People Share The Hardest Job Interview Question They’ve Ever Had To Answer And How They Handled It

Job interviews are the worst; mostly because of the anxiety leading up to them. You have no idea what they’re going to ask. If they ask expected questions, it’s a struggle to sound natural. If they pull questions out of left field, it’s hard to come up with a clever, appropriate response.

These netizens spill the beans about the absolute hardest job interview questions they’ve ever faced, along with how they responded. Some answers are inspiring, while others are, well, not so much. Perhaps the experiences of the latter folks can serve as lessons for all of us on what not to do in a job interview.

Don’t forget to check the comment section below the article for more interesting stories!

#38 Trick Question?

When I sat down, the very first thing the interviewer asked me was: “Do you know what time it is?”

My gut sank. Was I late or something? Did I mishear the interview time that the HR person told me over the phone?

I told him it was 1 p.m., which was the time the HR person told me to come in for.

He shuffled his papers and said, “Good, now we can get started.”

I guess he was just testing me or something.

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#37 Not A Trainwreck

I was asked by my interviewer how much money I made at my previous job. It wouldn’t have been so bad if the interviewer wasn’t someone I knew from high school. She wasn’t someone I was friends with back then, either. At that point, I expected the interview to be an absolute trainwreck.

I stayed professional and just told her the truth. “I made $40,000 a year.”

She smiled and said, “Don’t worry, I’m sure we can offer you much more than that!”

She turned out to be super sweet. I’ve been at the company for two years and we’re literally best friends at work now.

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#36 The Customer Is Always Right, Usually

Interviewer: “Is the customer always right?”

I had to think about this for a bit. I knew most businesses live by that rule, but realistically everything is on a case-by-case basis.

So I just said, “Usually, but not always. Depending on the situation, we also have to look out for the good of the business, as some customers will abuse that principle to get what they want unfairly.”

I got hired a few days later.

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#35 Reverse Psychology Didn’t Work This Time

Them: “Why shouldn’t we hire you?”

Me: “Because I care about my family more than my job, and if I have to choose between them and work, I’ll choose them.”


#34 Sit Down, Be Humble

I recently had an “email interview” before I had to attend a second, in-person interview. No big deal. It was a list of ten questions. I answered them, double-checked my work, and submitted them.

When I got to the in-person interview, the guy laughed at my “attention to detail,” saying that I had only answered half of the questions. I just sat there stupefied until I asked him if the rest of my email was on the back of his paper.

It was. He had printed it double-sided and not checked.

But the hardest part of answering was my stammering and trying not to call him out for his own mistake.


#33 Making It Without Even Faking It

About a year ago, I got called in for an interview at a company I applied to.

They started interviewing me with questions that seemed kind of strange. Questions like, “Can you tell us more about your event planning experience.”

I was thrown off. It eventually became clear that they were not asking me questions for the job I had applied for.

They were interviewing me for an event planning position, and I had applied for a job in tourism and marketing.

I finished the interview, shook hands and went on my way.

I ended up getting the job in event planning despite having little to no experience in the field.


#32 Shoes Matter More Than You Think

Interviewer: “So tell me, why did you choose to wear those shoes today?”

Me: “Um… what?”


#31 An Existential Interview

They asked me some pretty deep questions. It got to a point where they asked me why I was alive. Not in a “What’s your motivation in life” sort of way, but in a “Why do you exist, human?” sort of way.

Confused, I said, “You’re asking me why I’m alive?”

They took a short pause to realize where their follow-up questions took them and replied, “Yes.”

I’ve never had anyone question my existence during a job interview before.


#30 Learning From Past Mistakes Is Crucial

The question: “What have you learned in your current job?”

I was working a part-time customer service job for two and a half years. It was not in my field, and I HATE customer service.

My answer, with a smile on my face: “That I never want to do that again!”

Got the job.


#29 Unconventional Questions Require Unconventional Answers

Interviewer: “You’ve suddenly been shrunk down to the size of a quarter and dropped into a blender. It’s turning on in 10 seconds. What’s your plan?”

