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 interviwers 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?

7:27 PM ∙ Jan 4, 2023

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221Likes30Retweets

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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THE PROFILE DOSSIER: On Wednesday, premium members received The Profile Dossier, a comprehensive deep-dive on a prominent individual. It featured James Patterson, the best-selling author on the planet. Become a premium member, and read it below.

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The Profile Dossier: James Patterson, the Best-Selling Author on the Planet

As the best-selling author in the world, James Patterson is a hit-maker. He knows how to capture a reader’s attention — and hold it — for hundreds of pages. Patterson is as much a writer as he is a business. He has published more No. 1 New York Times…

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4 days ago · 7 likes · Polina Pompliano

PROFILES.

— The professional cyclist whose death became a spectacle [**HIGHLY RECOMMEND**]
— The Tom Brady of other jobs
— The NBA star healing invisible wounds
— The company making learning languages fun
— The elite nanny school
— The world’s most dominant ticketing company

PEOPLE TO KNOW.

The professional cyclist whose death became a spectacle: For a few short years, Moriah Wilson took gravel racing by storm. The 25-year-old was a champion in her sport. And then her family received the devastating news: Their beloved daughter had been shot and killed in Austin, Texas, the night before. From there, Moriah’s name began to ricochet around the world at the center of a plot that felt utterly disconnected from the person she had been with the words “love triangle” plastered on every media article. This is a must-read. (Bicycling)

“The temptation to fit the suspect into the frame of Mo’s life is a tragedy that compounds the loss.”

The Tom Brady of other jobs: In the NFL, Tom Brady is considered a very old man. Starting at quarterback at 45 is akin to being a family doctor well into his ninth decade. It’s like being an emergency medical technician — a job that requires running up stairs and lifting bodies on stretchers — at age 70. Or an artist in her 90s, a logger in his 80s or a biologist in her 70s. Meet the American workers who occupy the same part of the age distribution in their professions as Mr. Brady does in his. (The New York Times)

“When I started out, when I was young, I always wanted to have a rich life. And brother, have I.”

The NBA star healing invisible wounds: NBA player John Wall says six words saved his life: “Yo! I need some f***ing help!” In the span of three years, he went from being on top of the world to losing nearly everything he had. He dealt with a bad infection to surgeries to the monumental loss of his mom. In this deeply personal story, Wall opens up about the importance of raising your hand when you need help. (The Players’ Tribune)

“Bro, how the hell can you have all that money and be depressed? You’re John Wall.”

COMPANIES TO WATCH.

The company making learning languages fun: Duolingo is the free language app that has gamified learning French, Gaelic and even High Valyrian. Now the public company must make money without infuriating its fierce following. Twitter co-founder and dedicated user Biz Stone summarized Duolingo’s unusual duality in an April tweet: “The gamification on @duolingo would be evil if it weren’t for a good cause.” (Bloomberg; reply to this email if you can’t access the article)

“It’s not like I’m against making money, but it has never been a top priority. If you do things that are impactful, then money will follow.”

The elite nanny school: Norland College is one of the oldest and most prestigious nanny schools in the world. Most, with only a few years in the field, can expect to fetch six-figure salaries, looking after the offspring of bankers, royals and celebrities, either working independently or joining a carousel of domestic staff — private tutors, housekeepers, chefs — that serve the globe-trotting elite. Take a look inside the institution that offers courses on early childhood education and cooking alongside learning to fend off kidnappers and shielding strollers from paparazzi. (The New York Times)

“Our nannies know exactly how to react in a way that deters the aggressor and keeps the child calm.”

The world’s most dominant ticketing company: Ticketmaster faces a class-action lawsuit from Swift fans accusing it of fraud, misrepresentation and antitrust violations over its botched Eras Tour ticket sale. The DOJ has opened a broad antitrust investigation of Ticketmaster parent Live Nation. But Ticketmaster has been scrutinized many times before. “History continually repeats itself,” said former Ticketmaster CEO Fred Rosen. Ticketmaster’s maligned fees and customer service issues are again under the microscope. Will American music fans ever see anything better? (The Hustle)

“Your choice becomes do a deal with them and do this tour, or don’t and don’t tour.”

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