Notes on hiring your first designer

I have been the first designer at two companies and I have hired the first designer at one. Both experiences were harder than they needed to be, in the same way and for the same reason.

You are probably hiring for the wrong stage

Founders tend to hire the designer whose portfolio they most enjoy looking at. That portfolio is usually full of finished work: a mature product, a design system, a case study with before and after. It is genuinely beautiful. It is also evidence of a person who is good at the stage after the one you are at.

The first designer at a young company spends very little time making things beautiful. They spend it deciding what to build, arguing about scope, drawing something rough enough that six people can disagree about it productively, and then doing it again on Thursday. If you hire someone whose joy is in refinement, you will both be miserable, and neither of you will understand why.

Ask what they did in the two weeks before the screenshots in their portfolio. The answer tells you which stage they actually like.

What to look for instead

• They ask about the business. Not politely, at the end. Early, and repeatedly, because they cannot design without it.
• They show unfinished work. Someone who only shows the final frame either does not keep their sketches or does not trust you with them. Both are a problem.
• They can build something, even badly. Not because you need them to ship code, but because it changes what they propose. People who have felt the cost of an idea propose cheaper ideas.
• They disagree with you in the interview. If they do not push back once on something you said, they will not push back in month four either, and month four is when it matters.

The thing nobody tells you to prepare

The first designer will ask you what the product is for, and you need a real answer, in a sentence. Not a market, not a segment. What the person is trying to finish.

At Passe I could not answer that question for eleven days. Our first designer spent those eleven days making our existing screens marginally nicer, because it was the only useful thing available to her. That was my failure, not hers, and it is the single most expensive fortnight I have ever been responsible for.

Write the sentence before you post the job.