Top Interview Questions from UX Industry Leaders

Explore top interview questions from UX experts. Essential insights for interviewers and candidates alike in this concise guide

Top Interview Questions from UX Industry Leaders


The job interview process can be daunting, both for interviewers seeking the right questions to uncover the best candidates and for interviewees preparing to showcase their skills and personality. Lenny Rachitsky, the host of a popular podcast, has compiled a remarkable collection of interview questions from over a hundred guests. This article quickly sums up the most insightful interview questions shared by industry experts, providing valuable perspectives for both sides of the interview table.

Check out Lenny's Episode here:

Key Interview Questions and Insights

1. Eeke De Miliano (Retool & Stripe) - Question: "To what do you attribute your success, excluding luck?"

  • Insight: This question assesses self-awareness and reflection, looking beyond humility to understand a candidate's true drivers of success.

2. Geoff Charles (Ramp) - Question: "What's the hardest thing you've ever done?"

  • Insight: Understanding a candidate's definition of difficulty and their approach to overcoming challenges reveals resilience and problem-solving skills.

3. Shishir Mehrotra (Coda) - Question: "How would you market a hypothetical teleportation device?"

  • Insight: This imaginative scenario tests strategic thinking and the ability to ask critical, defining questions.

4. Yuhki Yamashita (Figma & Uber) - Question: "Describe a controversial product decision you were part of."

  • Insight: This question uncovers a candidate's ability to understand and navigate complex, conflict-laden situations.

5. Katie Dill, Karri Saarinen, Camille Hearst - Question: "Tell me what work you are most proud of?"

Insight: This question reveals a candidate's taste, judgment, motivation, and what they consider high-quality work.

6. Jiaona Zhang (Webflow & Airbnb) - Question: "Share your experience navigating ambiguity."

  • Insight: The response highlights how a candidate structures their approach and seeks help in uncertain situations, a key trait for roles like Product Management where ambiguity is common.

7. Noah Weiss (Slack) - Question: "What unfair secrets have you learned to improve the velocity and energy level of a product team?"

  • Insight: This question seeks to uncover unique, effective strategies a candidate has discovered, offering a glimpse into their innovative thinking.

8. Ben Williams (ex - Snyk) - Question: "Fast forward three years, what's different about you then?"

  • Insight: This probes for humility, self-awareness, and areas of personal and professional growth, highlighting a candidate's future aspirations and introspection.

9. Meltem Kuran Berkowitz (Deel) - Question: "What would your siblings or parents say about you?"

  • Insight: This question aims to uncover sincerity and self-awareness, providing insights into how candidates perceive themselves through others' eyes.

10. Paige Costello (Asana) - Question: "Tell me about a time something went wrong."

  • Insight: Responses to this question reveal how candidates handle failure, their mindset, and their problem-solving approaches in challenging situations.

11. Nikhyl Singhal (Facebook) - Question: "What's something everyone takes for granted that you think is hogwash?"

  • Insight: This question tests authenticity and encourages candidates to share genuine, opinionated insights, breaking away from typical interview responses.

12. Ayo Omojola (Carbon Health) - Question: "Tell me about a good decision that didn't work or one that worked for unexpected reasons."

  • Insight: This explores a candidate's introspection and ability to reflect on and learn from their decisions.

13. Scott Belsky (Adobe) - Question: "Do you consider yourself lucky?"

  • Insight: This question uncovers a candidate's perspective on luck, privilege, and their security in their achievements.

14. Lauryn Isford (Notion) - Question: "Tell me about a time you delivered something impactful."

  • Insight: This question gauges how candidates define impact and what motivates them, particularly relevant for roles in growth and product development.

15. Paul Adams (Intercom) - "What feedback will I be giving this person in their first performance review?"

  • Insight: This question for referees cuts through generic praise to reveal potential areas of improvement and growth for the candidate, providing a more balanced view.

Not included in Lenny's interview but we figured we would add one in:

16. Adam Perlis (Academy) - "If you were not working in this field, what else would you be doing?"

  • Insight: The response to this question reveals a lot about a candidate's underlying passions and interests. Understanding what excites and motivates someone beyond their current professional role can provide valuable insights into their personality, drive, and potential areas of growth. This knowledge can be leveraged by a leader to align the individual's role and responsibilities with their deeper interests, potentially increasing job satisfaction and productivity. It's a question that underscores the importance of aligning personal and professional growth, showing a company's commitment to supporting its employees' holistic development.


These interview questions, curated by Lenny from his podcast, offer a diverse range of perspectives and strategies for both interviewers and interviewees. For interviewers, they provide a toolkit to deeply understand a candidate's thought process, values, and problem-solving abilities. For those preparing for interviews, understanding the rationale behind these questions can help in crafting thoughtful, reflective answers that highlight their strengths and fit for the role.

Whether you are on the lookout for new talent or preparing to make your next career move, these insights from industry leaders can serve as a valuable guide in the art of interviewing.