product into a sexy viral rap video). In crisis management, it converts panic into momentum—most memorably when The Second City created the sold-out Rod Blagojevich Superstar during Chicago’s gubernatorial scandal, by saying yes to a risky idea even in the middle of a spending freeze.

Leonard and Yorton also warn of the misuse of “Yes, And”—fake agreement or manipulative positivity. As Tina Fey’s parody scene “Yes, And” shows, people sometimes use apparent agreement to dominate or undermine others. True “Yes, And” demands sincerity: it’s not a verbal trick but a disciplined practice of generosity and shared ownership.

Why It Works

The secret power of “Yes, And” lies in its social psychology. It creates safety, inviting contribution and risk-taking. It combats what behavioral economists call “loss aversion”—the fear of being wrong. And it transforms competition into co-creation. The authors summarize this in the improv axiom “Bring a brick, not a cathedral.” Each person’s small idea matters because it helps construct something larger together. That’s how trust becomes culture and culture generates innovation.

“Yes, And” is the language of possibility. It trains teams to see contributions not as threats but as invitations. When everyone builds, no one blocks—and that’s where creativity takes off.

In a world where most meetings are exercises in polite negation, adopting “Yes, And” is a rebellious act. But as Leonard and Yorton show, it’s also the most practical: it keeps ideas alive long enough to surprise you. Whether you’re scripting a sketch, managing a brand crisis, or reimagining your career, “Yes, And” offers a simple prompt to start transforming “no way” into “what if?”

While businesses love to talk about teams, Leonard and Yorton prefer the word ensemble. A team, they argue, competes against others; an ensemble collaborates for shared creation. The difference is subtle but crucial. Ensembles are built on trust, inclusion, and shared accountability—exactly what The Second City depends on for every performance.

The Ensemble Effect

In improv, stars like Bill Murray or Tina Fey didn’t shine because they outperformed others; they thrived because their ensembles elevated them. An ensemble transforms individual talent into group intelligence. History proves this works beyond comedy: from Phil Jackson’s Chicago Bulls to collaborative ventures in Silicon Valley like Lightbank, innovation flourishes when people build on one another rather than compete for spotlight.

The authors describe how diversity fuels this synergy. Early Second City casts were overwhelmingly white and male, limiting the range of stories they could tell. After the 1992 Los Angeles riots, Andrew Alexander launched the Second City Outreach Program to diversify its stages. That choice not only enriched artistic expression but deepened the company’s cultural relevance—enabling performers like Keegan-Michael Key to create pointed satire about race and identity that audiences connected with profoundly.

Practicing Ensemble Thinking

The authors recommend exercises like Mirror (observing a partner’s movements until both move as one) and Give and Take (learning when to hold focus and when to pass it). These games teach presence and humility. You can apply the same principles in meetings—listen before speaking, notice who is dominating the floor, and consciously share attention. As longtime Second City teacher Sheldon Patinkin said, “An ensemble is only as good as its ability to compensate for its weakest member.” In business terms, that translates into responsibility for each other’s success, not just one’s own.

Letting Go of Being Right

A healthy ensemble demands surrendering the need to be right—a major barrier in hierarchical organizations. The authors recount a workshop with a cultural institution plagued by one domineering executive, “Jim,” whose inability to listen made his team miserable. Through improv exercises where he had to assume low status and say “Yes, And” to peers, Jim realized how toxic his dominance was. He hated it—but the lesson stuck. Some “Jims” can’t adapt; others, like the tech CEO who literally demoted himself after an improv awakening, remake entire organizations for the better.

An ensemble is not the absence of leadership—it’s leadership distributed. Everyone alternates between guiding and supporting, creating flow rather than friction.

By replacing competition with collaboration and control with curiosity, you move from a team that merely functions to an ensemble that creates. In such a group, you don’t win by being right—you win by making each other look good.

At The Second City, every laugh is a form of audience feedback. Leonard and Yorton use this as a model for co-creation—the practice of developing ideas, products, or experiences in partnership with your audience. Instead of dictating solutions, you invite real-time participation, much like how an improv show emerges from audience suggestions.

Dialogue Over Monologue

In one show, a scene where Superman rolled onstage in a wheelchair initially shocked audiences—until the ensemble reworked it into a song about vulnerability and heroism. The piece became powerful precisely because the performers listened to the crowd. Leonard calls this process “finding the idea, not your idea.” Great innovation often comes from ceding ownership, a principle that applies equally to brands opening social media dialogues or companies running customer hackathons.

Fear, however, kills co-creation. The authors list its common disguises: asking endless questions instead of acting, masking insecurity with aggression, yelling to dominate, or waffling to avoid decisions. They note that these behaviors—common in workplaces—mirror how fearful improvisers sabotage scenes. Overcoming them means creating psychological safety and practicing decisive, collaborative listening.

