When choosing interview questions, stay away from weird.

In one of my PhD classes last week, a classmate mentioned that he’d probably interviewed for more than 150 jobs in his life. This led to a brief discussion amongst the cohort about our best (and worst) interview experiences. I did some quick math and concluded that I’ve interviewed for approximately 100 jobs in my life, the bulk of those coming in my last semester of graduate school or during a span of roughly three months after I had quit a particular job more than a decade ago.

I have interviewed for jobs in some of the best times (had four offers upon completion of graduate school) and the worst times (the Great Recession in 2008-09, when I had to take a job—and a pay cut—more than 2,000 miles from my hometown). There was that time a sports organization in North Carolina that I was interviewing with forgot to book my flight, called me the day before my scheduled in-person interview and basically said “Oops, our bad. But if you feel like driving down here, we’d still love to talk to you.” And I did drive down. All night, from Michigan to North Carolina. I didn’t get the job; probably because I could barely keep my eyes open during a conversation with my potential supervisor.   

My strangest interview questions – A personal jobseeker memoir.

I thought it would be appropriate to share five of the worst/weirdest interview questions that I have been asked in my life as a marketing professional. I’m sure others have been asked some pretty odd questions as well.

  1. If you were a vegetable, what kind would you be and why?

Yup, this happened during an in-person interview for a non-profit marketing position. A classmate said that she had been asked a similar question once, but the vegetable was replaced with a box of cereal. I stammered something about being a carrot since I ate so many as a kid that I was frequently compared to a rabbit, but the question definitely made the rest of the interview a fairly painful experience. 

I recommend not using these wacky, meant to catch a candidate off-guard, types of questions. It’s a waste of time and there are better ways to ask questions that allow the interviewer to learn how a candidate sees his/her self.

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  1. Are you comfortable working with mostly men?

I got this question more than once, because I worked in college/professional sports for several years. And I hated it. It’s a no-win situation for a candidate. What are you supposed to say? Sure, I love men! Or, actually, I’m still of the belief that boys have cooties. Of course the candidate is going to respond that they have no problem working primarily with men, they want the job and will say anything to keep the conversation going in the right direction. I always mentioned in my response that I had two older brothers and that the bulk of my youth sports playing experience was coed because of the small size of my hometown, but the question left me uncomfortable and feeling as though I was getting boxed into a corner. Part of me wanted to say, “I don’t have a problem with guys…why, do you?” While there’s nothing wrong with being clear that a company has men in several leadership roles, you don’t want to phrase the question in a way that makes the place sound like it has a glorified boys’ club culture.

  1. If you are hired for this position, you need to be aware that women in the office are not permitted to wear open-toed shoes until they have at least a one-inch heel.


Um, OK? I have no problem with company dress codes (if you think about it, most workplaces do have some sort of dress code policy), but this was such a poorly-worded question (and more than a little discriminating, if you ask me). The sarcastic voice in my head wanted to ask the human resources manager if this meant that men were allowed to stroll about the office in Birkenstocks. Full disclosure: this was for an internship with a professional sports team that I needed to graduate, so I bit my tongue and bought a couple new pairs of dress shoes.

  1. What do you think would be a fitting epitaph on your gravestone? Yikes.

And imagine being asked this question when you’re in your early 20’s and fresh out of college. Double yikes. I remember being very creeped out after being asked this and suddenly aware that this was NOT a place where I wanted to work. There’s got to be a better way to have a candidate share a positive message about themselves. In case you’re wondering, I believe I went with the tried and true Kurt Vonnegut quote: “so it goes.”

  1. Tell me about the worst boss you’ve had.

Warning! I sense danger on par with a group of teenagers splitting up in a horror flick. Don’t do it! There’s no way out. If you go into detail about a former nightmare of a boss, you can appear to be whining or a potential “difficult” employee. Respond that you’ve never had a bad boss, and you’re either lying or being insincere to give the interviewer the answers you think they want to hear. I went with option two: “I’m really lucky, I’ve never had a bad boss or worked for a terrible supervisor” response. And I could feel my imaginary Pinocchio nose growing with every word.  

I should mention that most of these questions were not asked by human resources personnel, but either a potential supervisor or high-ranking member of the company’s marketing/public relations department.

Now that I’ve shared my awkward interview moments, why not take a minute to reflect upon your past experiences as a job applicant. Do you remember any particularly bad (or good) questions that you were asked in the interview process?

At HIRECLICK, we recognize the importance of the jobseeker experience. We encourage our clients to treat potential employees just like potential new clients. Whether they are hired or not, these potential employees make up your jobseeker funnel and may re-apply in the future (if you avoid asking them crazy interview questions).

If you are looking for a truly powerful, yet affordable hiring system, we invite you to try HIRECLICK. Starting as low as $99/mo, it will simplify your hiring process, organize your applicants and save you a ton of time and money.  Take a product tour or contact us to get started.

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