Week 22, 2026—Issue #416
Learn to Play Organizational Jazz
File this under #management
There is a debate in Silicon Valley right now about how leaders should behave. Founder Mode: stay close to the work, bypass layers, maintain direct contact with what actually happens; or Manager Mode: delegate, trust the system, manage from a distance.
It is an interesting conversation, but also a narrow one. Both modes assume someone is firmly in charge. The question is only how they exercise that authority.
WorkMatters has been interested in a different question: whether organisations can be structured so that centralised, permanent authority matters less. Not leaderlessness, necessarily; someone is always in charge, and that is fine. The question is whether it always has to be the same person. Self-organising teams distribute authority to whoever is best positioned to make a given decision. Leadership becomes contextual rather than positional.
These two conversations have felt largely incompatible. Then I listened to Ivan Zhao, co-founder and CEO of Notion, on Brian Halligan’s Strange Long Trip podcast.
Most companies start small. The founder is in the room, trust is high, communication is direct. No one needs a detailed plan because everyone knows the tune. Then the company grows, layers appear, and the instinct, rational enough, is to write things down and coordinate from the top. The jazz band becomes a marching band. Everyone plays their part on cue, following a score written by someone else. Stable, but slow. Coordinated, but initiative-poor.
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Zhao calls the alternative Jazz Mode. The jazz band still has a leader: someone who sets the tune, the key, and the tempo. What it doesn’t have is a score everyone follows note for note. Within that structure, musicians listen, respond, and improvise. And that’s important, given where we’re at. With AI, every week brings something new that wasn’t possible the week before. Under those conditions, the marching band has a serious problem that the jazz band doesn’t.
To be clear, Jazz Mode is not self-organisation. But it is not Founder Mode or Manager Mode either. Those debates are about who holds authority. Jazz Mode is about how authority flows. It is maybe the most honest starting point I have come across for anyone trying to build something that doesn’t eventually collapse into a marching band.
/Andreas
Sidenotes
😎 Agency
Zhao mentions that Notion has shifted what it hires for: less experience, more agency and taste. Language models have democratised capability. Almost anyone can write and code adequately now. What they cannot replicate is judgement about what is worth building, and the will to go build it.
🌱 Refounding
If your organisation feels more like a marching band than a jazz band, the instinct might be to pivot. But a pivot changes what you do. Zhao’s word for what you actually need is a refounding: it changes who you are. He has done it twice at Notion, and each time the question was identity rather than strategy.
How can we build better organizations? That’s the question I’ve been trying to answer for the past 10 years. Each week, I share some of what I’ve learned in an email newsletter called WorkMatters. Back issues are marinated for three months before being published to Medium. This article was originally published on May 29, 2026. If you are reading this you are missing out. Subscribe to email updates at www.workmatters.studio.
