I've been on both sides of design leadership interviews—candidate and hiring manager.
The questions sound simple. They're not.
The Question Behind the Question
Every interview question tests one of five things:
- Can you lead without authority?
- Can you navigate organizational complexity?
- Can you translate design value?
- Can you build and develop a team?
- Do you have a point of view?
Figure out which one—then answer that.
Common Questions Decoded
"Tell me about a time you disagreed with a stakeholder."
Really asking: Can you influence people who don't report to you?
Wrong answer: A story where you were right, they were wrong, and you eventually won.
Right answer: Show you understood their perspective, found common ground, reached a better outcome together.
"How do you measure design success?"
Really asking: Can you translate design value?
Wrong answer: "User satisfaction and NPS."
Right answer: A framework connecting design to business outcomes, with specific examples.
"Tell me about a project that failed."
Really asking: Do you have self-awareness?
Wrong answer: A failure that was everyone else's fault.
Right answer: Honest ownership of your contribution, specific lessons, evidence you've applied them since.
Questions to Ask Them
- "What does success look like at 6 months? At 18 months?"
- "Who are the key stakeholders I'd need relationships with?"
- "What's the biggest challenge the design team faces?"
- "Why did the previous person leave?"
Bad questions: Anything you could find on their website.
Red Flags
- No design leaders in the interview loop
- Vague answers about design's influence
- Every question about execution speed, none about strategy
- "We want to transform design culture in 6 months"
They're evaluating you. You're evaluating whether you can succeed there.
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