What kind of person should I look for when hiring for a small team that has no playbook yet?

When there's no playbook, almost everything is unknown. Who's going to buy this? How are they going to use it? What's it going to be called? Who are we going to hire? So you're not hiring someone to run a process. You're hiring someone who can reach into a tool chest and pick the right thing for the moment.

I mentioned my three filters earlier: hands-on, able to work at both the strategic top and the execution bottom, and high craft. The second one matters a lot here. If someone can't explain the big picture, they can't tell you whether pixel A or pixel B is better. "I like this one" is a useless conversation. "This one accomplishes the goal" is a useful one. I've been asking some version of can they get the big picture behind what you're doing? for over fifteen years.

A few more things I'd add for small teams specifically.

Look for curiosity across domains. The best people have poked into lots of different areas and gone deep on a problem. You can usually tell after two questions: "Why was this important?" and "What led you in this direction?" People who really understand the problem can talk clearly about what they're doing and why.

Hire your blind spots. Michael Lopp made this point years ago: your first hire needs to fill in your blind spots, and when you're small everyone needs to be able to do everything, so hire complete people who can talk about any aspect of the business.

Watch for "designing for approval." Many people from big companies have spent years trying to get sign-off from product, engineering, legal, and VPs. That habit doesn't help in a startup. AI now makes it cheap for anyone to show up with a prototype, so the key skill is separating signal from noise: deciding what matters and making sure that's what ships.

Check for comfort with ambiguity. No structure is both liberating as well as unmooring and unnerving for a lot of people who welcome some structure. Some great people do their best work inside a defined system. That's fine, but it's a different role.

And give the search real time. I truly believe finding the right people is hands down the most important thing. Ideas are cheap (a thousand other people probably had yours). The people who can make them real are not.

So when you interview, skip the "how did you get everyone aligned" stories. Ask them to walk you from "we're looking at this area" to "this is why the product should work this way." If they can do that with good taste, hire them.