<aside> <img src="/icons/info-alternate_gray.svg" alt="/icons/info-alternate_gray.svg" width="40px" /> First shared June 10, 2025 | Last updated June 10, 2025

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Questions about my job is a series where I answer… questions… about my job. This particular question is one I’ve asked myself a lot over the past decade.

The short answer to this question is… IDK. It’s going to depend on what you, the person ostensibly asking this question, value in a leader. Since you’re ostensibly asking, I’m ostensibly answering. I have some ideas based on leaders I have worked with in my career!

Disclaimer

I don’t know or care about all the existing systems for, like, leadership taxonomy and personality coding.

I think archetypes and matrices and the like are largely harmless, as long as they aren’t being taken too seriously, and can even be helpful. Sometimes they work well for people seeking introspection, or a standardizable approach to the multifarious challenges of working in a group of humans. Horoscopes are good fun, and they give you something to talk about on a first date.

I’m not trying to design my own, nor do I advocate for wholesale adherence to a worldview that puts people into boxes.

How to know what you’re looking for in a design leader

Interviews are as much an assessment of a prospective employer’s leadership and organization as they are an assessment of an employee’s skillset and attitude. If you want to know who you’re signing up to work with, hit ‘em with the open-ended questions and know what answers you’re willing to accept.

Prepare a short list of priorities that you need to get answers on. No more than three, I think. It’s probably also a good activity to

How to interview a design leader

When it comes to a leader who has some kind of sway over my work life, I want to know a few high-level things before I sign up to work with them for a handful of years. These are mine:

1. How do they run their house?
2. Are ethics practical or theoretical to them?
3. Can I trust my career in their hands?

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Word to the wise:

There’s a chance you could get yourself in hot (awkward) water with some of these. If you FA, please be prepared to FO. In my opinion, it’s worth it, but you may not feel the same.

I’ve marked the more contentious questions with a 🌶️.

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Sample questions: How do they run their house?

Sample questions: Are ethics practical or theoretical to them?

Sample questions: Can I trust my career in their hands?

How to listen to what a design leader tells you