to be or not to be: multi-hats

I often hear this debate in startups, especially when progress starts to feel slower than expected.

Should you create focused teams with clear responsibilities, or bring in a few smart generalists who can handle different tasks as needed?

Both approaches seem reasonable at first. But in reality, trying to combine them is where things start to fall apart.

In most startups, people move between roles and teams, even if the org chart looks neat. The same person might appear in several places, which means they have to switch mindsets quickly. This is when things start to overlap. Decisions and tradeoffs from one team can affect another. Each team might work well on its own, but together, progress slows down.

This isn’t really a problem with time, meetings, or documentation. It’s a mental challenge. Every team has its own view of what matters, what can be flexible, and what “good” looks like. When someone is on several teams at once, they’re expected to change how they think based on their current role. We don’t talk about this much, but we rely on it all the time.

It’s a bit like playing games like Mafia or Werewolf. Each player has a role, and the game only works if everyone keeps their roles straight. If you start thinking like the wrong role, the game doesn’t work. Now imagine playing several of these games at once and getting penalized for mixing them up. That’s what we often expect from people in early teams.

The problem isn’t hiring generalists. Early startups actually need them. The real issue is asking people to juggle several roles at the same time, instead of letting them focus on one. People can switch roles over time, but it’s much harder to handle a few conflicting roles all at once.

We see the same thing when designing agents. Agents that try to do everything seem powerful, but they lose effectiveness if their context isn’t clear. The best agents have clear boundaries, focused tasks, and clear handoffs. You get a wide range of skills by combining specialized agents, not by expecting one to do it all.

Whether you’re talking about teams or agents, speed doesn’t come from everyone doing everything. It comes from being clear about who you are, what context you’re working in, and what you’re not responsible for right now.