15 People on the Most Important Question They've Ever Been Asked

“Which of my current views would I disagree with if I were born in a different country or generation?”

As someone who asks people questions for a living, I’m always interested in delving deeper into the art of the interview. I’ve studied my favorite interviewers down to their posture, their hand gestures, and their listening style. It’s not only about the questions they ask, but it’s about how they ask them.

In 2021, someone asked me for my thoughts on “how to ask great questions.” Here’s what I told them about how I approach interviews.

1) Preparation is key: I try to consume everything that the person has done in media before the interview, so I can ask questions they hopefully haven't encountered before. Spend a day trying to read, watch, and listen to every interview the person has done. You'll start noticing how they probably get asked the same questions over and over again. During the interview, try to avoid all the obvious questions and get right into the meat of it — their mindset, philosophy, the nitty gritty of their process. The point here is to make them think.

2) Engage in active listening: Most people come prepared with a list of questions they want to go through, and they miss out on being in the moment. By *actually* listening to their answers, you get to ask follow up questions. And I looooove follow up questions because that's where I believe the real magic lies. For example, I was interviewing ex-GE CEO Jeff Immelt about his career when he casually slipped in there that he has a really solid personal life in the face of all the tumult in his professional life. So I picked up on that and got to ask him something he never gets asked: How did you manage your marriage during the chaotic period of running GE? (You can see it here at around the 29:30 mark)

3) Dig for anecdotes: Sometimes, the best way to get people to open up in an interview is to offer up a personal experience, which then makes them comfortable to share something more personal themselves. I always say: The first half of an interview is about gaining trust, and then the second half is where the real gems are found. You can't get them to open up without being genuinely curious and asking specific, pointed questions that get them to think of real-life situations that illustrate their point. Most people speak in generic cliches, so you'll notice, a lot of times I ask, "Give me a specific example where you encountered X...." or "What is a situation where you remember applying Y?" Get the anecdote and it makes the whole interview so much better!

As I reflected on this recently, I thought about the idea that one simple question can change your life. For me, that question was, “What does success mean to you?” It forces you to think about what you value most. Is it status? Is it money? Is it achievement? Or is it something deeper? In other words, why do you do what you do every single day? What drives you and what satisfies you?

It’s one question that has a million little questions that sprout from it.

So I decided to ask people on Twitter about the most important question they’ve ever been asked. The responses blew me away.

You can see all the responses underneath this tweet, but I’ve compiled the most interesting ones below:

Polina M. Pompliano @polina_marinova

What's the most important/thought-provoking question anyone has ever asked you?

Here are some of the best responses:

“Which of my current views would I disagree with if I were born in a different country or generation?” — Morgan Housel

“If you woke up tomorrow with no memory of your past but you could still function as a relatively normal human, what would you do with your new start?” — Aaron Josserand-Austin

“If you are so smart, why aren’t you happy?” — Shreyas Doshi

“What have you changed your mind about lately?” — Lucas Napier

“Would you do this if you weren't being paid?” — Dustin Hyle

“What makes you come alive?” — Bret Magpiong

“If this had been my last week alive, am I satisfied with how I spent my time?" — Corey Wilks

“Then what?” — Alex Daniels

"Mummy, should this be my decision or yours?" - my 7-year-old — Ramya Venkataraman

“Do you want to win or to be right?” — Pablo Arosemena Marriott

“What’s the one thing that you wish someone would ask you…that no one is asking you?” — Jason Scott

“Would you rather nudge 100 people or nurture 10?” — Sam Furness

“In what ways are you complicit in creating the conditions that you say you don't want?” — Jonny Miller

“How is avoiding to do X serving you?” — Sabrina Wang

“Would you rather have the ability to look into your future or to change your past?” — Jatin Gupta

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