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By Lenny Rachitsky · lennysnewsletter.com · @lennysan on X · YouTube · LinkedIn
Lenny Rachitsky compiles 25 high-signal interview questions gathered from roughly 150 podcast guests, grouped by theme: handling hard situations, how candidates think, how they build and drive impact, who they are as people, and unexpected prompts. The core argument is that well-chosen questions surface far more about a candidate in a short interview than generic ones do, and that good answers reveal honesty, self-awareness, and judgment.
Subscriber post — summary only01Key takeaways
- Ask about biggest failures; raw, honest accounts of what went wrong signal self-awareness and maturity.
- Probe ambiguity and hard situations to see whether candidates seek structure, inputs, and help.
- Questions that break interview scripts can reveal whether a candidate is authentic and opinionated.
- Ask what a candidate would want to change about their current job to gauge their limits and fit.
- Ask what question you should have asked them; it often produces a candid, unrehearsed answer.
“the rawer the answer in terms of how bad it was and why, the better.”Annie Pearl · Lenny’s Newsletter
“You can't say 'luck.' I always kind of want to know how self-aware are you, basically, and how curious are you.”Eeke de Milliano · Lenny’s Newsletter
02Frameworks mentioned
Summary and takeaways written by PM Atlas; quotes are short excerpts. © the original author.