Me: “Sing in a high opera voice and shatter the blender’s glass, of course!”


#28 Commuting Is The Worst

“The only thing we foresee as an issue for you is the commute, which is just over an hour. How do you feel about it? We lost the previous person in your role because of a similar commute length.”

I had never commuted more than half an hour before, so I genuinely didn’t know. I said I didn’t think it would be an issue but genuinely couldn’t say for sure.

They offered me £4,000 more than the full amount advertised. My agency said they wanted to give me an incentive to take the role and cover the commute/drive cost.

I ended up moving closer to the office a month into the job. The commute drove me crazy, and I happened to need to move anyway.


#27 Be Prepared For Anything

I applied to an administrative job at an elite university on the East Coast and made it to the final round of the interview. It was just me and one other candidate, and we both met with one of the vice presidents.

The question itself wasn’t difficult, but the manner in which it was asked threw me off. The vice president essentially walked into the room, shook my hand, and before we even sat down, he asked me: “So, what can you do for me?”

I was expecting the first two minutes to be small talk, so I was caught completely off guard by the straightforwardness of the question. I mumbled out an answer, but I knew right away I didn’t impress. The interview only lasted another 15 minutes and needless to say I didn’t get the job.


#26 A Seriously Hands-On Interview

“The company is rolling out new customer rewards cards across the country, but they’re not sure if they will be profitable. In addition, certain provinces have regulations that restrict the use of selling these cards. Do you decide to launch it or not? What are the key considerations?”

I had to draw up some master plan with calculations in 30 minutes in front of them. It was one of those hypothetical case questions. I got the job.


#25 An Interview Gone Morbid Doesn’t Usually Sit Right

“One day your parents are going to die. After you bury them, you will never talk to them again. They’re gone forever. You will have to look in the mirror and ask yourself, ‘Was I a good son to my parents?’ Well, are you a good son?”

This was for a post-law school interview with a judge. I didn’t take that job.


#24 Pulling Out The Race Card

I got a combination question:

“You like black people? Ok, yeah, well, what’s the best flavor of Kool-Aid?”

Back story: The manager had forgotten about my interview and told the two guys working that night to interview and hire me.


#23 Pay Attention Or Pay The Price

It was a lunch interview, and at the end, the manager asked:

“Who was our server today?”

I had no idea because I was more focused on hearing the specials than her name. Must have made me look like a snob though because I didn’t get the job.


#22 Are You Messing With Me?

It wasn’t so much a question as it was a situation. I attended a round of interviews right before graduating from college. The company flew me and two of my classmates out. They put us each in different rooms and we interviewed with several departmental heads from the company.

The interviews were pretty standard. I could tell they were trying to see who would fit best into their company culture, as well as perform the job well. We were all qualified, so it came down to personality.

Everything was standard until the third manager that interviewed me. He came in, shook my hand, and sat down. Average height, maybe 220 pounds. He had thick, oily hair, cropped neatly on top of his head. He had an odd posture, kind of holding his head back, the way anyone would do when trying to give themselves a second chin, pushing his jaw down into his neck a bit. I remember every detail about this guy because of the interview.

He began talking to me a bit, but then it happened.


In the middle of his sentence, he straight up just made a fart noise by sticking his tongue out of his mouth, closing his lips and blowing. It was quick, but it caught me completely off guard. He went right back into what he was saying.

He only did it once before finishing what he was saying, and I started to answer. However, as soon as he stopped talking and started listening, I began to get assaulted by loud, longer, face-like-a pufferfish, fart noises. It was clear he was trying to suppress it, but that it was very hard.

I thought this guy had Tourettes. Either he had Tourettes, or he was messing with me on a major level.

Whenever he spoke, it was less. Less often, less intense. But whenever I was talking, I could tell he was trying to listen intently, but he couldn’t contain himself nearly as well.

The interview went on and eventually finished. I was stone-faced. I made it through two more rounds and they took us for lunch. He continued to do it occasionally there, with the rest of his coworkers. None of them reacted, so I felt affirmed that it must be Tourette’s.

