87 Revealing Job Interview Questions From Hiring Managers In Business And Tech – CB Insights Research

We asked, you answered: here are 80+ of the favorite interview questions from hiring managers.

Where is this data coming from?

We asked our newsletter readers (hundreds of thousands of professionals working in tech, investing, startups, and corporations across the world) for their favorite job interview questions.

We put them together in one post as a public service to improve job interviews everywhere.

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Of course, a note of caution is needed here: best practices dictate most of a job interview and assessments should be focused on skills and knowledge areas related to the job. Too many out-of-the-box questions can inject bias into a process. Still a curve-ball is often a good way to get to know a candidate better.

Personality and/or self-awareness

Clarity of thought


Career aspirations

Fit & aptitude


Interview anecdotes

Gimme a break…

Our office manager asked candidates: “If you were a candy bar, which candy bar would you be?”

One quick-witted interviewee said, “A 100 Grand Bar because I want to make six figures.”

Fake news

I ask candidates how they would prove to someone that the moon landing actually happened, that it wasn’t faked.

Last week, I met someone that doesn’t believe we’ve ever been to the moon. I was … speechless.

Lie to me

I had a manager who had previously worked in HR, and she told me that there is always one lie or omission on any CV submitted for a job interview. It’s usually worth asking what that lie is, and go straight to the confessional.

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I’ve used this strategy in 50+ interviews and had an interesting confession out of at least 40 of them. I tell the interviewee that we know that every CV contains an omission or a lie, and to save everyone time we’d like to know where it is and get passed it. We get confessions about unexplained gaps, short employments that failed and were left off, even a brief sojourn in prison. (I employed the ex-convict, and she turned out to be a perfect employee who appreciated the extra trust that came with the confession.)

It’s worked as a strategy for us.

What we want

I ask, “What three things do you think we are looking for?” It sounds standard and simple but I have yet to hear anyone who answers with confidence.

Hair ye, hair ye

I ask every candidate I interview to teach me something. I have added this to my interviewing routine for a couple of reasons: it’s usually an unexpected ask, so I get to see how they respond to a surprise, and it gives me a window into how they share information about a very comfortable subject for them.

The most memorable teaching lesson I have experienced was learning how to apply a balayage hair treatment. It was during an interview for an entry level marketing position. The candidate was so thorough and I knew that even though she didn’t have the marketing experience required for the job, she had an attention-to-detail mindset so I hired her. She was one of the best hires I’ve made.

Flip it and reverse it

To turn the tables on you: if I were one of your interviewees, I would ask you, “What systems and structures do you have in place to ensure my success in your organization?”

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