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Name a product decision you think is bad. Now tell me why the team that made it might have been right.

5 min readUpdated 2026-08-15Target archetype: Big Tech, Enterprise Captive, Product Startup

Answer

Short answer

Separate what the design costs users from what you personally dislike, then reconstruct the constraint that produced it: a business model, an organisational boundary, a regulatory rule or a migration nobody can finish.

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Likely follow-ups

  • Which of your two explanations would you test first, and how, in a week?
  • The constraint you identified is a business-model constraint. What would have to change for the design to change?
  • How would you make this argument to the team that shipped it without them dismissing you?
  • Name a design you find ugly that you believe is correct. Why?

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