Business Is Just Jazz with Deadlines

There’s a moment during Herbie Hancock’s Cantaloupe Island performance at a festival in Japan back in 1991 that I can’t stop thinking about.

Omar Hakim is behind the drums (check it out at about 8:30), watching intently as Herbie launches into a piano solo that’s—well, ridiculous. Not ridiculous like sloppy or chaotic. Ridiculous like, “Wait, did he just play that?” You can see the surprise and awe on Hakim’s face. He knew the tune. He knew the structure. Still, even he didn’t know what was coming next.

That’s the magic. They weren’t following a script—they were building something together in real time. No PowerPoint. No meeting notes. Just deep listening, shared rhythm, and years of context encoded in trust.

We talk about collaboration all the time in business. Most of the time what we really mean is coordination. Alignment. Project plans. All good things.

So, what happens when the plan breaks?

Improvisation Is Uncertainty with Context

I spent years in IT support. The desktop support stuff was transactional—reset a password, swap out a mouse. When something more complex happened, like the servers or network going down? That was jazz.

You never knew if it would take 10 minutes or 10 hours to get things back up and running. You didn’t know if it was a failed disk, a bad config, or a rogue update. You just jumped in. Like a fireman sliding down the pole. You just… started playing.

Improvisation isn’t chaos. It’s structured freedom.

You know the key. You know the time signature. You’re listening to everyone else. And you’re adding your own voice without derailing the whole thing.

It’s real-time collaboration. Individual creativity. Group storytelling.

The Sheet Music Is the Narrative

In music, the song gives you the framework to riff.

In business, that framework is your corporate narrative.

It’s the sheet music—the part everyone learns, internalizes, and builds from. It gives everyone common context. Yes it gives you notes you play, but it gives you a shared structure when some improvisation is called for.

I’ve written before—in The Flip Side of Delegation—about how ownership is where clarity becomes action. Improvisation is what happens when people own the outcome but still play within the theme. It’s the space between “follow this plan” and “figure it out”—and great leaders create that space on purpose.

It’s what I call Conducting the Orchestra. You’re not controlling every note. You’re setting the tempo. Giving the soloists room. Guiding the emotional arc.

That’s leadership.

When the Plan Breaks, the Band Plays On

Last week, I watched my daughter Olivia perform in the pit for a new musical she’d written. Her sister Amanda had already staged the show beautifully. Olivia was also the musical director and had pulled together a talented pit band composed of a bass player and percussionist, with her on guitar. Everything was mapped out, rehearsed, and dialed in.

Right before curtain, she realized the battery in her guitar was dead. So there would be no amplification of anything she played. Her strummed chords would still work, but the subtle finger-picking would be lost.

No panic. No meltdown. Just improv.

She adjusted. The talented band around her followed along. The show didn’t fall apart—it evolved. Because the team wasn’t just executing a plan. They understood the structure. And they trusted each other to play.

That’s what great teams do.

Listening Is the Hidden Skill

Here’s the thing: most companies don’t know how to listen.

I’ve said this before in past issues. Too often, we listen to confirm. Or worse, to reply. But not to understand.

You can’t improvise well if you’re not listening well. Improvisation only works when everyone’s tuned in. To the customer. To the market. To each other.

In jazz, you don’t listen to take your turn—you listen to add. You build. You say, “yes, and...” That’s what Herbie and Omar were doing. They weren’t trying to outplay each other. They were deepening the groove.

Improvisation Lives at the Edges

Improvisation shows up everywhere:

• A sales rep navigating a live pitch

• A support team dealing with an angry customer

• A social media manager responding to breaking news

• A founder adjusting their roadmap

• An analyst relations lead reading the room mid-briefing

That’s not winging it. That’s improvisation done right.

It’s not about abandoning strategy. It’s how strategy survives contact with reality.

I wrote about this in Never mind. I’ll Just Do It: when delegation fails and narrative clarity breaks down, plans fall apart. Improvisation is what fills the gap—when people take ownership at the edges.

My Role? Conducting the Orchestra

I’ve always loved music. As a kid, I played clarinet, saxophone, and flute in school. Picked up a little piano and guitar along the way. I even tried writing music. Some of it worked. Most of it didn’t.

But what stuck with me wasn’t performing—it was listening. Especially to jazz.

I loved hearing how complexity came together. How a group of individuals could improvise and still sound like one voice. And most of all, how the best part of jazz is live performance—where anything can happen, and everyone’s tuned in.

Over time, I’ve realized my role isn’t in the band or in the composer’s room. It’s with the conductor. I love finding the essence of what needs to be expressed—then helping the players make magic out of it.

That’s how I work with founders and teams. I help define the core narrative—then help others riff on it without losing the beat. Because great narratives aren’t fragile. They’re not stuck on the page. They’re flexible. Durable. Designed to be played live.

Berkson's Bits

Plus ça change…Vibe Coding

“Vibe coding” isn’t really coding. It’s compression. Disintermediation. A way to skip steps, collapse roles, and move fast.

We’ve seen the loop before: Mainframes → LANs → SaaS → Back to the edge.

Decentralization brings speed. But also silos. More freedom, less control. More vibes, more risk.

It’s not good or bad. Just… familiar. 

Same cycle. Different UI.

What I’m Watching...

In keeping with the jazz theme and my love for Tiny Desk concerts, here's Stanley Clarke (who was also in that version of Cantaloupe Island at the jazz festival in Japan). I love when he plays the upright bass.

If you’re a leader, improvisation isn’t optional. It’s inevitable. And the better your foundation - the clearer your narrative, the stronger your culture of trust - the better your people will sound when it’s their turn to solo.

So go ahead. Hand them the sheet music.

And then let them play.

P.S. I wrote more about this a while back in a blog post called: Improvisation: We’re All Social Jazz Musicians

Still rings true.

Looking forward to continuing the conversation...

Alan