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.

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.

[Image: Flickr user Gonzalo Díaz Fornaro]

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  • The entire interview process is always awful even in the best of circumstances. I've had interviewers do worse. Once after jumping through hoops to land myself as a top choice the interviewer wanted to know my birth month, day & time so she could consult her vedic (?) astrologer to decide...I was thinking she could have asked that before wasting everyone's time. Another one asked me to interview at the same time as another candidate because he was hungry & wanted to leave for lunch earliers. Glad I became an ind contractor.

  • My wife recently interviewed a "veteran manager" who was applying for an assistant management position at a large multi-family community. The applicant had only three questions during the interview.

    1. How many paid holidays do I get?
    2. How many paid sick days do I get per year?
    3. How long do I have to work before I get a paid vacation?
  • Mel Kleiman

    This are not bad or strange qquestions they are great questions they tell you not to hire the applicant.

  • Bruce Yail

    okay number 8 I dont get, I mean she was on her lunch after all you only get one chance to eat a day at most places

  • Larry Berry

    Yeah, I'm with you on that one. The fact that she was doing the interview on her lunch break shows she's a hard worker. Provided the rest of the interview was good.....

  • Oh I got some good ones, too! During an interview for a PR internship: "What is PR?" and "What is a media list?" And the evergreen, but now on steroids: "When (when not if) I get hired on, will I have health insurance? Because I have some big health issues and I am frequently at the doctors, so health insurance is very important to me."

    But really, nothing can top "Is your boss single?" Nothing! Laughed out loud!

  • I think the diminished expectations on the candidate's part from repeated rejection is at least partially responsible for this type of behavior. That, and just being a poor fit for the environment in the first part.

    Many years ago during the Dot-Com crash, I was conducting a technical interview with a candidate whose presentation was eccentric, to say the least. While it was/is not unusual in Austin for technical jobs to have a casual atmosphere, this fellow was woefully unprepared for the entry-level position but was either blissfully unaware or supremely optimistic. At the end of the interview, he said that to stand out from the crowd of candidates we would see, he would like to present a non-job-related skill. Intrigued by the strategy, I inquired what he had in mind. He asked if I would prefer for him to present an intact geode and predict its color before cracking it open, or to give a recital on his Native American flute. Thanks, but no thanks.

  • Linda Rizzo

    Bad behavior works both ways. A few years ago I had an interview with the owner/CEO of a large Canadian-based apparel company. My interview began at 7:00 in the evening (his choice) and apparently this was also his dinner time. He had me sit next to him at a conference table while he ate a stinky fish dinner. Then midway during the interview he asked if I was married. I was taken aback by the question but answered no. He then asked if I "fooled around". I was offered the job, but declined.

  • Reina Seaton Smyth

    I once had a woman answer her cell and proceed to have a conversation with the person calling during an interview. When I saw her reach for the phone I initially thought she was going to silence it, but then she answered it and I thought "well okay maybe its an emergency with a family member or something". Nope, it was about her plans with her boyfriend for that evening. She also said she wasn't available to work on Wednesdays because traffic was bad on Wednesdays. I'll never forget that interview.

  • Stephen Q Shannon

    Would it be okay if I lie down when I keyboard a comment here? This article, if only half true, is a keeper. Thanks for making my day, week, and month. sQs Delray Beach FL