Every founder I talk to underestimates the first ten hires. Not because they don’t take hiring seriously — they take it more seriously than almost anything else — but because they think of those hires as filling roles. Engineer #2. First designer. First salesperson. The framing is wrong.

Your first ten hires aren’t roles. They’re the template. Everyone you hire after them is, consciously or not, measured against them. The bar they set becomes the bar. The way they work becomes how the company works. The things they tolerate become the things the company tolerates.

What the first ten actually do

By the time you’re at thirty people, you cannot personally interview every candidate. You cannot personally onboard every hire. You cannot personally model what “good” looks like in every function. Your first ten people start doing all of that for you — long before anyone uses the word “manager.”

This is why hiring on raw competence alone falls apart. A staff engineer who’s brilliant but treats junior teammates with quiet contempt will, by month six, have shaped how three other engineers behave. A first salesperson who closes deals by overpromising will, by month nine, have trained the next two hires to overpromise. You’re not just hiring a person. You’re hiring a propagation pattern.

What I look for now

After getting this wrong twice, I narrowed my filter to three things, in this order:

1. Do they make the people around them better? Not in a vague “good culture fit” sense. Concretely: in the interview process, did the people who debriefed with them leave the room sharper than they entered it? Did they ask questions that exposed real thinking? This is testable. Most founders don’t test for it.
2. Can they hold ambiguity without flinching? Early-stage work is a string of half-defined problems with no obvious owner. Hires who need a clean spec will spend their first six months in quiet frustration. Hires who can sit in the mess and start narrowing it become force multipliers immediately.
3. Will they tell me I’m wrong? Not theoretically — actually. The first ten hires are the people who shape what the founder believes about the company. If they default to deference, the founder’s blind spots become the company’s blind spots. I’d rather hire someone slightly less talented who will push back than someone brilliant who won’t.

The mistake I keep seeing

Founders hire for the company they have, not the company they’re about to be. You don’t need a “Director of” anything at ten people. You need ten people who can each do the work of three, who raise the bar for whoever comes next, and who you’d trust to interview your eleventh hire without you in the room.

If you can’t say yes to that last test for someone on your team today, you already know what to do.

This is the kind of question I write about every Sunday. If you found this useful, the newsletter is below — one essay a week, no upsells.

John Baugh