Built by Our Improvisations

In 1932, a comedian named Dudley Riggs was dying on stage in a vaudeville house, buried under boos, when his troupe did something that would later get a name: they turned to the hostile crowd and asked what they wanted to see instead. Then they built it, live, from nothing. It worked. Improv, as a discipline, was born partly out of that kind of necessity — not a taste for chaos, but a response to the fact that the room doesn’t always cooperate with the script.

I think about that story whenever a client tells me they’re waiting to feel ready before making a move that circumstances have already forced. There is rarely a script for the moment that matters most. The real skill is not the absence of preparation. It’s what you’ve built before the moment arrives that lets you respond to it without one.

A surgeon doesn’t improvise from nothing. She improvises from ten thousand hours of knowing what a body can do, so that when it does something the textbook didn’t predict, her hands already have somewhere to go. A jazz musician trading solos with a bandmate isn’t inventing from a blank page; researchers studying musicians’ brains during improvisation found that a specific region, the dorsolateral prefrontal cortex — the seat of the inner critic, the part that edits before you’ve finished the thought — goes quiet during genuine improvisation, while a different region, tied to spontaneous, embodied expression, lights up instead. The skill isn’t a lack of structure. It’s structure so well-learned that the part of you built to second-guess it can finally stand down.

I’d extend that to leadership, because I don’t think there’s a version of running anything worth running that doesn’t eventually require someone to make a real decision without a precedent to hide behind.

What I ask clients to build, when they’re heading toward one of those moments, isn’t a plan for every branch of the tree. It’s the muscle — the experience, rehearsed enough times in low-stakes rooms, that they can trust when the stakes are real. And alongside it, something harder to train directly: the willingness to let the inner critic go quiet long enough to actually respond to what’s in front of them, instead of what they’d prepared to see.

None of this is an argument for showing up without preparation and calling it faith. The philosopher Stephen Asma is right to warn about the leader who “leaps tragically into delicate situations with no plans, practice, tact, or ability to read the room.” Improvisation done well is the opposite of that — it’s the visible tip of a great deal of unglamorous rehearsal. What shows up in the room is only ever the last few seconds of a much longer preparation nobody in the audience can see.