Business Lessons from the Stage

From Tony Hendra’s improv with John Belushi to today’s Twitter-based “Clorox Ick Awards,” co-creation works because it channels human truth. In the Clorox campaign, parents tweeted their real-life messes while Second City actors performed them live online. This collective storytelling turned a cleaning brand into a platform for humor and authenticity—drawing 160 million social impressions and proving that engagement beats perfection.

The same principle guided Second City’s R&D process: the Improv Set. After each show, actors test new material in a free, late-night session. Because the stakes are low, the creativity is high. The audience knows it might see brilliance or disaster, and that mutual acceptance makes experimentation possible. Companies can emulate this by building “safe-to-fail” venues for experimentation—like Chicago Tribune’s Trib Nation events, where journalists met readers in bars to discuss stories face-to-face, strengthening trust through informal transparency.

Co-creation turns customers into collaborators. When people help shape something, they invest in it. What begins as feedback becomes ownership.

Whether testing comedy or building a campaign, the lesson remains: abandon perfection, embrace participation. The future belongs to organizations that stop performing for their audiences and start improvising with them.

Change triggers fear—but comedy dissolves fear through truth. Leonard and Yorton argue that humor, when grounded in empathy, makes it easier for people and organizations to face uncomfortable realities. They draw on years of working with corporations and government agencies to show how laughter can open conversations that logic alone cannot.

The Anatomy of Humor

Comedy, writes Anne Libera of The Second City, requires three elements: recognition (we see ourselves in the joke), pain (something’s wrong), and distance (we feel safe enough to laugh). When a sketch about Bill and Hillary Clinton’s silent kitchen standoff played onstage, audiences laughed not just at politics but at their own relationships. That’s what makes comedy transformative—it connects you to a shared truth, then releases tension through laughter.

Laughing Through Transformation

The authors illustrate this with surprising corporate case studies. The U.S. Department of Education brought Second City in to ease tensions among superintendents and teachers’ unions. By playfully satirizing “perfect” systems like Finland’s, comedians helped officials acknowledge challenges without blame. Similarly, Norwegian Cruise Line invited Second City to make fun of its own inefficiencies—like cramped cabins and endless announcements—turning passenger frustration into communal amusement. Once people laughed, they stopped resisting and started engaging.

Respect, Not Reverence

One powerful insight from the book is the Respect/Revere Dynamic. Too many organizations revere their systems and heroes so completely they can’t question them. Respect allows dialogue; reverence breeds fear. The Second City’s famous staff roasts—where employees satirize leadership openly—helped spur real improvements, like expanding healthcare for part-timers. That’s comedy doing change management better than any memo.

Even the most conservative domains, like corporate compliance training, benefit from this approach. Through funny video shorts, Second City transformed tedious ethics modules into relatable scenarios. The humor grabbed attention, lowered defenses, and let serious messages land. As Leonard puts it, “The higher the stakes, the more you need comedy to make the conversation safe.”

“Before people will change behavior, they must change attitude—and before they change attitude, they must laugh.”

By balancing irreverence with respect, humor reintroduces humanity into business. It turns blame into insight and fear into possibility—precisely what every organization needs when facing change.

If success is applauded, failure is the standing ovation no one admits to needing. For Leonard and Yorton, failure isn’t an obstacle to creativity—it’s the raw material of it. They argue that repeated, visible, even spectacular failures are the price of constant innovation, whether in art, entrepreneurship, or relationships.

From Stage Bombs to Business Breakthroughs

At The Second City, failure is unavoidable. Late-night Improv Sets are free precisely because many sketches flop. From disastrous menu items (the “Royster Oyster” burger that caused food poisoning) to the flop of Serious Improv, the company’s history is a master class in resilience. Yet these missteps paved the way for triumphs like The Second City Guide to the Opera—a collaboration that began disastrously but finished in a sold-out performance with Renée Fleming and Patrick Stewart.

Leonard and Yorton outline six ways they intentionally “fail better”: in public (so learning is seen), together (so no one shoulders blame), fast (so momentum continues), free of judgment (so creativity flows), with confidence (trusting the process), and incrementally (bringing “bricks” instead of cathedrals). Each principle encourages a culture of experimentation rather than perfectionism.

Failing Forward in Organizational Culture

Progressive companies already follow similar logic. Basecamp conducts lighthearted “product roasts” to expose design flaws safely. Farmers Insurance co-creates humorous training videos that test new ideas without fear of corporate backlash. Both mirror Second City’s approach: treat creativity like science—hypothesize, test, laugh, repeat.

