My favorite interview questions from 100+ guests

1. Identify Core Decision Questions

Use a low-stakes, made-up scenario (like the ’teleportation device’ test) to assess a candidate’s ability to identify ’eigenquestions’ – the one or two core questions that unlock critical decisions and drive a plan, rather than getting lost in superficial details.

2. Gauge Self-Awareness & Curiosity

Ask candidates, ‘To what do you attribute your success and you can’t say luck?’ to reveal their self-awareness, curiosity, and reflective thinking about their journey and the world.

3. Assess Navigating Ambiguity

Ask behavioral questions about challenging or ambiguous situations to see if candidates can structure a way forward, seek inputs, and define milestones to test if their charted path is working, rather than just swimming in uncertainty.

4. Uncover Introspection & Limitations

Ask candidates about something they’ve learned about themselves that reveals a limitation in how they work, or about times things went wrong, to test their introspection, openness, and ability to reflect rather than blame.

5. Evaluate Problem Storytelling

Ask candidates to describe a big problem they worked on, looking for their ability to compellingly articulate its existential importance and rally others, demonstrating strong storytelling and communication skills essential for product roles.

6. Understand Motivations & Values

Ask candidates, ‘Tell me what work you are most proud of and why?’ to understand their taste, judgment, motivations, work ethic, values, and what ‘good’ looks like to them professionally or personally.

7. Test Authentic Opinions

Ask, ‘What’s something everyone takes for granted that you think is essentially hogwash or inaccurate?’ to break the interview mindset and elicit genuine, opinionated, and authentic thinking from candidates.

8. Reflect on Unexpected Outcomes

Ask candidates about something they did that worked out but not for the reason they thought, or a good decision that didn’t work, to gauge their introspection and ability to learn from past decisions and adapt their mental models.

9. Probe Definition of Difficulty

Ask, ‘What’s the hardest thing you’ve ever done?’ to understand a candidate’s definition of difficulty, their approach to overcoming challenges, their collaboration skills, and their agency in problem-solving.

10. Gauge Sincerity & Self-Awareness

Ask candidates, ‘What would your siblings (or parents) say about you?’ to assess their sincerity and self-awareness, looking for humble and realistic self-perception rather than a ‘bullshit answer’.

11. Assess Handling Controversy

Ask candidates to describe a time they were part of a controversial product decision to evaluate their ability to understand and represent both sides of a conflict and demonstrate even-keeled, multi-perspective thinking.

12. Uncover Unique Team Insights

Ask, ‘What unfair secrets have you learned to improve the velocity and energy level of a product team?’ to elicit unique, non-obvious bits of inspiration and practical learnings beyond conventional wisdom.

13. Evaluate Growth Mindset

Ask, ‘Fast forward three years, what’s different about you then?’ to look for signals of humility and self-awareness around areas of personal and professional growth, rather than just aspirations for role or title.

14. Observe Innate Curiosity

Throughout an interview, actively look for a candidate’s curiosity, noting if they frequently ask ‘why’ questions, as this indicates a key trait of good product managers.

15. Assess Humility & Privilege

Ask candidates, ‘Do you consider yourself lucky?’ to gauge their comfort with admitting privilege and demonstrating humility, as those comfortable with their success often acknowledge external factors.

16. Define Impact for Growth Roles

For growth practitioners, ask, ‘Tell me about a time that you delivered something that was impactful,’ to understand how they define impact and their intrinsic motivation for business outcomes.

17. Reference Call Feedback Strategy

When conducting reference calls for a candidate you intend to hire, ask, ‘What feedback will I be giving this person in their first performance review?’ to elicit honest, specific, and actionable feedback that referees cannot easily dodge.

18. Candidate Value Alignment

As a candidate, ask interviewers about their personal involvement in diversity, equity, inclusion, and belonging initiatives to test alignment of your personal values with those of the company and potential colleagues.