My favorite interview questions from 100+ guests
This episode compiles 17 favorite interview questions from over 100 podcast guests, offering high-value insights for both interviewers to improve their process and candidates to prepare for diverse questions.
Deep Dive Analysis
16 Topic Outline
Introduction to Favorite Interview Questions Compilation
Eka Demeliano's Question: Attributing Success
Jeff Charles's Question: Overcoming Hardship
Shishir Mehrotra's Coda Eigenquestion Test
Yuhki Yamashita's Questions: Controversial Decisions & Big Problems
Katie Dill, Kari Saarinen, Camille Hurst's Shared Question: Most Proud Work
Jiaona Zhang's Question: Navigating Ambiguity
Noah Weiss's Question: Unfair Secrets for Team Velocity
Ben Williams's Question: Future Self-Growth & Curiosity
Meltem Kuran Berkowitz's Question: Sibling/Parent Perspective
Paige Costello's Question: When Things Went Wrong
Nikhyl Singhal's Question: Challenging Conventional Wisdom
Ayo Omojola's Question: Unintended Outcomes & Failed Good Decisions
Scott Belsky's Questions: Personal Limitations & Luck
Lauryn Isford's Question: Defining Impact
Paul Adams's Reference Call Advice
3 Key Concepts
Eigenquestion Test
This framework, introduced by Shishir Mehrotra, involves identifying the one or two critical questions that, once answered, unlock the core understanding or strategic plan for a complex problem. It tests a candidate's ability to simplify complex situations and focus on high-leverage information.
Navigating Ambiguity
Described by Jiaona Zhang as a key skill for Product Managers, it involves the ability to create structure and a path forward in unclear situations. This includes seeking inputs, being open to changing direction, and setting small milestones to test if a chosen path is working.
Introspection
Highlighted by Ayo Omojola and Scott Belsky, introspection in candidates refers to their capacity for self-reflection. It's about understanding why decisions worked or didn't, acknowledging personal limitations, and being open about struggles rather than blaming external factors.
15 Questions Answered
She asks, 'To what do you attribute your success and you can't say luck?' to assess a candidate's self-awareness and curiosity about their own journey.
He asks, 'What's the hardest thing you've ever done?' to understand a candidate's definition of difficulty, how they overcome challenges, and their agency in problem-solving.
He uses a 'teleportation device' scenario, asking candidates to identify the two most critical questions they would ask scientists before developing a market plan, to test their ability to find 'eigenquestions'.
He asks candidates to describe a time they were part of a controversial product decision, looking for their ability to represent different perspectives, and also asks about a big problem they worked on to assess storytelling and communication skills.
They all ask, 'Tell me what work you are most proud of,' to understand a candidate's taste, judgment, motivations, and what they consider a successful outcome.
She asks behavioral questions about challenging or ambiguous situations to see how candidates navigate uncertainty by creating structure, seeking inputs, and setting milestones to test their path forward.
He asks, 'What unfair secrets have you learned to improve the velocity and energy level of a product team?' to uncover unique insights and inspiration beyond conventional wisdom.
He asks, 'Fast forward three years, what's different about you then?' to look for signals of humility and self-awareness regarding personal and professional growth areas.
She asks, 'What would your siblings say about you?' (or parents if no siblings) to gauge a candidate's sincerity and self-awareness about how others perceive them.
She asks, 'Tell me about a time something went wrong,' to evaluate a candidate's mindset, introspection, and how they perceive themselves and the situation when things are not working well.
He asks, 'What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?' to break the typical interview mindset and test for genuine, opinionated authenticity.
He asks, 'Tell me something you did that worked out, but not for the reason that you thought it would work,' or 'Tell me something you did that was a good decision that didn't work,' to assess a candidate's introspection and ability to learn from past experiences.
He asks about something people have learned about themselves that reveals a limitation in how they work, to test introspection and openness, and also asks, 'Do you consider yourself lucky?' to gauge humility and perspective.
She asks, 'Tell me about a time that you delivered something that was impactful,' to understand how candidates define impact and their intrinsic motivation for achieving it.
He suggests asking, 'What feedback will I be giving this person in their first performance review?' to elicit honest and enlightening feedback that referees cannot easily dodge.
18 Actionable Insights
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.
7 Key Quotes
To what do you attribute your success and you can't say luck?
Eka Demeliano
What unfair secrets have you learned to improve the velocity and energy level of a product team?
Noah Weiss
Fast forward three years, what's different about you then?
Ben Williams
What would your siblings say about you?
Meltem Kuran Berkowitz
What's something that everyone takes for granted that you think is essentially hogwash or inaccurate?
Nikhyl Singhal
Tell me something you did that worked out, but not for the reason that you thought it would work. Or tell me something you did that was a good decision that didn't work.
Ayo Omojola
What feedback will I be giving this person in their first performance review?
Paul Adams
2 Protocols
Shishir Mehrotra's Coda Eigenquestion Test
Shishir Mehrotra- Present a hypothetical, complex scenario (e.g., a teleportation device) and ask the candidate how they would bring it to market.
- Allow the candidate to ask initial clarifying questions.
- Inform the candidate that the 'scientists' will only answer two of their questions.
- Ask the candidate: 'What two questions do you ask?'
- Evaluate the candidate's ability to identify the most critical, high-leverage questions that would unlock a strategic plan, rather than superficial details.
Paul Adams's Killer Reference Call Question
Paul Adams- When conducting a reference call for a candidate you intend to hire, ask the referee: 'What feedback will I be giving this person in their first performance review?'
- Use the referee's answer to gain honest and specific insights into the candidate's potential areas for growth or improvement.