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Designing for AI Failure Interview Questions

What the product should do when the model returns nothing useful, how to fall back to a non-AI version instead of breaking, and how to help a user recover after an agent takes a wrong action.

  • 22 questions with model answers
  • 2 foundational · 9 intermediate · 11 advanced

Foundational Designing for AI Failure Questions

  1. What should happen in the UI when the model returns nothing usable?Case
  2. Critique an error state that says something went wrong, please try again.Artifact critique

Intermediate Designing for AI Failure Questions

  1. Design the fallback experience for an AI feature when the provider is down.Case
  2. Explain the difference between failing loudly and failing silently, and which you prefer.Concept
  3. Describe three failure modes to design for before launch.Concept
  4. What error message would you write for a model timeout, and what would you avoid saying?Artifact critique
  5. What is the right undo experience for AI-generated changes?Case
  6. Describe the escalation path from AI to human and its design requirements.Case
  7. What should a rate-limited user see, and how do you avoid making it feel punitive?Case
  8. Describe the difference between a retry that helps and a retry that just costs money.Concept
  9. What failure telemetry does design need in order to improve the experience?Concept

Advanced Designing for AI Failure Questions

  1. How do you design a feature that degrades to a non-AI version rather than breaking?Case
  2. How should the product behave when the model produces output that fails a safety filter?Case
  3. Design the recovery path for a user whose agent took a wrong action.Case
  4. Explain the concept of a blast radius for an AI feature and how design limits it.Concept
  5. How do you design for the case where the model is confidently wrong?Case
  6. Explain how to design a kill switch that product can operate without an engineer.Concept
  7. How do you preserve user work when an AI operation fails midway?Case
  8. Design the experience for a partial result rather than a failure.Case
  9. What does graceful degradation look like for a multi-step agent?Concept
  10. How would you handle a failure that only affects a subset of languages or regions?Case
  11. Walk me through the failure states you would design for a feature I name.Interview

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