The Failure Interview Question
Ask senior candidates about one time they failed and what they learned — and watch how they answer.
- Difficulty
- Easy
- Time to result
- ~days to results
- Steps
- 3
- Confidence
- 82%
A single high-signal interview question for evaluating senior hires: ask about one specific time they failed and what they learned from it. The value is in the failure modes it exposes — candidates who claim they've never failed, or who reframe a success as a failure, reveal either self-awareness gaps or shallow experience. The interviewer's job is to hold out for a real, solid, specific example.
Origin
Shweta Shrivastava's favorite interview question, used especially at senior levels across her career as a hiring product leader.
Core principles
- 01A genuine failure story requires both self-awareness and real depth of experience
- 02Claiming to have never failed is itself a red flag
- 03Reframing a success as a failure signals lack of self-awareness or shallow experience
- 04Push for a real, solid, specific example rather than accepting a generic answer
How to run it
- 1
Ask the question, especially at senior levels
Ask the candidate: what was one time that you failed, and what did you learn from it? Reserve special weight for this at senior levels.
Pro tip Frame it as one specific instance, not 'a weakness' — you want a concrete story, not a rehearsed platitude.
- 2
Read the failure modes in the answer
Note candidates who say they've never failed, or who dress up a success story as a failure — these usually indicate a self-awareness gap or insufficient depth of experience.
Watch out A polished 'my biggest failure was working too hard' style answer is the success-as-failure tell; treat it as a miss, not a strength.
- 3
Hold out for a solid example
Keep probing until you get a real, specific failure with a genuine lesson; that is the signal you're looking for.
Pro tip The learning is as important as the failure — a real answer names what changed afterward.
In the wild
Shweta says she has seen candidates either claim they've never failed or try to pass a success story off as a failure story — both of which usually mean they lack self-awareness or haven't had the depth of experience. She asks the question specifically to surface a real, solid example.
→ The question reliably separates candidates with genuine self-awareness and depth from those without, informing senior hiring decisions.
Common mistakes
Accepting a success dressed as a failure
Letting a candidate reframe an accomplishment as their 'failure' lets a self-awareness gap slip through; Shweta treats this as a signal the person lacks depth of experience, not as a clever answer.
Not probing for a specific example
Accepting a vague or generic response defeats the purpose — the whole value is in the real, solid, specific failure and the concrete lesson drawn from it.
Is it for you?
Best for
Hiring managers and interviewers evaluating senior candidates where self-awareness and depth of experience matter more than raw skill.
Not ideal for
Junior or entry-level interviews where limited professional history makes a deep failure story an unfair or low-signal ask.
From the transcript
“I always ask them when it was one time that you failed and what did you learn from it”
“I've seen that a full tour you know was either say that they've never failed or they're trying to two guys a success story as…”
“I asked that question and I'm looking for some real solid examples there”
From the episode
Product lessons from Waymo
Shweta Shrivastava (Waymo, Amazon, Cisco)