After a long day, they took my classmates and me back to the airport. As soon as we got through security, we all completely broke out into laughter.

We had all come to the same conclusion, but to this day I don’t know if it was some kind of interview tactic or not. I’ll never know.


#21 Takes One To Know One

I applied for a security job and was asked: “What do you think makes you qualified for this job?”

I replied, “I’ve been stealing things for years, and I have yet to get caught. I know all the tricks.”

Got the job and made a great friend.


#20 Sick Children Trump Deadlines

“If you had an important deadline and your child was also very sick, which would you attend to first? Come into work for the deadline or tend to your child?”

I almost did not take the job once they offered it to me because this question bothered me.


#19 Give It Your All Or Go Home

“Would you rather focus on one thing and do it 100% well while doing two other things poorly, or would you rather do three things at 70%?”

It was a tough question.

I told them off the bat that I give 100% in my projects and I hate presenting things that I don’t feel are up to my standards.

#18 Previous Work Experience: World of Warcraft

I was 15, and the manager at the A&W asked me about my previous work experience.

My response: “Uh, I manage our healers and loot distribution in our World of Warcraft raiding guild…”


#17 The Depth Of Knowledge Is Hard To Measure

For a software developer job with a minimum of five years experience I got asked, “Out of 10, how would you rate your net knowledge?”

I answered, “About 6 out of 10.”

He looked at me very puzzled and said, “We just had a guy in here straight out of university, and he’s rated himself 9 out of 10.”

I replied, “He’s not even aware of the things he doesn’t know about. Net is huge. If I were 9 out of 10, I wouldn’t be here.”

He had a developer in the room, and he looked at him like I’d just spat on his kids.


#16 If It Ain’t Broke, Don’t Fix it

I got asked to sell the interviewer a pen that she pulled out of her pocket. I had watched The Wolf of Wall Street three times already, so I pretty much just re-enacted the scene. Still got the job.


#15 Always Let Your Conscience Be Your Guide

I was interviewing to work at a treatment center for youth recovering from addiction and eating disorders.

Question: “If we asked you to do something you felt was morally wrong, would you trust that we are more skilled and understand the situation better and do it anyway?”

Answer: “I don’t think I could, in good conscience, do something I felt was wrong regardless of the situation.”

I didn’t get the job. They were shut down a year later.


#14 Outside The Box Is Better Than In

I interviewed with a comic book company. The interview went incredibly well, and the last question they asked was, “Who is your favorite hero?” To this day I regret not saying, “Agent Phil Coulson.” I went with Spiderman because there was a giant Spiderman mural on the wall next to us.

I don’t work there full-time, but they did hire me out as a freelancer from time to time which was cool.


#13 This Job Interview Was The Bee’s Knees

I was applying for a sales position at a major firearms retail store. The application asked for my hobbies. I listed hiking, kayaking, fishing, and beekeeping.

At the end of the interview, my now-manager read over my application. I saw his eyebrow go up and he said, “Under hobbies, you listed beekeeping. Tell me about beekeeping.” Another manager, the regional manager, and the corporate director of operations were also in the room. I saw all of their eyes simultaneously snap up from their notes and focus on me. Suddenly, after a great interview, I was the weird little beekeeper in a small, hot room.

So I told them about bees and keeping them. I had their rapt attention, telling them lots of cool stuff about bees. I closed with, “So if I get this job, then a few times a year I’ll bring in jars of honey for my favorite managers.” If you can keep your cool in a sweaty beekeeper’s suit while thousands of bees are trying to sting your face, a job interview is a breeze.


#12 Why Would You Not Want This Job?

A question that sort of took me by surprise at the end of the interview was something along the lines of, “What reasons would make you refuse the position if you got the job?” I was flustered and hesitated many times. I ended up saying something cringey like, “I tend to give new opportunities one chance. Either way, it will be a learning experience.” I got the job and have been working there for nine months now.

#11 Hiring For The Position Of “Bro.”

