Design teams are getting smaller. Every hire matters more than it did two years ago.

When I interview design candidates, I ask one question that tells me almost everything.

Show me work that failed.

Not "tell me about a challenge." Not "what would you do differently." Show me something that didn't ship, got killed, or landed wrong. Walk me through it.


Most candidates show me the failure. What I'm actually watching is how they talk about the people around it.

Do they own the outcome or distribute the blame? Do they name the stakeholder who killed it with bitterness in their voice, or do they reflect on what they learned working under that kind of pressure? Do they protect their idea or interrogate it?

That answer tells me how this person will operate inside your organization. Not how talented they are. Not how strong their portfolio is. How they will handle the moment — and there will always be a moment — when someone with more authority makes a call they disagree with.


That is what nobody tells you when you are hiring your first design leader. Portfolio is the easy part. You are not just hiring taste. You are hiring someone who has to hold a strong point of view and still move the work forward when the room does not agree with them.

The failure question finds that person every time.