The trumpet cuts through the room with confidence, maybe even a tinge of arrogance. The bass challenges with low and deliberate notes, pushing against the trumpet’s swagger. The drums lag just a hair behind, teasing the time signature until your sense of rhythm starts to wobble. Then the piano drops a few chords, and suddenly the whole thing comes alive.

Every musician was testing their boundaries, listening harder than they played, and trusting that the others will catch them when they leapt.

Real collaboration is a dynamic balance of confidence and surrender, of push and pull. And it’s funny, as I sat there in that small club, I couldn’t help thinking how rare that kind of interplay has become in our modern working lives. Most of our AI tools seem allergic to tension because they are trained to be perfectly agreeable.

Silicon Valley loves to mythologize collaboration, usually through a story that involves pizza, a garage, and someone sleeping under a desk. My favorite is the one about the creative team at Pixar. Creatives and executives from different projects would meet to review and break down each other's work. They called it the Braintrust. The rule was simple: brutal honesty in service of the work, never the ego. This also reminds me of Sheryl Sandberg's approach of caring personally about her employees while challenging them directly.

Lately I've been using LLMs a lot for brainstorming, planning, debating, pondering. And don't get me wrong, they have helped me think in directions I hadn't previously explored but I miss teammates who could say, “That idea’s boring, try this” or “Wait, what if we go here instead?” The soul of collaboration lives in the creative disobedience, imperfection, and exploration. Now, I’m not suggesting we want AI that argues for argument’s sake but imagine an AI that played back, not just played along.

If you ever get the chance, listen to Miles Davis’s So What (to be honest you should listen to the entire Kind of Blue album). In the first minute you sense the hesitation of piano chords probing for footing and the bass testing the floor. Then the horns join, and suddenly the band is talking.

That’s how I imagine the next generation of intelligent tools will feel like. They'll make you feel like you are a part of a jazz jam session.