The Best Interview Questions

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Over the last 11 years, I estimate that I have interviewed more than 1,000 candidates. The candidates I interviewed in 2023 were much more interesting and impressive than the candidates I interviewed in 2013. I think I know why. I learned to ask more interesting questions. Two questions, in particular, changed my approach to interviews and my mindset about work.

I've conducted an unusual number of sales interviews since 2013. Companies hire me to improve sales performance and I believe strongly that hiring well is a powerful lever. At multiple companies, I asked to be part of the interview team for every sales hire for a period of time. I would spend up to 30 hours per week interviewing candidates (and then another 30-40 hours per week doing my real job).

For my first ~200 interviews, my process was an extremely common one: (1) Scan resume for sixty seconds and prejudge whether this candidate is qualified, (2) Judge their "presence" over the first two minutes of the interview and decide whether to recommend this candidate, (3) Fill the remaining minutes of the interview pretending to be interested. Five minutes into each interview, I would start stressing about all of the other things I should be doing.

My calendar - 30 hours per week - signaled that I believed hiring well was important. My approach and my attention suggested that I was not committed to that belief.

"Morality is mostly about how you pay attention to others." - Iris Murdoch

I chose to change my approach. If I was going to invest that much time, I should use that time to improve as an interviewer. I started experimenting with different questions and techniques.

I quickly discovered that the conversations were much more interesting if the interviewer (me) asked more interesting questions. I also discovered that my intent for the interview affected my attention span. If my intent was to find reasons to exclude a candidate, my attention span was really short. When my intent was to learn something interesting about the candidate that's not on their resume, I could stay engaged much longer.

Hundreds of interviews later, there are two questions that made my interviews more productive and also changed my mindset about my work life:

"What do you love most about the work you do now?" Candidates do not have a pre-scripted answer to this question. In fact, most haven't ever reflected on what they love about their current role, only what's missing. I love this interview prompt because it launches a conversation about the best version of that person. This question is also a powerful prompt for managing my own mindset towards my work. Reflecting on what I love most about my work is more hopeful and actionable than ruminating about what's not perfect. It's a prompt that forces you into a gratitude mindset and I think we all make better choices and better career decisions from that mindset.

"In what ways would this person make our team stronger?" Interviews became my best use of time once I started approaching them with the intent to answer this question. The wording of this question is critical. It assumes that the candidate can make our team stronger. It is up to me to uncover the unique experiences, skills and perspectives of this candidate that would complement our existing team. I learned interesting and impressive things about every candidate that I never would have discovered if I interviewed with the intent to exclude. I have applied this same principle in my everyday work life - WYLFIWYF - "What you look for is what you find!"

"I've come to think of questioning as a moral practice. When you are asking a good question, you are adopting a posture of humility." - David Brooks, How to Know a Person

I recommend two actions to do today:

• Write your answer to this question: "What do you love most about the work you do today?" Write it somewhere where you can edit it as you have new thoughts. Your best career choices will be made when you have clarity on that question. Find ways to work more of what you love most into your schedule next week.
• Order How to Know a Person by David Brooks or watch/listen to the interviews he's done as part of his book tour. I read this a couple of months ago and I have marked it up extensively with highlights and notes. I will be reading this book again and ordering extra copies for my kids and friends.

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