My favorite interview questions from 100+ guests

Lenny Rachitsky reflects on interviews with over 100 guests from product, growth, and leadership fields, distilling his favorite questions that reliably surface candidates' self-awareness, problem-solving, and cultural fit. These questions, drawn directly from guest recommendations, emphasize behavioral examples over hypotheticals to predict real-world performance, with psychology rooted in revealing blind spots and decision-making patterns.

Self-Awareness and Growth Mindset

Several guests favored questions like "Tell me about the last time you changed your mind" or "Give me an example of when you were wrong and what you learned." These probe humility and adaptability, as people who can admit errors demonstrate psychological safety and learning agility. Rachitsky notes they work best when follow-ups dig into the emotional response, uncovering if candidates externalize blame or own outcomes.

Problem-Solving Under Pressure

Questions such as "Describe a situation where you had incomplete information but had to decide anyway" or "Walk me through a high-stakes trade-off you made" highlight analytical depth. Guests explained the psychology: pressure reveals priorities and heuristics, distinguishing rote executors from strategic thinkers. Rachitsky stresses using real examples to avoid rehearsed answers, effective for product and growth roles where ambiguity is constant.