The Trickiest Questions People Have Been Asked In A Job Interview

We should all be able to agree that the job-hunting scene is tough, and landing an interview is already a big enough hurdle on its own.

But when you walk into an interview that's riddled with puzzles and trick questions, it can feel downright demoralizing.

After all, you went there wanting to talk about all that you imagine yourself contributing to the company and what this job would mean to you, and they'd rather hear about how you'd categorize their spices in the back room.

Redditor Flashy-Amoeba-7827 asked:

"What has been the hardest or trickiest question you've heard at a job interview?"

Doing The Work For Them

"Interviewer: 'Let's swap roles. Take this resume (my resume) and assume you have to interview me. Make sure you ask tough questions.'"

"Me: (As I know my weak points, I proceeded to ask tough questions.)"

"Interviewer: 'Good, now answer those questions.'"

"(I was shaking during the interview.)"

- ravikrn

That's Not How That Works

"I don't think this was a good question, but it obviously was a question they were trying to trick you with. I guess? I think they were just stupid."

"The interviewer had an equation in their hand but didn't show me it, that looked like this: 2(5+5)/3+8-3"

"They said it like:"

"What is 2 times 5? They waited for an answer... Now add 5. They waited for an answer... Now divide by 3. They waited for an answer. Now add 8. They waited for an answer. Now subtract 3."

"So naturally I went, 10... 15... 5... 13... 10..."

"They say I'm wrong."

"I go, 'Oh? Can I see the question?'"

"They show me the equation, and I'm like, you didn't read that properly. You told me that like a series of steps, not an equation."

"They said I should have known what they were saying if I knew BEDMAS."

"Ok... sure, it's me..."

- kgbjay

Handy Trivia Skills

"I recently had an interviewer ask me why manhole covers are round. He framed it as a critical thinking question, but he wasn't prepared for me to know the actual answer, let alone answer nearly immediately."

"I managed to turn it around and convince him that my random knowledge is earned through the preparation I've done over the years for various projects."

"I didn't get that role, but he recommended me for a different one!"

- Tanky50

Brutal Honesty For the Win

"Interviewer: Why did you choose this place of employment for work?"

"Me (being the brutally honest person I am): Umm, because you guys are hiring and I have bills coming."

"That made the guy chuckle at my response, which he responded to me with, 'Yeah, h**l buddy, don’t we all?!'"

"He said he didn’t have any more questions, stood up shook my hand, thanked me for my time, and said he’ll see if he can get some bill money coming my way."

"I got a call the next day. I got the job."

- buttrnURbread

...Same

"'Tell me about yourself.'"

"I immediately forget everything about myself."

- Soul_Of_Sorrow556

That Feels Incredibly Sneaky

"Not sure this counts as a question, but was tricky none-the-less."

"I live in the Bible Belt (Mississippi specifically) and while it's not illegal to ask what your religion is or what church you go to, it is illegal to not hire someone because of their answer. So naturally, people just avoid this line of questioning altogether."

"Anyway, I was invited to a lunch interview and when the food came the two people from the potential employer didn't eat and kept talking. I thought it was strange after about five minutes, so I started eating, and they IMMEDIATELY looked at each other and asked who was going to say the blessing."

"They were waiting to see if I prayed before I ate and could therefore find out if I was religious without asking."

"I thought it was pretty clever, to be honest."

"But I'm not interested in working for someone that my religion is that important to."

- Sir_Atlass

Set Up to Fail, Maybe

"I ask candidates, 'You are asked to do something that you are certain will fail. How do you proceed?'"

"Some people say they do it because they were told to do it. Some will say they will do their best not to fail. Some will refuse to do something they know will fail. Some will say that they will escalate/complain about the unreasonable request."

"There is no single right answer, but the conversation is important. The best candidates ask questions, like 'How do I know it will fail?' or 'Do I have alternative approaches that would work?' or 'Am I being asked to do the thing, or am I being asked not to fail?' Asking questions is important, and getting context is important before answering."

"The best answer I ever got was, 'I'd want to understand what I'm being contracted to do. If it's to do the failing thing, then I'd revisit the request for clarification that what was asked is the intention. If it's to do something, and the approach is the thing that will fail, then I'd suggest an alternative approach. If the customer is insisting on doing the thing that I know will fail, I'd clarify that with the customer, get it in writing, and then I'd highlight the risks of proceeding. I'd then proceed, and you never know... I could have been wrong... but I'd have gone about it the right way to mitigate risks.'"

- ap1msch

The Complexities of Orange

"I was interviewing as a graphic designer for a company that produced ads for cars that would go on Facebook, newspapers, banners at airports, and the like. The interviewer went over the regular sort of graphic designer questions, we went over past work that I had done and I thought I had done pretty well."

