Yes and… Good Improv and Strategic Leadership

Tweezer > Strategy Jam > Tweezer

Hear Me Out

I’m a crier. Saying goodbye to my old job meant a string of tearful one-on-ones and hallway hugs. To spare everyone one last tear-bath, I asked my team to roast me at the farewell party instead.

They were too kind. Mostly. The sharpest jab? “Aaron’s a Phish fan.” During the group photo the photographer skipped “Cheese” and asked, “Favorite Phish song?” I had to shout “Tweezer,” obviously.

Guilty as charged. Last weekend, fresh off Disney with the kids, I drove to Manchester for three Phish shows, my personal Magic Kingdom. And, on Sunday, to my thrill, they turned “Tweezer” into a 50-minute jam that disappeared into two other songs before snapping back to the original riff.

Now you’re probably thinking, is Aaron turning this into a Phish blog? As my kids would say, “hear me out.”

Strategy as a Groove

If Phish makes you roll your eyes (my wife feels your pain), stay with me. Their jams are a master-class in good improvisation, exactly the skill adaptive leaders need to succeed. And they’re the perfect foil to the bad improv I warned about in my last post.

Strategy is about setting the frame for intentional action. Good strategy provides a scope, a container, a groove, that is wide enough for invention but firm enough to hold together purposefully and thematically. Tweezer is built on simple loop: a modal vamp the ban can stretch, warp, even abandon, before dropping back into a rocking riff that feels like home.

The best strategies work the same way. They are adaptive and resilient, able to accommodate and incorporate disruption, absorb new information, and even seed the next strategy. Henry Mintzberg famously defined strategy “as a pattern in a stream of decisions.” He argued that effective organizations treat strategy as iterative sense-making, not architectural blueprinting. Strategy, in Mintzberg’s telling, is a creative learning process. Organizational strategies are established as emergent patterns of effective action are recognized, repeated, and refined. In this way strategy involves intention, experimentation, pattern recognition, and iteration. Just like a Phish jam!

The First Rule of Improv: Listen

Lead guitarist Trey Anastasio will tell you is that the key to Phish’s improvisational genius is a combination of intentional practice and listening. The band engages in deep active listening. They listen to each other, to the crowd, to the moment. The mindset required here is, first and foremost, curiosity. To be curious is to admit the possibility of mystery, to wonder, and to have the courage to explore.

When Peter Matthiessen went on his pilgrimage to Tibet, after his wife died, as described in The Snow Leopard, his teacher Katagiri Roshi gave him one instruction, “have no expectations.” Search for the Snow Leopard but do not expect to find it. To empty the mind of expectations is to admit the possibility of mystery. It is to be open to mystery that allows becoming, emergence, and innovation. It is to say, “What song are they playing anyway? This can’t still be Tweezer!”

Bad improvisation fails the first step of deep, active listening. The actor hears only what fits a prewritten script, dismisses the offer, and plows ahead.

Yes And

Good improvisation begins by listening. But then we must act. It is improvisation after all. This is where the core improvisational teaching of “Yes and” comes in.

“Yes and” requires us to acknowledge the contribution of others and accept the reality we are cocreating (yes), add a new possibility, and invite the next person to build (and). A good “yes-and” expands freedom; a “no-but” shuts the scene down.

Saying “Yes and” requires courage. Leaving a song’s scaffold behind is risky. No one knows where this is going. The jam could fall apart. Indeed, sometimes it does and chaos ensues. There is an element of chaos to any act of creation. To allow new forms to emerge we need to accept the chaos of the liminal, the in between, the song before, the jam in between, and the new structure yet to form. We need to take risks! In my experience, few leaders have tolerance for this phase, the messy middle, but this is where we learn and innovate. From chaos novel forms emerge.

Role Flexibility: Serve the Scene

Unlike scripted actors, improvisers swap roles fluidly, following the needs of the scene. In my experience role fluidity is an underappreciated aspect of strong teams. It boosts resilience, cross-pollinates skills, and softens hierarchy. Psychological safety rises because status is temporary and purpose is shared.

Servant leadership, first articulated by Robert Greenleaf, is role fluidity in action. The leader serves the team—clearing blockers, asking clarifying questions, sharing spotlight. Purpose over position, just as an improviser adopts whatever role moves the jam forward.

To sum up, Phish is good actually, and strategic leaders do some of the same things Phish does. They set a flexible strategic framework, tune in without pre-scripted answers, build on every contribution, tolerate the messy middle, and serve the team. Good leadership starts with presence, allows experimentation, always returning to purpose.