40 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online

Most of us probably are not the biggest fans of job interviews. We always want to answer all the questions as best as possible, show our best qualities and finally - in most cases, get the job. However, we tend to worry, forget what we planned or wanted to say and if we get some extraordinary questions that we were not ready to get asked, well, that may mess everything up.

One Reddit user created a thread online asking folks to share the trickiest or hardest questions that they have heard during a job interview, and probably a few of them would confuse almost all of us. Scroll through them and share your opinion!

More info: Reddit


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."

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.

Image credits: ManyAreMyNames


“Why should I hire you over a fresh off the boat immigrant that will do everything you do for a third of the pay ?”

I responded because “I believe a company that pays its employees fairly shows integrity of management and reflects well on the company as a whole.”

I didn’t get the job

Image credits: Iron_73

Bored Panda got in touch with Margaret Buj, who is an expert interview coach and career strategist. She kindly agreed to share her professional insights regarding this topic!

To begin with, Margaret noted that unusual or unconventional questions in job interviews serve multiple purposes. “Firstly, they can help to gauge a candidate's creativity, adaptability, and ability to think on their feet. These questions often require candidates to approach problems from unique perspectives, showcasing their problem-solving skills beyond the standard behavioral questions.


"Can you tell me about a time where you experienced a lot of stress on the job? And how did you handle it"?

I'm an Iraq War veteran who served as a combat medic with the infantry when I was in my early 30s. If you want me to go into more detail I can but you probably wouldn't believe it.

Image credits: PunchBeard


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."

Image credits: ap1msch

She added that unusual interview questions can reveal a candidate's personality traits and cultural fit within the organization, as their responses offer a glimpse into their thought processes and values.

“Personally, I am not a fan of asking very unconventional questions but I believe the interview should be a conversation where you not only ask some standard general and competency-based questions but you also get to know them as a person,” she noted.


"Tell me about yourself". I immediately forget everything about myself

Image credits: Soul_of_Sorrow556


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?”

Image credits: originalchaosinabox

Now, we asked Margaret if there are some interview questions that should be avoided and she pointed out that questions which delve into personal or sensitive topics unrelated to the job can be inappropriate and potentially discriminatory. 

“Additionally, questions that are overly abstract or unrelated to the role may not provide meaningful information about the candidate's qualifications or suitability for the position,” she emphasized. “It's important to ensure that all interview questions are relevant, fair, and respectful of the candidate's privacy.”


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:


They said it like:

What is 2 times 5? Waited for an answer... Now add 5. Waited for an answer... Now divide by 3. Waited for an answer. Now add 8. 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...

Image credits: kgbjay


I was going for my first job change as I was sick of working in fast food and thought a liquor store would be a good option. In the interview I was asked to tell a story and the interviewer said: "It doesn't have to be related to the job or anything, just tell me a story that you find interesting".

That is NOT something I prepared for in the slightest.

Image credits: PlayfulPrincesXO


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 details about why I liked that feature so much and what really draws 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. 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 7 years now and I've never applied again and I find it hilarious they can't keep people staffed.

Image credits: SweetCosmicPope

Finally, Margaret pointed out that unusual interview questions play a significant role in assessing a candidate's skills beyond the standard qualifications listed on their resume. 

“These questions can assess a candidate's critical thinking abilities, problem-solving skills, creativity, and cultural fit within the organization. By presenting candidates with unexpected challenges, interviewers can observe how they approach unfamiliar situations, communicate their thought processes, and adapt to new scenarios.”

“So while unusual interview questions can be valuable tools for assessing candidates, it's essential to use them thoughtfully and in conjunction with more traditional interview techniques to ensure a fair and comprehensive evaluation process,” she noted.


Not in-person, but recently applied for an entry-level zookeepers position.

The zoo had a *very* long online application process, which included these three questions:

- Do you have experience dealing with intense, persistent, and varied unpleasant odors, in the workplace or while volunteering, and continuing to complete your assigned tasks in spite of them? If so, give examples

- On a scale of 1-10, how confident are you in your ability to deal with even the worst animal odors without interruption to your assigned tasks? (**Caution** - those who answer with a high number may be required to demonstrate this ability in their practical interview).


Sounded kind of ominous. I'm just a recently college grad but I just talked about my experience volunteering at a farm and a doggy day care, and put "10" for the second answer, but I'm not sure if that's what they wanted or not.

