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Have you ever got interviewed by the CEO or the big boss of a company? Yes? How does it feel? How different are the sensations from the regular job interview that you have with the hiring manager? Well, I think the difference is huge, because the CEO will hopefully not bother testing your skills but surely would want to know how fit are you for his company, so one never know what will he ask.
Anyways, for those of you who said No, and haven’t ever experienced an interview with the CEOs, here we are with some of the trickiest questions asked by some of the CEOs. Read these to get the fair idea:

featured image-big boss

1: “What was the recent costume you wore?”

This question was asked by Neil Blumenthal, Co-CEO of Warby Parker. He says, that the idea behind this question was not to know whether the candidate even wore any costume or not. But, it is to see how the candidate would react to it. If you take yourself seriously on this, then you are probably not the right pick for the company as it expects you to take your work seriously and not yourself.

You too might be asked such bizarre questions which would intend to assess your suitability for company culture. So, don’t worry about what to answer just focus upon how to answer.


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2: “What was in the newspaper that day? Share anything you know or feel about it.”

Deborah Bial, President of the Posse Foundation asked this question in an interview. This is like a discussion question, which intends to know how interesting you are as a person instead of how efficient you are as an employee.

If you too are being pulled in such discussion, then do not just think before speaking, but also keep a check on how he is responding to your answers. You might have to modify your answer as per his reactions.


  1. The Real-World Problem

Jane Park, CEO of Julep, said that she mostly ask about the real problems that she struggles with. This makes it easy for her to analyze weather the person can be her partner in visualizing strategies and executing them or not. Also, she can identify the engagement & curiosity level in the candidate.

Well, such questions are good for you too, as you can then judge whether the job interests you or not.


  1. “Summarize your life in 3 minutes.”

Similar to ‘Tell Me About Yourself’ question, Brian Chesky, CEO of Airbnb, had asked this question to one of the candidates he interviewed. He says, “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.”

If you are asked for a similar question, then focus on the meaningful & relevant experiences and highlight them in a manner that even makes sense for the position you are applying for.  It’s better that you be ready with such answers beforehand. You may look up for how to structure answers for interviews for the better idea.

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