Failure also has a social dimension. Improv actors begin each show by saying, “I’ve got your back,” signaling mutual trust before stepping into the unknown. Businesses can mimic this ritual by normalizing risk and modeling humility from the top. When leaders share their own mistakes—like the tech founder who congratulated teams for lessons learned—failure evolves from shame into strategy.

To innovate is to fail publicly—because only when you risk embarrassment can you discover something that hasn’t been done before.

Failing well requires practice, patience, and play. Whether you’re an improv actor or a CEO, the trick isn’t to avoid mistakes—it’s to recover from them with style, humor, and collaboration. Fail early, fail often, and your eventual “Yes, And” will be stronger because of it.

Modern leadership, Leonard and Yorton argue, looks less like command-and-control and more like improv’s Follow the Follower. The idea—originating with Viola Spolin and echoed by management theorist Peter Drucker—suggests that leadership shifts dynamically within ensembles. Whoever has the knowledge or energy in the moment leads, while others support. Then roles switch again. This, they say, is how creativity—and modern business—actually work.

From Hierarchy to Ensemble

In Spolin’s exercise, everyone moves together, imitating subtle shifts until the group seems to share one mind. No one gives orders, yet coherence emerges. The authors apply this to The Second City’s own operations: directors decide when producers can observe rehearsals, giving creative teams autonomy without isolation. When trust replaces micromanagement, innovation accelerates. Andrew Alexander, Second City’s longtime producer, summed it up succinctly: “Build the sandbox, hire great people, and get the hell out of the way.”

This philosophy extends to their own missteps. When they examined ticketing policies, feedback from staff and consultants revealed hidden biases and outdated assumptions. By following the follower—listening to those closest to the customer—they redesigned systems that better served real audiences. It was a humbling lesson in how leadership sometimes means asking, not telling.

Leadership 2.0: Collaborative Power

Leonard and Yorton argue that improvisational leadership mirrors what social scientists now call “distributed” or “servant leadership.” Studies by Jack Zenger show that women, who often score higher in empathy and collaboration, embody these skills naturally. As leadership moves from dominance to facilitation, improvisation provides the perfect training. Betsy Myers, former COO of Obama’s campaign, calls this “leading with ‘What do you think?’ rather than ‘Here’s my answer.’”

Exercises like Who’s the Leader? or Silent Organization make these dynamics tangible. In silence, groups must align spontaneously, proving that clarity, empathy, and observation—not authority—are what truly coordinate people. As Twitter CEO Dick Costolo (also a Second City alum) notes, “Managers have to accept any initiation.” Listening, not defending, creates trust.

Follow the Follower is how modern leaders turn hierarchy into harmony. When power moves fluidly, so does creativity.

The take-home message is clear: leadership today means orchestrating, not dictating. When leaders learn to follow their teams just as teams follow them, organizations evolve from rigid scripts into living improvisations—agile, alert, and astonishingly effective.

Leonard and Yorton conclude with what might be the most underrated skill of all: listening. They call it a muscle—one that atrophies without deliberate exercise. True listening, they insist, is more than waiting for your turn to talk; it’s an act of empathy that powers every other improv skill. In a culture that prizes speaking over hearing, cultivating this discipline can change not just communication but relationships and leadership itself.

Listening Beyond Words

Improvisers learn early that scenes collapse when someone stops listening. When an actor mishears a partner’s line, chaos ensues—unless another actor rescues it by reframing the mistake (“So when did you learn my real identity?”). That alchemy—turning error into opportunity—depends on deep attention. In workshops like Repetition and Last Word Response, participants must echo or start with the final word of a partner’s sentence, forcing them to focus until the very end. The point isn’t the dialogue—it’s the awareness.

Listening to Intent

The authors highlight psychologist Paul Ekman’s research on microexpressions—the fleeting facial cues that reveal hidden emotions. Improv trains the same sensitivity. In gibberish exercises, participants communicate feelings through tone and gesture alone, learning to read what’s unsaid. Applied to business, listening for intent means catching what a client or employee truly feels before problems escalate. A Chicago ad agency, for instance, used these exercises to recover lost clients by finally hearing what politeness had hidden.

Listening also builds authenticity. It’s what helps you detect irony, empathy, or fear—the subtext where real truth resides. That’s why one of Second City’s guiding principles is “Make your partner look good.” It’s not just kindness—it’s focus. By lifting others, you uncover the story no one person could find alone.

Improvisation begins the moment you stop performing and start paying attention.

Through listening, improv reconnects us with what’s human in work: presence, humility, curiosity, and compassion. As Father Joe told comedian Tony Hendra, “The only way to know another person—or God—is to listen.” That’s also the only way, Leonard and Yorton remind us, to know ourselves.