"Then I was taken to another office and sat with a woman who only asked me: 'How would you describe the color orange to a blind person?'"

"I remember stumbling for an answer while thinking of the Voight-Kampf test from 'Blade Runner.' I think I finally said something about how it feels when you go outside on a frosty morning, walk into the sunlight, and feel its warmth immediately."

"I ended up not getting the job. Pretty sure I’m not a replicant in any case."

- hugesteamingpile

Life's Most Demanding Questions

"The trickiest I've been asked: 'Do you tend to follow your heart or your brain more?'"

"This was for a children's theatre, and both answers seemed simultaneously to be good and bad responses."

"I've never been asked this, but I actually kind of like it for the variety of ways a candidate can choose to answer: 'Describe step by step how you would make a peanut butter and jelly sandwich.'"

- mattsylvanian

So Clever!

"A friend of mine applied for a job in sales, about which he didn't know anything but he has the gift of gab. Interview went like this:"

"Interviewer points at a thing on his desk: 'Sell me that.'"

"My friend: 'I don't know what that is.'"

"Interviewer: 'It's a dictaphone.' (This was many years ago.)"

"My friend: 'What's that?'"

"Interviewer: 'I use it to record letters and memos and then have the secretaries type them up.'"

"My friend: 'Oh, is that what I saw them doing with the headphones? How do they type and work the machine?'"

"Interviewer: 'They use foot pedals for play and rewind and so on.'"

"My friend: 'Well, that's really clever. How much does a thing like that cost?'"

"Interviewer: 'This one's about 500 dollars.'"

"My friend: 'You'd pay 500 for one of those?'"

"Interviewer: 'Sure.'"

"My friend: 'Sold!'"

"Interviewer stops cold. Stares at my friend for a few seconds. Leans back in his chair. 'Son of a b***h.'"

"My friend got the job. Had a fabulous career in sales, retired a couple years ago."

- ManyAreMyNames

Real Talk

"For a cashiering job at Target, I was asked why I wanted to work there. I was about 21."

"Turns out 'I really like the store and the variety of products you sell' is not good enough, because the dude called me out."

"Sir, this is the lowest level job you have. What kind of answer do you expect? I mostly want money."

- kittenplusboop

Stacking Up That Experience

"I’ve worked in small towns all my life. Been trying for years to get a job in the city. My last interview for a job in the city hit me with this one: 'So why do you think you’ve never been good enough to get out of the small towns?'"

"He did not like my answer: 'Well, your rejection letters always say you’re looking for applicants with more experience. So I’m out here getting more experience. Do I have enough yet?'"

- originalchaosinabox

The Turnover Rate Is Telling

"This was the worst interview I ever had. So I was doing a phone interview with two IT managers at a company called Apptio. So I'm doing pretty well on the technical portion. I'm quite good at my job."

"But then they interrupt and say, 'What is your favorite feature of our product?' Bear in mind that I'm an IT guy. I'm not a software developer. I was going for a sysadmin role at the company, working on infrastructure projects and end-user devices and systems."

"I had done my research so I just named one of the features I could remember. They wanted me to go into detail about why I liked that feature so much and what really drew me to it."

"When I explained that I don't really have any experience with their product, the interview mood did a complete 180. Now all of a sudden, I was being interrogated about why I hadn't used their product, and why I was even bothering applying to their company if I've never used it before."

"And these guys began getting super rude and annoyed with me. I ended up telling them that I didn't think this was going to be a good fit and hung up on them."

"A few years later, I was mass-applying after a layoff and applied again. The same two guys, and the same exact conversation happened. I've seen that job rotating onto the job boards off and on for at least seven years now and I've never applied again and I find it hilarious they can't keep people staffed."

- SweetCosmicPope

So Many Ways to Approach This

"I had a hospitality job question once: I'm the host at a bar/restaurant. In walks, at exactly the same time, a regular, and a well-dressed newcomer. Who do I seat first?"

"I totally blanked, because the question is set up to essentially be equal, just what do you value more: showing the regular he's valued or potentially making a good impression on a (potentially) new customer?"

"Looking back, I'd choose 'new guy' because I could always comp a drink or dessert for the regular customer. But at that moment, I blanked."

- festertheinvester

I... What?

"Straight-faced, he asked me, 'Would you still interview with us if I was a worm?'"

- owlman17

Honestly, job-hunting is already tough enough and high-pressure enough with all the tricks mid-interview.

The question we always have is, are answering these questions really all that telling about how a person will participate in a particular job? Or are we just checking to see who we can invite to our monthly Trivia Night?