Eeke de Milliano, Geoff Charles, Shishir Mehrotra: My favorite interview questions from 100+ guests
嘉宾：Eeke de Milliano、Geoff Charles、Shishir Mehrotra、Yuhki Yamashita、Katie Dill、Karri Saarinen、Camille Hearst、Jiaona Zhang、Noah Weiss、Ben Williams、Meltem Kuran Berkowitz、Paige Costello、Nikhyl Singhal、Ayo Omojola、Scott Belsky、Lauryn Isford、Paul Adams
精读 · 按主题梳理核心观点、论证与案例。
§01Why ask for the hardest thing someone has done?
Lenny frames the episode as a collection of 17 interview questions gathered from more than a hundred guests. The aim is practical: interviewers can use the prompts to improve their own process, while candidates can use them to prepare for likely conversations.
Geoff Charles asks candidates to describe the hardest thing they have done. He wants to learn what difficulty means to each person, why the challenge was hard, and how they responded. The follow-up matters as much as the headline: he listens for how candidates worked with other people and how much agency they exercised in moving through the obstacle.
The prompt does not assume that everyone faces the same kind of hardship. Its value is in eliciting the candidate’s own definition of difficulty and a concrete account of their choices, collaboration, and effort. The excerpt offers this as a useful signal, rather than a standardized score or proof of future performance.