25 Interview Questions That Made Candidates Pause, Reflect, And Share Online

Published 4 months ago

Job interviews can be nerve-wracking experiences, and often, it’s the unexpected questions that catch candidates off guard. A recent Reddit thread brought together job seekers from various industries to share their encounters with tricky interview questions that linger in their minds.

From the bizarre to the thought-provoking, these questions serve as a reminder of the unpredictable nature of the hiring process. Let’s delve into some such tricky job interview questions that have left a lasting impact on candidates.

More info: Reddit

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Image source: ap1msch, LinkedIn Sales Solutions

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 source: ManyAreMyNames, DS stories

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 source: Iron_73, Kahyap Pictures

“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 source: SweetCosmicPope, Christina @ wocintechchat.com

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 source: ravikrn, Christina @ wocintechchat.com

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 source: Cheese_Pancakes, James Yarema

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 source: PunchBeard, RDNE Stock project

“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 source: Soul_of_Sorrow556, Mimi Thian

“Tell me about yourself”. I immediately forget everything about myself


Image source: tukk_vuly, Daiga Ellaby

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 source: hugesteamingpile, Warner Bros. Pictures

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 source: originalchaosinabox, Tima Miroshnichenko

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 source: kgbjay, Antoine Dautry

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 source: ATXKLIPHURD, Jeremy

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 source: uribelfi, cottonbro studio

Where will you be standing at the office holiday party?


Image source: Ligmartian, Magnet.me

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


Image source: PlayfulPrincesXO, Rilla Paris

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.


“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.

Image source: Pumpingions


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.

Image source: btk12


Image source: Tanky50, DLKR

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!


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.

Image source: nikolacarr


Image source: MistakeMysterious347, JESHOOTS.COM

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


Image source: praizeDaSun, Sebastian Herrmann

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.


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

Image source: Wind5urfer


Image source: owlman17, Sippakorn Yamkasikorn

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


Image source: Th4t9uy, Becky Phan

“What role would you be in a circus?”

Saumya Ratan

Saumya is an explorer of all things beautiful, quirky, and heartwarming. With her knack for art, design, photography, fun trivia, and internet humor, she takes you on a journey through the lighter side of pop culture.

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interview questions, job, job interview, job interview questions, job interviews
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