Background Deep-Dive Interview

1-1.5 hrs interview, 30m-1hr Q&A The goal is to go through past experience to determine ability and alignment of our position (scorecard).

It’s a one-on-one chronological walk-through of a person’s career. You begin by asking about the highs and lows of a person’s educational experience to gain insight into his or her background. Then you ask five simple questions, for each job in the past fifteen years, beginning with the earliest and working your way forward to the present day.

Interview Questions Framework

  1. What were you hired to do? How was your success measured? Look for: What were their mission and key outcomes? What competencies might have mattered?
  2. What accomplishments are you most proud of? Look for: Outcomes that match mission above.
  3. What were some low points during the job? What went really wrong? What was your biggest mistake? What would you have done differently? What part of the job did you not like? In what ways were your peers stronger than you? Look for: Look for understanding of areas for growth, identify environments not meant for them.
  4. What would your boss say were your strengths and areas for improvement? Use to compare against during reference checks.
  5. Why did you leave? How did your boss react? Look for: Stories of progressing career (hitting ceilings, trying new domains), philosophical differences between bosses, getting fired, their boss was disappointed about the news


The key is to dig deeper on their answers. Approach it similar to the 5 Whys framework. Tangents are a good thing. Find parts of their stories that don’t add up. Try to get specifics.

An Example

  1. Why is it your proudest accomplishment?
  2. How do you make it happen?
  3. What were the biggest obstacles?
  4. Why did you struggle with the engineers?
  5. Would you do anything differently to remove the friction?

Product Designer

Compentencies Evaluated

Questions to Ask

Product Designer Interview Questions

Compentencies Assessment

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