8 Of The Strangest Interview Questions Job Candidates Have Asked

We’ve established that hiring managers ask some bizarre questions, but some job seekers have a surprising amount of chutzpah too.

8 Of The Strangest Interview Questions Job Candidates Have Asked
[Image: Flickr user Gonzalo Díaz Fornaro]

If you’ve ever squirmed in an interview when your potential boss asks “If you were a box of cereal, what would you be and why?” then you know that some businesses are transforming the interview process as they seek to get past the well-rehearsed answers.


But hiring managers don’t have a monopoly on catching someone off guard. Not all interviewees are on their best behavior.

These brave current and former hiring managers are opening up to share the most eye-popping questions job candidates have asked them.

1. Can mom come, too?

When Ron Culp called his interviewee’s name at the Chicago office of public relations firm Ketchum, two women stood up. Now head of the PR and advertising master’s program the DePaul University, he recalls being confused until the younger woman held out her hand and introduced herself–and then introduced her mother.


Mom asked if she could attend the interview, too, because her daughter was shy and might forget some things. Culp declined, suggesting that the mother go grab a cup of coffee at Starbucks or head over to nearby Macy’s for some shopping for an hour, “even though I had a feeling the interview wouldn’t be that long,” he says.

2. Would you pay me less so I can stiff my ex?

Kari Warberg Block, founder and CEO of Bismarck, North Dakota-based natural rodent repellent maker Earth-Kind was interviewing someone who’d worked successfully for the company for a couple of years, so she thought it was just a formality. The part-time employee was finishing up his master’s degree and wanted to take on a leadership role at Earth-Kind. During the interview, he asked Block, “Could you not pay me a living wage?” Surprised, she asked him why and replied, “Well, I’m going through a divorce and anything I make will just go to my ex,” she recalls. He didn’t work for the company in any capacity after that, she says.

3. Mind if I stay for lunch?

Tom Gimbel, president and CEO of LaSalle Network, a Chicago-based staffing and recruitment firm, sent a candidate for an interview at a client’s office. One of the perks was that lunch was delivered every day for employees. The candidate asked if he could stay for lunch. “The client thought he was joking and laughed. But the candidate said, ‘No, really. Can I stay for lunch?’” Gimbel says. Gimbel has also had candidates show up drunk and one even wore a Snuggie to interview with his firm because she was cold.


4. Is your boss single?

Early in her career, Carol Cochran, director of human resources for Boulder, Colorado-based job search site FlexJobs, was working for a startup company with two young founders. At the end of the interview with one woman, Cochran asked her if she had any other questions. The candidate replied, “Just one thing. The one owner–is he single?” Cochran said he wasn’t, then asked why the candidate wanted to know. “She said, ‘He’s really hot,’” Cochran recalls. “All I needed was for that to get back to my boss’s wife!”

5. Are you going to eat that?

Dilini Imbuldeniya, chief people officer at Sky Zone, a Los Angeles-based trampoline park company, was interviewing a candidate for the company’s controller position. As they walked past the kitchen, the candidate stopped and asked if he could grab some of the snacks that were on the counter. Imbuldeniya agreed and the candidate, “proceeded to help himself to food, candy, and gum that was on the counter in the kitchen. Then he sat down in the interview, start answering questions, and then pulled out his phone to look at who was calling him in the middle of answering a question!” she recalls.

6. May I bark at your dogs?

The Venice, California, office of Lettuce, an online inventory and order management company, is dog-friendly and it’s not unusual for the canine brigade to be running in and out of meeting rooms, greeting candidates. CEO and cofounder Raad Mobrem was interviewing a prospective employee when the candidate stopped in the middle of the interview and asked, “Is it okay if I bark at your dogs?” Mobrem says he sat there, not knowing how to respond, and the candidate started barking. “When we asked him what he was doing, he said it was to show his dominance,” Mobrem says.


7. When will my drug test be clean?

Before he was the staffing business development leader and CMO of Wakefield, Massachusetts-based Eliassen Group, Tom Hart was the chief information officer for a large financial services company and was interviewing a candidate for an executive assistant position. The woman was also a candidate for a flight attendant position at a major airline. As the interview concluded, the woman wanted to know if she could ask Hart a personal question. He agreed and she asked, “If I smoked pot yesterday, would it register on a drug test tomorrow? The airline says I need to pass a drug test before they’ll consider hiring me,” he recalls. “I said it would show up, and wished her good luck with that,” he says.

8. Is it okay if I eat my lunch while we talk?

David Lewis, president and CEO of OperationsInc, a Norwalk, Connecticut, human resources consulting firm, was interviewing a woman on her lunch hour. After about five minutes, she stopped the interview and said, “I’m sure this isn’t a problem, but is it okay if I eat my lunch while we talk? I’m here on my lunch hour.” He said it was okay and, “she proceeded to make a little landing area at the front edge of my desk for bagged lunch, bottle of water. I couldn’t wait to finish so I could tell that story for the rest of my life,” he says.


About the author

Gwen Moran is a writer, editor, and creator of Bloom Anywhere, a website for people who want to move up or move on. She writes about business, leadership, money, and assorted other topics for leading publications and websites


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