9 Revealing Job Interview Questions Top CEOs Ask (That You Can Ask Too)

9 Revealing Job Interview Questions Top CEOs Ask (That You Can Ask Too)

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1. "What do you like to do for fun?"

CEOs love this interview question because it "always speaks volumes of who that person is. This question can determine a cultural add within the company and tell more about who a candidate is—through and through. How to Answer This Style of Question: This is a culture fit question through and through. The

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1. "What do you like to do for fun?"

idea behind these is that you should know the company and have considered whether you'd make a good addition to the personalities there. The best way to prepare for these sorts of questions is to do your research thoroughly. Because if you really loved Warby Parker, shouldn't you know that they like their team to have a little fun? (I mean, those glasses look fun).

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2. "Tell me about some of the most difficult problems you encountered."

This is a pretty common interview question, but you want to make sure to have an impressive answer. The CEO likely wants to know which of your characteristics came into play when faced with a high-stakes problem. How did you address the problem? How long did it take? Did you take a leadership role to solve the issue? What was 

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2. "Tell me about some of the most difficult problems you encountered."

the outcome? Using story circles and the STAR method is a great way to "write" these stories from your perspective so that you're ready to tell them in an interview setting. How to Answer This Style of Question: Know yourself and prepare to answer questions about problems and mistakes—they 

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2. "Tell me about some of the most difficult problems you encountered."

come up more frequently than most job seekers expect. Also, feel free to pause and linger on a question when it's hard-hitting like this.

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3. "Tell me about your background."

A deceptively simple and all-too-common interview question, this is a common question for a very good reason. It’s a great way to warm up any conversation, and it really helps me understand how you communicate. Are you linear, concise, and direct? Or are you a storyteller? Are you entertaining? Do you go off on tangents?

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3. "Tell me about your background."

How to Answer This Style of Question: Think about the company's values, your biggest accomplishments, and the recent events in your career that led you to this interview. If you want to sprinkle in a few fun facts about yourself, then share those, too!

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4. "Tell me about this [XYZ] career decision or career transition."

Apparently, former SoulCycle CEO Melanie Whelan also likes to ask questions about career transitions to see how interviewees approach them. "Were you running away from something or toward something, and how do you frame that?" How to Answer This Style of Question: Know your personal pitch and 

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4. "Tell me about this [XYZ] career decision or career transition."

know how to tell a story well. That includes being able to talk about gaps in your resume or shifts between industries.  If you're not comfortable talking about yourself, you need to work on it either with friends or by joining a local Toastmasters or something of the sort. This is a type of public speaking and how you articulate your background is absolutely key.

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5. "Give me an example of a time when you solved an analytically difficult problem."

This is what you might call a "behavioral" interview question. Here's how Laszlo Bock, CEO of Humu, explains behavioral interviewing to the New York Times: "'You're not giving someone a hypothetical, but you're starting with a question like, 'Give me an example of a time when you solved an analytically difficult problem.'"

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5. "Give me an example of a time when you solved an analytically difficult problem."

"You get to see how they actually interacted in a real-world situation, and the valuable 'meta' information you get about the candidate is a sense of what they consider to be difficult." How to Answer This Style of Question: Don't be afraid to get real, in fact, that's the point. Pull an actual example from the last 

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5. "Give me an example of a time when you solved an analytically difficult problem."

few months. If you're not self-reflecting on your work, you should be. One way to do this is to start keeping a work journal of your successes and failures right now.

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6. "If you find yourself in situations where they're not going the way you want them to, what do you do?"

According to an interview with the New York Times, TIAA Financial Solutions CEO Lori Dickerson Fouché—uses this question to gauge how a candidate conducts themselves under pressure. She also asks:

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7. "Describe some difficult leadership situations and how you managed people through them."

This is a question CEOs ask for higher-level positions to gauge "how they make their own hiring and firing decisions." How to Answer This Style of Question: These may seem like different questions, but according to Fouché, each focuses on "perseverance and resilience"—great qualities to have especially at the bigger 

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7. "Describe some difficult leadership situations and how you managed people through them."

companies where she's worked. Approach these with a critical eye. Explain how you work, but also why. And don't be afraid to mention a moment where you misstepped early on. Share how you learned something essential about how you work or how you lead.

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8. A Curveball: "Find out how they treat others."

No, this isn't a question for you. It's for the receptionist who you checked in with and maybe the person who rode the elevator up with you, too. Sometimes, the best way to understand a job candidate is to ask people how they behaved when it didn't occur to them that anyone was paying attention. It's a way to get "a sense of the 'non-cognitive 

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8. A Curveball: "Find out how they treat others."

skills' that good leaders need to manage and inspire teams. Pay Attention to CEO's Treatment of Others: This is an even more important question for you, the candidate, to consider. How a CEO treats others trickles down to other senior management and it becomes interwoven with the entire company culture. Maybe this isn't as important

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8. A Curveball: "Find out how they treat others."

to you. Perhaps you'd love to work for a "mad genius" type of CEO who gets kicks from being demeaning to baristas.

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9. Horror Stories: "Describe a failure in your career."

Mistakes happen. Yes, they do—and it's ok. It's what you learn from your failures and mistakes that makes a big difference. CEOs ask this question to determine how a potential employee approaches and overcomes problems.  This also can illustrate the candidate's ability to take responsibility,  bounce back, and refocus after problems 

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9. Horror Stories: "Describe a failure in your career."

occur. This is a great question to ask because it takes the CEO out of their current role of power. It allows for vulnerability (depending on their willingness to answer!) and real insight into how this leader handles some of their own biggest challenges. How to Do This Right: Next time you're going out for interviews, make sure you have 

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9. Horror Stories: "Describe a failure in your career."

your best failure ready—and your step-by-step recourse that you followed after the failure. How did this failure inform how you moved forward? What actions do you take to ensure that it doesn't happen again?

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