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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

#1

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

ManyAreMyNames , DS stories Report

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#2

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

Iron_73 , Kahyap Pictures Report

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.

#3

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online "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.

PunchBeard , RDNE Stock project Report

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LaserBrain
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I once worked with a guy who used to be a combat medic. He had a T-shirt that said "My job is to save your a*s. Not to kiss it." I kind of liked that.

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#4

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online 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 , LinkedIn Sales Solutions Report

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HolyDiver
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

If your trying to fail and you succeed, have you failed or succeeded?

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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.

#5

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online "Tell me about yourself". I immediately forget everything about myself

Soul_of_Sorrow556 , Mimi Thian Report

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WindySwede
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

"Well, some 4 billion years ago there was the first of my ancestor, and now I need to go to the office. Hired?"

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#6

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online 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? 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...

kgbjay , Antoine Dautry Report

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Tucker Cahooter
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I didn't hear any brackets being mentioned. Probably the idiot interviewer was just given the question to ask by someone else

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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.”

#7

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online 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 , Tima Miroshnichenko Report

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Lotekguy
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

It won't help your finances, but I think your answer was excellent. Apparently, they weren't looking for people with a functioning backbone.

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#8

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

SweetCosmicPope , Christina @ wocintechchat.com Report

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Trophy Husband
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I interviewed for a job once and my resume listed a technology I had manager, but only on occasion. Apparently it was the main thing they liked about my experience and they asked a number of questions about it. Unfortunately, I didn't remember the actual names for the parts of the interface. So while I could have passed a practical test (i.e. here's a system, fix this problem), I didn't know what about it it was called and they thought I had lied about my experience. I went back to my job and opened that program up and looked at the main screen, I had said that I didn't know how get to the first screen because I got confused about what it was called. They probably still joke about the guy who lied on his resume. Meanwhile, I would have rocked that job without trying.

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#9

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

PlayfulPrincesXO , Rilla Paris Report

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Adam Belaire
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I recall the story of Old McDonald, who apparently had a farm, called EIEIO. As he was a farmer, he had several animals. On this farm, he had a pig named EIEIO...

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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.

And 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!

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#10

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

tukk_vuly , Daiga Ellaby Report

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Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Someone who runs a monkey sanctuary cheerfully said in an short documentary: "I used to design handbags, now I clean up monkey poop!" That's a great attitude. Not-so-good attitude: a self-proclaimed dog-lover who offered to walk a dog - but said "forget it" when handed a poop bag. I'm glad they didn't have kids!

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#11

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

ravikrn , Christina @ wocintechchat.com Report

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Hey!
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

I had a friend who would ask her children what would be the appropriate punishment. Seems the same to me. I don't like either.

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Additionally, we got in touch with Connie J. Clace, CPC, a professional career coach, and she kindly agreed to share her insights regarding interview questions.

“Interview questions, whether they are unconventional or not, should only be asked if they are providing valuable information to the interview in relation to the right fit of the candidate to do the job,” she emphasized.

“The conventional question of ‘Tell me a bit about yourself?’ doesn't really provide enough of a parameter to help the candidate know what the interviewer is looking for,” Connie pointed out.

#12

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

hugesteamingpile , Warner Bros. Pictures Report

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C.O. Shea
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

My clarification qurstion...has the person been blind since birth, or later in life so that they may have known colors before?

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#13

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

Tanky50 , DLKR Report

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Victor Botha
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

You cannot drop a round manhole cover through the opening. A square or rectangular one can be dropped through the opening.

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#14

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

Cheese_Pancakes , James Yarema Report

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She added that an unconventional question like "How do you see yourself fitting into the company's long-term goals" is much more valuable. It can show if the candidate has done their research on the company and has thought about their contribution.

Now, speaking about interview questions that are better avoided, she shared that she has never been a fan of generic questions like listing strengths and weaknesses, but there is also not really much of a value in asking questions like "If you could only have dinner with one more person, who would it be?"

#15

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.

nikolacarr Report

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Adrian
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8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Yes, I've had cats and dogs and it helps to understand and work with different personalities...

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#16

"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.

Pumpingions Report

#17

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.

btk12 Report

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Blue Bunny of Happiness
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

So, obviously I had to google it…. The fuzzy covering on a tennis ball is known as the nap. It not only changes the speed of the ball, but also imparts spin to it as the ball travels through the air.

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“There are a number of unusual interview questions that can assess skills,” Connie noted. “But keep in mind that skills don't just mean technical. It also means those soft skills that are important for a team to be effective.”

She added that a good question to assess one of the soft skills would be "What kind of environment do you enjoy working in, and what would you do to contribute to this?"

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"The bottom line, with any interview, the goal is to find out if the candidate is the right fit for the position, and the organization," Connie pointed out.

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

#18

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

praizeDaSun , Sebastian Herrmann Report

#19

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online A friend of mine was asked to solve riddles. He's a programmer.

MistakeMysterious347 , JESHOOTS.COM Report

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Bouche and Audi and Shyla, Oh My!
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Then, in the middle of the game, you run out of riddles. "What has it got in its pocketses, Precious?"

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#20

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online "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.)

blueeyesredlipstick , Sofía Rabassa Report

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Stephanie Goadsby
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Solution to payphone line ups... remove all payphones. Problem solved. 😉

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#21

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

idolovehummus , Bora C Report

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Lotekguy
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

It makes sense for working in a highly stressful environment, but I'd be leery of those who enjoy doing it too much.

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#22

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

festertheinvester , Benjamin Zanatta Report

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#23

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online "What role would you be in a circus?"

Th4t9uy , Becky Phan Report

#24

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

Wind5urfer Report

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Lotekguy
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Tell the interviewer the names of all the pets you've had. No way they knew that before, and easy to do within the time limit.

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#25

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online 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 , Freddy G Report

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Blue Bunny of Happiness
Community Member
8 months ago (edited) DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

Never ask an occupational therapist the sandwich one. Activity analysis is a core skill. Still traumatised by the 3,500 word essay on how you clean your teeth and the 7 page appendix of breaking down all the skills needed eg bilateral integration, form constancy, stereognosis, kinaesthesia etc etc. There’s good reason why we asses people making a cup of tea in hospital.

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#26

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online "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.

Waltgrace83 , Mapbox Report

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#27

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online Would you still interview with us if I was a worm?

owlman17 , Sippakorn Yamkasikorn Report

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Lotekguy
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

"That should be if you WERE a worm, and so far, I'm not impressed with you in your human form." You won't get the job, but you'll have a good story and the joy of not working for that nimrod.

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#28

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

ATXKLIPHURD , Jeremy Report

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Trophy Husband
Community Member
8 months ago DotsCreated by potrace 1.15, written by Peter Selinger 2001-2017

In reality, This depends on the job. But legally you can't take age into account in the US. You can take experience though, so now it's two people the same age and one has experience in this job while the other is an unknown!

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#29

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online Where will you be standing at the office holiday party?

uribelfi , cottonbro studio Report

#30

30 Times Job Candidates Were Taken Off Guard By Interview Questions, As Shared Online My most recent boss threw me the curveball of “what do you think of the word ‘should’”?

Ligmartian , Magnet.me Report

Note: this post originally had 40 images. It’s been shortened to the top 30 images based on user votes.

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