Five Improv-Inspired Practices for Leading with Flexibility and Trust from Dan Klein

From saying "oh good" to shooting for average, this episode of How We Future with Lisa Kay Solomon celebrates the power of play, presence, and generosity in uncertain times

MENLO PARK, Calif., Oct. 28, 2025 /PRNewswire/ -- In a world where uncertainty is the only constant, improv may be the ultimate leadership skill.

On How We Future with Lisa Kay Solomon, improviser and Stanford lecturer Dan Klein reveals how the essential skills of improv—listening, accepting, adapting, and building together in real time—can help anyone strengthen creativity, connection, and resilience.

For more than twenty years, Klein has taught improvisation at Stanford, helping students and teams replace perfectionism with play. "When you celebrate failure loudly enough," he says, "you stop fearing it." His teaching reaches far beyond the stage: it's about responding to whatever comes your way with flexibility, empathy, and courage.

At a moment when pressure, performance, and perfection dominate daily life, this conversation offers an antidote: treat everyday uncertainty as rehearsal for the future.

Klein's approach turns big improv ideas into simple, real-world habits—five moves that help you meet change with curiosity instead of control:

1. Shoot for average and fail cheerfully.
Klein begins every class by telling his Stanford students, "Your job is to shoot for average and fail cheerfully." It's the opposite of what they expect—and exactly what they need. "So many students have internalized this pressure in a way that it's not sustainable," he says. "This mindset becomes a release valve. It cracks the armor, to let them reveal the shielded protection."

2. Celebrate failure—loudly.
When a scene falls apart, improvisers cheer. The goal isn't to avoid mistakes—it's to create safety. "If we can celebrate failure, not just accept it, but celebrate it over the top triumphantly, then things shift," Klein explains.

3. The 'Oh, Good' Principle.
 Whatever happens—a curveball, a surprise, an obstacle—try saying, "Oh, good." It transforms resistance into curiosity. As Klein puts it, "There will be bad things that happen, no matter what we do, and we have a choice of how we respond to them."

4. Accept that it's not about you.
"One of the tools that I find is most useful in navigating the unknown is this realization that it's not about me," explains Klein. "I get so much more strength if I'm standing up for my partners or if I'm championing an idea that's bigger than me, that's outside of me."

5. Yes, And…
Klein on the most well-known of improv principles: "People who say 'yes' are rewarded by the adventures they have. People who say 'no' are rewarded by the safety they attain. They're both good choices—safety and adventure—but you have to know which one you're choosing."

"I loved this conversation because Dan models a kind of joyful mastery that's so rare," says host Lisa Kay Solomon. "He shows how creativity isn't about control—it's about connection. His work helps us all remember that flexibility and kindness aren't soft skills—they're future-ready superpowers."

"Lisa's ability to bring out the deepest insights from her guests is a gift. This episode with Dan is a masterclass in how improvisation principles can transform not just our work, but the way we show up in the world," says Janaki Kumar, Chief Design Officer, Global Banking at JPMorgan Chase & Co.

About the Guest

Dan Klein is a lecturer at Stanford University's Graduate School of Business and Department of Theater & Performance Studies. For more than two decades, he has taught improvisation, creativity, and storytelling to students and organizations around the world. A longtime collaborator with the Stanford d.school, he is known for blending humor, humanity, and deep insight into how people learn, lead, and create together.

About the Podcast

How We Future with Lisa Kay Solomon is a weekly series about shaping tomorrow intentionally, optimistically, and strategically. Each episode features changemakers across disciplines—educators, designers, artists, scientists—who show how imagination and action can build better futures. New episodes are available on all major podcast platforms.

SOURCE How We Future Podcast