Say What? Wacky Interview Questions from the Trenches

By Maren Hogan

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Have you ever stopped and thought about how strange interviews are? Probably not, because it's built into your daily practice as an HR professional, and common practice for anyone looking for a new job. It’s sort of insane that we haven’t come up with anything more than a glorified meetup to determine if we want to meet with someone.

Here at Red Branch Media, we work with both recruiters and HR professionals and candidates, jobseekers and employees, so we get a pretty well-rounded of view of what the workday looks like, around the country and around the world. So, we decided to ask our network what the weirdest interview question they’ve ever received is:

Privacy Concerns and Working Moms?

“Do you have a private room with a door that locks?” McKenna Slack, a recruiter for Triage Staffing was taken aback by this question that popped up during an interview. Depending on who’s doing the asking, it can seem a little…strange?

“This question was completely out of the blue. With no other content or set-up you can imagine why I thought this questions was strange. Turns out she was nursing and wanted to ensure she’d have a private place to do so.”

Of course, since 40% of head of households are female, and growing, chances are some recruiters may get asked this question. Better yet, volunteer the info during the hiring process or on your culture page. According to, 90% of employees have left work due to family responsibilities and more than 40% say the lack of family care benefits impacts their job performance. Care-related productivity loss costs American businesses tens of billions annually.

Headed back to work and unsure of your rights as a breastfeeding mom? Here’s a great primer. (Hint: You don’t have to use a bathroom stall).

Riddle Me This

For every recruiter, think tank leader and CHRO we work with, there’s a candidate who has been on the other side of that desk. Sometimes candidates ask us odd questions and sometimes as jobseekers ourselves, we find ourselves in the hot seat, just like Jonathan Kestenbaum(@JKenstenbaum), executive director of Talent Tech Labs:

“I once had an interviewer put a math problem on the whiteboard right when I sat down. He didn’t say anything about it to me so I brushed it off. At the end of the interview, he asked me the answer to the math problem. I looked at him and asked for five minutes to answer the problem.”

Wow, tough task! Asking for a little time seems fair, but like life, some interviews just are not fair. Companies like Google and Facebook have long been known to stump their interviewees with puzzles and riddles, but Dyson (yes the vacuum company) have gone next level with puzzles you have to unlock to even GET to the interview. The British company got rid of the typical application and makes potential applicants solve a series of puzzles across the internet, beginning with a brainteaser video.

Interestingly enough, that might be even easier than the task Kestenbaum was given. His result after asking for a minute or two to solve the math problem?

“He said the guy who I need for this job should have been thinking through that answer throughout the interview,” said Kestenbaum. “Let’s just say I didn’t get the job.” You can research some commonly used hiring practices, including puzzles on this Quora string if that’s the sort of thing you’re into.

An Odd Duck of a Question

Of course, interviewing for a marketing gig will ALWAYS take the cake when it comes to strange interview questions. Liz Bardetti, VP of Marketing for Cybergrants, a corporate philanthropy software company headquartered in Boston, recalled a few interesting questions from her agency days.

“Would you rather fight one horse-sized duck or 100 duck-sized horses?”

What do you even say to that? How can there be a right answer to that question? How could that question possibly impact your ability to do a job? Oddball questions are the topic of a whole lot of articles in our space and rightfully so. When you spend most of your days interviewing people, we’re all liable to start asking duck-related questions at some point. But before you do, try some slightly more human interview questions on your (frightened) candidates.

Questions Concerning Being on Fire

Okay, I give. People are strange. Is the goal of interviews simply to scare the ever-loving heck out of people? If so, this question may take the cake.


Imagine yourself in a tunnel.

Out one side is a fire breathing dragon who will surely burn you to a crisp.

Out the other side is a blazing sun that will surely burn you to a crisp.

How do you get out of the tunnel?

Marc Wong, Chief Data Scientist at PeopleTicker, had to take on that wacky riddle at an interview. However, in this case, I might be able to see a point. Riddles and puzzles, unlike subjective duck questions, have the ability to test one’s logic and ability to solve thorny problems, which in the world of data science, is likely a very useful skill. Wong correctly answered the question and the rest, well the rest is compensation calculation history.


Wait until dark, and exit the tunnel on the side that had the blazing sun

If you need to test for logic, this isn’t a bad question. If you need to hire nice people, try these interview questions.

Penguins with Free Drink Tickets

Sometimes, there’s no telling why you’d need to answer any of these questions. Sara Pollock, head of marketing for ClearCompany, a Talent Management system for SMBs, has been asked more than her share of doozy questions. In fact, we probably could have done an entire article on the strange and befuddling interview questions she’s encountered.

How many high school students are there in the US? Walk us through your reasoning for that number.

You have two identical bowling balls and are in a hundred story building. The bowling balls will break when dropped from a certain floor. What is the smallest number of times you can drop a bowling ball to determine the highest floor the balls can safely be dropped from without breaking?

How many kegs of beer would Gillette go through if everyone in the stadium had a free drink ticket?

As a former candidate myself, I can tell you that if someone asked me any of those interview questions, I would likely walk straight out of the interview. Except the bowling ball one, I would ask to be immediately taken to the bowling ball room to check. But I DO know the answer to this one:

If a penguin wearing a sombrero walked into the room right now, what would he say?

Nothing obviously. Penguins cannot talk. In fact, they can barely walk. It’s more of a waddle.

The Interviewer Becomes the Interviewee

Michael Heller (@Michael_Heller), HR Pro and founder of iRevu, a performance feedback platform, is used to having the tables turned on him but it still makes him scratch his head a little:

“Having spent a good bit of time in recruiting, I have heard several strange interview questions, both from hiring managers AND candidates. I find it *very* strange when I’m being interviewed and get asked a question that has nothing to do with the job…”

‘How many golf balls would fit in this room?’

“I understand the interviewer was trying to sense how I solve problems, but I was being interviewed as a recruiter! I don’t believe I would ever need to do that as a recruiter unless I was part of some elaborate practical joke.”

What is that anyway? I am not even sure there is an answer that the interviewer would know them. Instead, and this is solid career advice, please learn to do this trick and you will get hired on the spot:

What’s Your Age Again?

As recruiters and hiring managers, we understand that we are NOT supposed to ask about certain things. Pregnancy, kids at home, marital status, and of course, AGE. But that doesn’t mean that candidates can’t ask us how old WE are. During an interview where she was the interviewer, she got, basically carded:

“So you’re a manager? How old are you?”

“I am a younger female in a sales world dominated by men, so this question really took me by surprise. I used this as a learning opportunity for the individual I was interviewing. I politely reminded them that for many reasons age should be avoided during interviews.”

From the balance:

Illegal interview questions, while not illegal in the strictest sense of the word, have so much potential to make your company liable in a discrimination lawsuit, that they might as well be illegal. These include any interview questions that are related to a candidate’s:

  • Age
  • Race, ethnicity, or color
  • Gender or sex
  • Country of national origin or birth place
  • Religion
  • Disability
  • Marital or family status or pregnancy

But Slack knew that and instead steered the question to her own advantage and decided to show off the culture of her employer.

“I also used this moment to discuss how the owners of Triage have created a culture where anyone can be successful if you are willing to put the hours and the hard work in,” said Slack.


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