What It’s Like to Be Interviewed By Steve Jobs, Elon Musk, And Anna Wintour

As much as you can prepare for the standard interview, it can all go out the window when you are speaking to a legendary boss.

What It’s Like to Be Interviewed By Steve Jobs, Elon Musk, And Anna Wintour

Sitting across the desk from a hiring manager is nerve wracking enough, but imagine if the person doing the interviewing is a business legend like Elon Musk or Anna Wintour? “Nerve wracking” is an understatement, and standing out from the competition presents a special challenge.


“Top CEOs look for three things when they hire people,” says Sydney Finkelstein, author of Superbosses: How Exceptional Leaders Master the Flow of Talent. “The first is intelligence, but not just IQ; they’re looking for social abilities, relationship building, and emotional intelligence. They also look for creativity. Do you have a track record of thinking about things differently? And finally, they want someone with extreme flexibility. What kinds of projects did you take on, and how did you rise to the occasion?”

Business greats often have unique methods for uncovering these traits, says Finkelstein. Oracle founder Larry Ellison was known for asking candidates, “Are you the smartest person that you know?” “If they said ‘no,’ he’d ask who was, and then he’d immediately say, ‘Thank you very much,’ dismiss the person, and contact the person the candidate had mentioned,” says Finkelstein.

Photo: Dan Taylor/Heisenberg Media

An Interview With Elon Musk

Elon Musk told Auto Bild TV that he’s interested in learning how candidates dealt with past problems. “Did they face really difficult problems and overcome them?” he said in the interview. “And then, of course, you want to make sure that if there was some significant accomplishment, were they really responsible or was someone else more responsible? … You can ask them very detailed questions about it and they’ll know the answer, whereas the person who was not truly responsible for that accomplishment will not know the details.”

Software engineer Jeff Nelson interviewed with X Commerce (which later became PayPal) in 1999, and calls his interview with Musk exceptionally conversational. Musk asked just two questions: “What do you want to be doing in five years?” and “Do you have any questions for me?”

“[The first] is one of the most common interview questions that everyone asks. I think I said something about wanting to advance to management,” writes Nelson on Quora.

To answer, “Do you have any questions for me?” Nelson inquired about the risks inherent in the X Commerce business model, since the business was relying on its own competition for payment processing. “Elon, as I recall, said something about growing big fast, so the payment processors had too much money at stake to stop doing business with them,” writes Nelson, who says he was offered a job but declined because the rate wasn’t sufficient.

Photo: Flickr user matt buchanan

An Interview With Steve Jobs

In 1997, Steve Jobs interviewed James Green for a position at Pixar Animation Studios. Green, who is currently CEO of the search retargeting company Magnetic, was working for the Walt Disney Company in Asia, and Jobs wanted to hire someone to serve as liaison between Disney and the producers at Pixar.

The interview was held at Jobs’ home and felt more like a conversation, recalls Green. Jobs told Green that he was looking for someone to manage the relationship between Disney and Pixar. “He asked me if I was interested in being a liaison, and I can’t believe it, but I said ‘no,’” says Green. “All my life Steve Jobs had been an idol of mine, but I told him that it was not a job I would recommend anyone doing; having middlemen never works.”

Jobs then offered Green a job managing the marketing for Pixar’s short film department. “I said, ‘I would love to do that,’” Green recalls, but during the first week of work, he realized that his responsibilities were exactly the job he originally declined.

“You can’t say ‘no’ to Steve Jobs. I did and I still got that goddamn job I didn’t want to do,” says Green, who resigned a few months later.

Finkelstein says the top CEOs are intrigued by candidates who aren’t afraid to push back. “Have a point of view and be unafraid to disagree with what you’re hearing,” he says. “Superbosses respect, admire, and value people who can do that. They’re looking for people who can change the world.”

Photo: lev radin via Shutterstock

An Interview With Anna Wintour

Journalist Amy Odell was interviewed by Vogue editor Anna Wintour, and shares the experience in her book, Tales From the Back Row: An Outsider’s View from Inside the Fashion Industry.


“If I have to interview with Anna Wintour, how will I speak actual words to her face? And what on God’s/her great earth am I going to wear?” she writes in her book.

Wintour asked Odell standard interview questions about her job history and goals, then asked what Odell does on the weekends. Odell had been told by a friend that this question would probably be asked and she had prepared an answer, but Wintour also asked Odell if she enjoyed going to museums and what the last exhibit she had seen was. This was something for which Odell hadn’t prepared.

“I was probably in there for less than 10 minutes. As I stood up, Anna walked around the desk to shake my hand. When she got to me, she looked me up and down in this really obvious prolonged way, probably to make sure that even if I’m some ignorant loser, I was at least wearing an acceptable outfit,” she writes.

Odell didn’t get the job. “Be prepared for a deep dive into anything related to that company or into the interests of the person you’re being interviewed by,” advises Finkelstein. “And make sure you can think on your feet quickly.”

Related: Have You Mastered The Art Of Interviewing?