“I’m not sure if I like what I did here or not”

Hearing something special from a designer I recently interviewed

Before we make the final call on hiring a designer, we always give them a sample one-week project to do for us (we pay them $1500 for the one-week exercise).

These quick one-week projects are the best way we’ve found to get inside their head — to know what they’re really capable of independently. The brief is broad and based on a real pain point that we haven’t solved yet.

A recent example was “Let’s say a Basecamp customer started out with a single project and put everything they were working on in that one project. But a few months in they realized that they should have created multiple, focused projects instead of one mega project. Design a UI that would help them tease apart their one mega project and break it into logical smaller projects.”

They then have a week to make something. It’s just the design side so it doesn’t have to work, but the closer it is to simulating how it would actually work the better.

We’re not looking for perfect — we know it’s only a week, and most people have day jobs so that week is typically only a few extra hours a night. What we’re looking for is clear thinking, solid design skills, and a mature, convincing presentation of their work. And, when we review their project with them, a calm, open-to-feedback demeanor that says “we’d love working with this person.”

Fast forward to last week.

I’ve been talking with a designer about joining our team. She’d be the first designer we’ve ever hired who was entirely focused on mobile design. Up until now, all our designers were web designers first, and sometimes mobile designers second. She’d be joining our nascent iOS team as designer number two.

She did a project for us. It wasn’t the one I described above, but something else related to capturing meetings with Basecamp. As we reviewed her work together, she said something that really impressed me.

She said “I’m not sure if I like what I did here or not”. I loved it. Not what she did, but that she said that.

It takes real confidence and self-awareness to talk to someone who’s considering hiring you and telling them that you aren’t sure you like what you did. We dug into it. It wasn’t the idea at large — she was very happy with that — it was a specific flow, a specific part of the design. She did it, but she wasn’t thrilled with it.

That’s how I feel about a lot of my work too. Especially in the early phases. I designed something, or I wrote something, but I’m not sure I really like it yet. While it’s easy to tell yourself that, it’s hard to tell someone else that — especially if they’re evaluating your work.

I’ve interviewed many designers. This level of self-awareness — especially in someone relatively junior — is rare. Most people are concerned with making themselves look the best they possibly can. They’ll defend a position with BS even when you can tell they don’t believe it.

In this case I love that she was just being honest. It made me think “I could work with her”. And in the end, isn’t that what applying for a job is all about? Making someone want to work with you?

Well done. This morning I sent her an offer. She accepted. We’re thrilled.

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