I did get called for a practical interview next week, so...hopefully that goes well?

Image credits: tukk_vuly


It was a pretty stupid one, but it was when I was interviewing to be a server at a restaurant while I was in college. The proprietor asked me all of the standard questions you'd expect, then said "Sell me a coke".

I get that he wanted to see my ability to sell things to the customer, but a coke was a hard one for me. Seemed to me like a non-alcoholic beverage is not normally something you'd have to talk a customer into - it's something they'd already know they wanted or not. I would have had an easier time if he wanted me to upsell him on a side dish or dessert. Bumbled my way through it by talking about how refreshing an ice cold coke would be with his steak.

Luckily it got the proprietor laughing and he liked me enough to hire me. Hated that question though and I felt like an idiot trying to do it.

Image credits: Cheese_Pancakes

Of course, don’t forget to check out Margaret’s website where you can find a useful information how to get hired, promoted and earn more!

So guys, what is the trickiest question that you have heard during a job interview? Share your thoughts below!


Interviewer: Lets 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, proceeds to ask tough questions)

Interviewer: Good, now answer these questions

(I was shaking during the interview)

Image credits: ravikrn


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 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 and walk into the sunlight and feel its warmth immediately.

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

Image credits: hugesteamingpile


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.

Didn't get that role, but he recommended me for a different one!

Image credits: Tanky50


A friend of mine was asked to solve riddles. He's a programmer.

Image credits: MistakeMysterious347


My boss uses “why is a tennis ball fuzzy” to gauge what type of thinker the person is. He sat on an interview panel for a position I was hiring for and the various answers were amazing.


"what type of music do you think your work style is most like"

I was completely taken by surprise, so in a moment of panic I said ska and had to awkwardly try to justify why my work style is like a ska song.


Would you still interview with us if I was a worm?

Image credits: owlman17


“Teach me something new in less than 120 seconds” *starts timer*


Asked me if I would rather wrong a co worker or a client and there was no wrong answer. I thought about for a minute and explained why I would choose client because a co worker I would still need to work with everyday and clients come and go. The younger of the 2 managers she looked at me like wtf! The older gentleman asked if I could start next week. 10 years later still with the same company and she was demoted 3 months later and then quit. Had no business being there in the first place.

Image credits: praizeDaSun


"What role would you be in a circus?"

Image credits: Th4t9uy


I had a pretty rigorous interview for a legal role (I got the job and was promoted - still here). I like to shoot the s**t and ask people about their hobbies and come off as a pretty personable and knowledgeable person.

However, I was asked whether I was an animal person.

I was facing a conundrum - I am a cat person. I like dogs (in theory) but have never had one. I was worried if I said I was a cat person the dog people on the panel wouldn't hire me. If I said "oh yeah I like animals" or "yeah I like dogs" they might think I'm bulls**tting. I ended up telling the truth and now I am the lone cat person in an office full of dog people.

It scares me that this might have been the determining factor in their hiring decision lol.


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."

Image credits: mattsylvanian


Had a hospitality job question once:

I'm the host at a bar/restaurant. In walks, at exactly the same time, a regular and 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 regular customer. But at the moment, I blanked.

Image credits: festertheinvester


"In the 1980s, AT&T had a set of payphones in Grand Central Terminal train station in New York City. They had a problem where they were getting complaints that the lines for the payphones were getting too long, because people were spending too much time hogging the phones.

AT&T came up with a solution to reduce the problem and make the lines shorter; what do you think it was? Note: the answer cannot be to add more phones to the phone bank, and it cannot be something overly expensive."

Allegedly, this was based on a real problem AT&T had to solve in the 80s, though I can't find any proof of it off-hand. They explained that the idea was to see if interviewees could problem-solve creatively. They liked the solution I proposed (make the train announcements louder, so that it would be harder for people to have long & unnecessary phone conversations), though according to them, the solution IRL was to >!make the phone handsets weigh more, so people's hands got tired of holding them for long stretches!<.

^(EDIT: Also, just for clarity's sake, this job interview was not with AT&T, so don't take this as an insider scoop on their hiring process.)

Image credits: blueeyesredlipstick


My friend was being interviewed to get into Med. After a grueling hour of rapid-fire questions from various interviews, his heart is racing, and they tell him this is the last question. The pressure rises.

