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5 More Interview Questions CEOs Ask, and How to Answer Them

by THEA kelley | June 22, 2023

In last week’s post I explored five tricky interview questions CEOs ask–or at least some CEOs. Now let’s look at five more, and I’ll offer suggestions on how to answer them.

While you may never have to field these particular queries, thinking about them is a good way to stretch your interview skills. Once you’re ready for these, you may find you’re less easily flustered by unusual interview questions in general.

Also, it’s not only CEOs who ask questions like these. The first, in particular, is fairly common.

“So, what’s your story?”

This question is pretty common. One CEO who asks it is Richard Funess, managing partner of Finn Partners, a marketing agency. He believes it can reveal a lot about the candidate’s “character, imagination and inventiveness.”

“The way they look at me when the question is asked also tells me something . . . If they act defensive, look uncomfortable, and pause longer than a few seconds, it tells me they probably take things too literally.”

So your willingness to play along may be as important as what you say!

But let’s think about what to say. Try this:

  1. Ask yourself, What is (a) surprising or intriguing about my background, and (b) the #1 reason why they should hire me?
  2. Plan an answer that opens with (a) then quickly segues into (b).

For example, let’s say you’re a math wiz who somehow found your way into communications. That’s intriguing. And maybe your “why they should hire you” is your unique combination of data-driven thinking and a talent for managing creatives.

“Nobody ever thought I’d end up in communications. In high school I majored in math and entered every STEM competition I could find—did pretty well in them, too. But once I got into the business world I found my interest moving from the numbers to the customers. What did they want, and how could we communicate that we had it? I became a data analyst with XYZ, then a manager. I discovered I loved the creative side of marketing, and managing writers and graphics people–and actually, there’s a story I could tell you about how I ended turnover in my group and developed them into a highly respected team—so the role we’re talking about today is my dream job.”

(Notice that this answer includes a “teaser” about “a story I could tell you.” That’s a good way to gain credibility with an example, without making your answer too long by telling the story. They’ll very likely ask for that story next, or you can bide your time and tell it later in the interview. This is one example of a technique I call “expandable answers.”)

The main thing here is to avoid is a boring summary of your resume.

“What percentage of your life do you control?”

Ready to get philosophical? You’d better be if you interview with Mitch Rothschild at Vitals.

You probably don’t need to give a number, nor should you wander into the academic weeds of free will versus determinism. You do need to really think about it, show some curiosity and make it clear that you believe in your power to make a difference.

Rothschild says he looks for people who can make change happen. Who wouldn’t?

“What’s in the newspaper today?”

No, it’s not a current events quiz, though you should show a healthy awareness of what’s going on in your industry and the world. The CEO who asks this one, Deborah Biel of the Posse Foundation, uses it to open a general conversation that gives her a feel for how the candidate thinks and communicates.

“What makes you special?”

If you don’t know, you can’t expect the interviewer to figure it out. One of the first things you need to do as a  job seeker is determine what makes you stand out.

Penny Herscher, former CEO of First Rain, believes this question helps her measure a candidate’s energy, intelligence and integrity. So a successful answer would be creative, strategic and authentic.

“Imagine you’ve just had the greatest working day of your life. You’re driving home and you’re on cloud nine. What about this work day made you so happy?”

If you have a good answer to this question, find a way to weave it into your interviews even if you aren’t asked. For example, it might be a great addition to your “Tell me about yourself” answer.

This question came from Lew Cirne of New Relic, who is convinced that people excel when they love what they’re doing. I certainly agree–don’t you?

The interview questions CEOs ask can be quite surprising. Arrive at a CEO interview with plenty of energy, a sense of humor and a ready-for-anything attitude.

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