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Interview Questions CEOs Ask, and How to Answer Them

by THEA kelley | June 15, 2023

Got an interview with a CEO? Be ready for odd and off-putting questions. Here are some interview questions CEOs ask, from the LinkedIn Talent Blog, along with my suggestions on how to answer them effectively.

“Tell me something that you believe is true but that almost nobody agrees with you about.”

As an interview coach, I’m appalled by this invitation to shoot yourself in the foot. Peter Thiel, co-founder of Paypal, asks this question because he likes to hire people (in fairly high-up roles, I’m guessing) who have originality and the nerve to say what they really think.

You’ll probably never be asked this in an interview, but if it does occur, I suggest that you not take “almost nobody” literally. You might talk about an unusual approach you have to a technical problem, or a quirky-but-smart opinion you have about something relatively noncontroversial. Avoid politics and conspiracy theories.

Maybe a myth-busting fact would work. For example, “I believe humans have more than five senses.” Many neuroscientists would agree, citing such capabilities as nociception (the ability to feel pain), chronoception (ability to feel the passing of time), and equilibrioception (sense of balance). Maybe Thiel would see this as a cowardly dodge, but at least you’d sound well read.

Unless you’re about to interview with Peter Thiel, I doubt you need to worry about this question.

“How long are you willing to fail at this job before you succeed?”

View this kind of question as an interesting challenge, and above all don’t take it personally.

John Sterling, co-founder of Interview Circuit, asks the question above, and likes to hear an answer along the lines of “as long as it takes to succeed.” If you use that answer, don’t just stop with one sentence. Say a little more about what you mean; put your own spin on it.

Don’t sidestep a question like this. Avoidance can imply a lack of confidence, a touchy ego, or even a disapproval of the CEO’s approach to interviewing.

“How would you describe yourself in one word?”

Whew, a relatively normal question for a change!

Don’t rush into answering, even if you already know what you want to say. When former YWCA CEO Dara Richardson-Heron asks this question, she looks for a thoughtful response.

The best answer, as is often the case, will combine strategy and authenticity, suggesting a quality that’s highly relevant for the role but also deeply characteristic of you as a professional. In other words, look for the intersection between what they’re looking for and your unique strengths.

A candidate for a Business Analyst might answer, “I’m curious. I love to meet people and ask them questions about their lives. I also read a lot, about all kinds of subjects, like (name a few). On the job, I’m curious not only about what various business units do and what data will help them do it, but what the different managers’ day-to-day experiences are like and their personal goals. For example, a few months ago I was meeting with our manager of . . .”

“What’s the most recent thing you’ve learned on the job?”

Andrew Felev, CEO of Wrike, asks this question to get a sense of whether the candidate has a passion for learning. A worker with that attitue is likely to deliver results beyond the minimum, and to keep growing. In your answer, it’s less important what you learned than the curiosity and motivation you showed. What effort did you make to pick up the new skill or knowledge? (Extra points if it wasn’t a required training.) If at all possible, describe how you’ve used the new learning on the job, or how you might do so in the near future.

“What didn’t you get a chance to include on your resume?”

Some CEOs, like Richard Branson of Virgin Group, are skeptical of resumes and want to know what’s behind the careful, polished presentation they’re seeing on paper.

You could tell a STAR or SOAR story you didn’t have room for on your resume, or add some interesting new detail about an accomplishment you did include.

Or you could talk about a leisure interest that you’re enthusiastic about, one that supports the impression you’d like to give. For example, travel experiences  can demonstrate many strong qualities such as resourcefulness, thinking on your feet, problem solving, curiosity, an interest in varied cultures and more. Don’t spell out what you’re trying to convey, though. Let the interviewer draw their own conclusions.

For more tips, read my post, “How to Ace an Interview with the CEO.”

In a later post I discuss five more of these challenging CEO questions, and why preparing for them is useful even if you don’t have an interview with a CEO! Meanwhile, you may want to think about what you’ll say when the CEO asks “What questions do you have for me?”


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