"What's your favorite fruit! Why?" He wanted to say banana because he has one with breakfast all the time, but then felt it was too phallic and freaked. Ended up saying "grapes" because "they're juicy and refreshing." LOL. He was embarrassed. They started mocking him for giving a stupid answer, asking if he was sure that was it. He wanted to cry. He was so fed up, tired from the get-go being a student with a part-time job AND a volunteering position, working like 60-70 hours a week. The adrenaline was crashing.

But he kept it together just long enough (tears came later), and he passed! They basically roast people to see how they handle stress and confrontation.

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Where will you be standing at the office holiday party?

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"Tell me about your best friend."

It seems that this question would gauge a few things: (1) who you are, as you are who you hang out with, and (2) how you talk about other people.

Image credits: Waltgrace83


"Did you make your bed this morning?"

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If you were a hiring manager and had 2 candidates for the same job. 1 is very young with no experience and the other is older with 20 years experience. Which one do you hire? I answered the older one. Nope! The answer was younger guy because they work for less money and you can train them how you want the company to run.

Image credits: ATXKLIPHURD


My most recent boss threw me the curveball of “what do you think of the word ‘should’”?

Image credits: Ligmartian


I applied for a promotion, and my supervisor was really adamant that I was unqualified for it. Anyway, at one point she asked me "How would you make sure the people under you will trust you?"

I was so baffled, because like, the job was really just calling instructors to ask if they were available for certain classes. I was just thinking, why the hell do they need to "trust" me?!? And I said something awkward about how the question threw me off and I didn't have a good answer.

She rolled her eyes at me and said, "I find that interesting, because, you see for me, you'll notice that the instructors all consider me to be a friend." Like, ok, that's nice?

Image credits: heidismiles


I had a interviewer once ask me what do you do if you're in the elevator with a stranger. I'm a huge introvert so I said just wait for my stop. The elevator isnt really a place to strike up a conversation. He asked me to try again and I said maybe compliment something about the other person and he likes that answer. It wasn't for a customer service role so I don't know why he asked it.


What was the most unexpected compliment someone gave you and why?


Not a requirement or on job description: ‘How are you with Microsoft Excel?’

Image credits: Dr_Stef


''If you were the one conducting the interview, what question you would have asked me?''

That was a bit of a curve ball for me because I didn't manage to understand the intentions behind it at that moment, so I just went:

''Do you have any vices?''

Followed by a 20 minutes b******t explanation on why is relevant to fully know the person you're intending to hire, because if today I'm doing something that could end up damaging my business, tomorrow I can do the same for you.

This was an Executive Assistant interview.

Image credits: piquerto


I ask this, “you can only choose one - what’s more important, process or outcome?”


What activities and efforts do you work on daily to help improve your organization’s DEI standing/investment?

I paused, and answered realistically.

“I presently work for a company with 300 employees, of which 293 are men, 7 are women, where sexism and racism are rampant. Efforts to call out those practicing either have been swept under the table from everyone from my immediate supervisor to HR to the company owner.”

One employee even went as far as to advocate for working on MLK day because “he’d never celebrate a n-word”

“So I desperately want to be a part of a workplace that embraces the true buildup of the surrounding community, not an echo chamber of deeply disturbing hatred fueled by a homogenous white conservative workplace.”


“How have you turned a problem into an opportunity?”

I had no answer. I didn’t get the job. Then later after the person they went with flaked out they called me again and I got the job. I work in procurement in ecommerce and every single day it’s turning problems into opportunities. It’s been an amazing lesson and I feel fortunate I was at least their second choice.

Image credits: MeanOneGrinch


Back in 2011, I interviewed for a marketing position and was given a riddle to solve after my first in-person interview with my would-be boss. Now, I just don't have a brain to do riddles quickly. I'm just not wired that way and this riddle stumped me. I tried Googling it and found nothing.

That is, until I Googled a less specific phrase (I think it was "This process continues until a proposal succeeds") and found that the riddle was actually The Pirate Game.

So, I whipped up three pages of explanations with illustrations and sent if off. Soon, I was told that I solved the riddle and would be meeting with the CEO.

A few days later, I meet with the CEO and he's got a print out of the goddamn riddle. He spent the interview asking me about the goddamn riddle and, obviously, I did not get the job.

So, despite me figuring out the riddle and finding the correct answer, I was not offered the marketing position.

Image credits: ElCoolAero