For most positions, it’s unlikely that you’ll actually be interviewing with the CEO or president of a company. But, in case you ever do have a one-on-one with the big boss—or are meeting with someone who strives to interview the same way—why not be prepared?

Here are five real interview questions from chief executives pulled from the New York Times’ Corner Office interviews—plus some tips on how to best answer them.

1. The Elevator Pitch

Brian Chesky, CEO of Airbnb

I also ask people to summarize their life in three minutes. I’m trying to figure out the formative decisions and experiences that influenced who you are as a person. Once I figure that out, I’m trying to understand the two or three most remarkable things you’ve ever done in your life.

This variation of the standard “Tell me about yourself” emphasizes life accomplishments. So, even though you’re asked to summarize, what you’re really doing is picking out a few relevant or meaningful experiences to highlight in a structured manner that brings it all back to why you’re interested in this particular position and company. To get a better idea about how to structure your answer, watch this quick video.

2. The Real-World Problem

Jane Park, CEO of Julep

I often give the person a real problem, whatever I’m wrestling with right now, because you can learn a lot about a person that way. Are they going to be my partner and be able to see the strategic issue as well as how to execute on it? Are they interested and engaged and curious about it?

It’s really fantastic when interviewers present real-world problems as part of the interview. What could be a better indicator of whether or not you’re capable of doing the job—or even interested in it? If you are technically qualified, you will be fine with this type of question. Just make sure you are mindful of how you are presenting your solution. To be clear, start with a general statement about what you think the solution might be (or at least the general direction you’re going in), and then support it with your thought process or reasoning. Of course, feel free to ask for more information or to see what your interviewer thinks about various aspects of the problem. Even the types of questions you ask will be revealing about how you think.

3. The Unspoken

Kat Cole, President of Cinnabon

Part of the process starts before the conversation. How do you interact with people in the waiting area? I’ll ask people to offer the candidate a drink to see if there’s a general gratefulness there, and they’ll send me notes.

Then, when someone walks into my office, I’ll have a big wad of paper on my floor between the door and the table. I want to see if the person picks it up. I don’t make huge judgments around it, but it does give me a sense of how detail-oriented they are.

The tips for this particular interview—erm, assessment—are pretty straightforward. Every interaction you have with the company you’re interviewing with should be considered part of your evaluation. This includes the emails you send to schedule the interview, the conversation you have with the person sitting at the front desk, and the thank you notes you send. These all add up to inform the decision the hiring manager ultimately makes.

4. The Airport Test

Deborah Bial, President of the Posse Foundation

I’ll want to get into a discussion about something. What’s in the newspaper that day? I want to know what they think, how they think, how they express what it is they’re thinking, how they ask questions and how they listen.

The Airport Test is essentially a question that attempts to weed out people who would be unbearable to be stuck in an airport with. It’s a question that tries to assess how interesting you are as a person, rather than how effective you are as an employee. Be ready to share your opinions and passions—the more unique, the better. Just don’t forget you’re still in an interview. This means gauging the response of your interviewer and responding appropriately. Is the topic of interest? Is it kind of offensive? Does the interviewer have an opinion on the topic, or is he or she just listening politely?

5. The Fit Question

Neil Blumenthal, Co-CEO of Warby Parker

One of our core values is to inject fun and quirkiness into everything we do. So we’ll often ask, ‘What was a recent costume you wore?’ And the point isn’t that if you haven’t worn a costume in the last four weeks, you’re not getting hired. It’s more to judge the reaction to that question. Are you somebody who takes yourself very seriously? If so, that’s a warning sign to us. We want people to take their work seriously but not themselves.

Unusual questions like this are often a guise for assessing your fit with the company culture. As Blumenthal states, it’s not so much about what your answer is, but more about how you answer. Tackle these strange questions with enthusiasm, regardless of how satisfactory you think your answer is, and you’ll have won half the battle.

Photo courtesy of Silicon Prairie News.

Updated 6/19/2020