Build a Running List of Interview Questions

As an entrepreneur who’s interviewed hundreds (thousands?) of people over the years for jobs, I’ve developed a set of “go to” questions that I like asking. Only, as with anything, the list has evolved over time as some become stale and new ones feel more effective. Having done it so many times, I’ve become a connoisseur of interview question and enjoy continually tweaking them.

Just recently, I heard a new one that I really like and added to the list:

How lucky are you?

I want to hear that the candidate believes some part of their success came from timing, other people helping, and/or other contributions that were lucky along the way. It’s also a form of asking if a person is humble and grateful without using those words. For these reasons, and more, I like this new interview question.

The most important interview question is related to the startup’s core values. Whatever the values, there should be one or more questions per value that pertains to it without asking about the value explicitly. With our people values of positive, self-starting, and supportive, we have a unique line of questioning that are traditional interview questions. Value-question alignment is the most important part of the interview process, even more than the subject matter competency.

Another set of questions I like is based on the chronological in-depth survey of the candidate’s past. The goal is to spend 3-4 hours with the candidate to understand their career arc and details that paint the most complete picture. Simple, superficial chats aren’t enough.

Entrepreneurs would do well to put together a Google Doc or Notion Doc with a running list of their favorite interview questions. It should be a living doc that’s visited regularly, and when a new question emerges, add it to the list and continually experiment with them. The better the interview questions, the better you understand the candidate.