I had progressed to the final round of interviews, and it was the boss’s task to interview the final candidates. The first question he asked was how many beers I could handle. It was an interview for an office job, and the question had zero relevance to the position or industry. I wanted the job, but it was clear that the guy had zero interest in the whole interview process. I just replied that he’d have to wait until the office Christmas party to find out. I got the job.


#10 Smashing The Question Out Of The Park

I applied for a management role at my first job when I didn’t have any management experience and got knocked back.

The person they hired failed miserably, and I went for it again about three months later.

They asked me, “So, you applied three months ago, and you got turned down. Why do you think you’ll get it this time?”

I answered, “This is still my first job. Without leaving and becoming a manager elsewhere, I still have not been a manager. What I’ve done instead is taken every opportunity to gain the relevant traits you’re looking for. I volunteered to coach the group of new starters we had. I took customer escalations where they’ve asked to speak to a manager and resolved them myself. I’ve made myself a presence in the office so that if there is an issue and there isn’t a manager around, staff can come to me for help or advice. I’m doing small parts of a manager’s role every day.”

I got the job. In my feedback, they said it was between me and someone else, and it was incredibly close, but I got the job based on that answer, so I’m pretty proud of myself.


#9 Who Needs A Boss When You Can Evaluate Yourself?

I was asked if I’d rather do my own annual “self-evaluation,” including a list of goals and objectives for the forthcoming year, or have a department head fulfill this role.

I opted for the self-evaluation, stating that I’m my own worst critic. That worked well for the interviewer as it displayed my determination and ability to work independently.


#8 Physics, Marketing, What’s The Difference Anyway?

Recently, I was asked, “If you could have dinner with any deceased person who would it be?” I was unprepared and blurted out, “Nikoli Tesla,” then went on a three-minute tangent about how Edison screwed him over. The job had nothing to do with physics; it was marketing.


#7 Back To Basic Math

I was interviewing for an analyst position at a bank. During the interview, the guy was friendly, and we were talking about all sorts of casual stuff, like my upbringing, my family, etc.

Then out of nowhere his expression became all serious, and then he asked me, “If an analog clock shows 3:30 right now, what is the angle between the minute hand and the hour hand? You have 30 seconds.” He then pulled out a timer that beeped every second as it counted down to 0.

It took me about 10 seconds to grasp he wasn’t joking, then another 10 seconds to try to collect myself, which left only 10 seconds to solve the problem. I failed.


#6 The Question Bites Back

It was a brand new position at a company. The interviewers had zero knowledge of the type of work this new position would entail. When they asked me if I had any questions for them at the end of the interview, I asked, “What goals do you see being reached by adding this position?” And their reply was, “Actually; we’d like you to answer that.”

I couldn’t help but laugh. This is your position and company, not mine.


#5 Word Play For The Win

When you apply for a business school after the high school degree in France, you have to pass written exams and an oral exam. The orals are well-known to have tricky questions, and my friend was asked this: “Êtes-Vous vierge?” (Are you virgin?) They ask this to see how you handle tough moments of instant stress.

My friend hesitated a bit and then replied, “Well, actually I’m a Leo.” (In French, “Virgo” and “virgin” are the same word: vierge.)

That answer is still one of the most epic answers the exam guy must have heard. Both a wordplay and a valid answer. He, of course, did pass the exam and attended the school.


#4 A Little Speeding Never Hurt Anyone

Interviewer: “Do you speed?”

Me: “Yes, usually five miles per hour over the limit.”

I’m now the operations manager.


#3 Creativity Is The Name Of The Game

“Name 15 different things you can do with a brick.”

Pretty tough when you are on the spot.


#2 Don’t Look Back

I attended an interview for a retail job. The guy there asked me what I would redo if I could start my life over. I handled it by leaving and never going back.


#1 Wrong Answer Buddy

I applied for a job as a radio DJ. One of the questions was to pick which new releases would die fast or stay around a long time. I picked Hozier’s song “Take Me To Church” as a song that would die quick.

I did not get the job, and I still hear Hozier on the radio.