The 1 Question I Asked A CEO In An Interview That Got Me The JobExecutive Communityon November 27, 2023 at 5:51 pm Work It Daily


Years ago, I was interviewing for a job. As many of you know, when you go through the interview process, you start with the recruiter, and then you meet with the manager, and then you meet with some of your peers—if you’re lucky. Then, at the end of the interview process, you might meet with the highest-ranking executives. So in this case, I met with the CEO.

I knew I was doing okay because I was getting through each round of interviews. So, I go into the CEO’s office. I don’t know what to expect. It’s a startup company. He’s sitting there in a t-shirt and sweatpants. He’s eating cereal and has his feet up on his desk. He says, “Come sit down.” Then, he proceeds to interview me while he eats cereal, his feet still up on the desk.

There I am in my suit, answering all the questions, and, finally, he asks, “So do you have any questions for me?”

And I said, “Yeah. What keeps you up at night?”

“What Keeps You Up At Night?”

The CEO stops eating his cereal, looks at me, and says, “I’m sorry. What?”

I respond, “When it comes to this business, what is keeping you up at night about its success? And how will the job that you’re considering me for, how will the job that I do, impact the ability to solve for that?”

His face goes blank, he takes his feet off the desk, and he puts his cereal down. My heart starts to pound. Then, all of a sudden, he turns and looks at me. He leans in and says, “Hmm, let me think about that.”

Now I’m thinking, “Oh my gosh, I just blew it.”

Then, he gets really serious and starts to explain how this job impacts that ability. Then, he starts singing. Eventually, the interview ended and I went home thinking, “What did I just do?”

I got myself a job.

He told them that I should be hired because anyone who understands that their job impacts every level of the organization—and that they should be thinking about that impact—understands the value of the work that they need to do, and would do a good job. That’s what he told the hiring manager. And the hiring manager told me.

So that gamble paid off. It not only taught me how important it is to ask questions in an interview but also how important it is to ask the right questions to the right people.

If you want to stand out in the interview process and land the job, try asking this question in your next job interview. It’s all about understanding and relieving an employer’s pain points.

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