'Why did you choose to wear those shoes today?': 10+ Workers share the hardest interview questions they've ever had to answer

Author image for Brad Dickson
Brad Dickson • Managing Editor
Feb 26, 2024 10:00 AM EST

Interviews are never easy, the pressure of bidding for your own dreams and livelihood can cause you to slip up and miss the chance at your dream job—failing a pivotal moment of your career. They can even cause you to become so nervous that you miss a shot at a job that you're well and truly qualified—or even overqualified—for.

Of course, this is the case even when interviews follow a predictable course, asking all the common questions that test for aptitude, probe for personality flaws, and seek to trip candidates up and expose their red flags. Some interviewers follow a more unorthodox approach, using their own methods (or one they derived from a self-help book about management 20 years ago) in order to sniff out candidates they think that they want to work with.

These workers shared the most challenging interview questions they were ever asked, some aced their tests with flying colors while others fell flat on their faces.

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  • 01
    What is the hardest job interview question you've had to answer and how did you handle it?
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  • 02
    BEST KEPT AS ELSE'S
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    laterdude It was a lunch interview and at the end, the manager asked: "Who was our server today?" "Uhmmm... I had zero 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. ✩ 18.4k ↓ Share [deleted] Hit them back and ask if they remember the Hostesses name. Establish dominance. 8.3k ↓ Share ●●●
    via u/EveningGiraffee
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    Isolatedwoods19 My boss: "So what made you apply for this position" Me: "I actually have no memory of applying for this job." Turns out she sniped my resume when I applied for a job debating with insurance companies and decided to see what i'd say. 16.3k Share ●●● [deleted] i had a recruiter ask me the same thing during a phone interview and when i told them "i don't know, i've been applying for a lot of jobs lately" their response was "honestly, we don't know what position you've applied for as
    via u/EveningGiraffee
  • 05
    [deleted] Friend of mine got the question: "what is your biggest character flaw that would make us not want to hire you?" He told me he answered: "Im so arroganti honestly cant think of another flaw that would make you not wanna hire me." EDIT: wow highest comment ever for me and its about a friend acting like a .... I might even tell him about this 13.4k ↓ Share
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    spectre73 "You're in Boston but not in the USA. How can this be?" I said "There's a Boston in England." Correct answer was it's before the American Revolution. I got the job. 12.0k ↓ Share rampant_cellotaping What could they possibly hope to investigate with that question? Your ability to obtain the one ring to rule them all? 5.0k ↓ Share
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    136win136 I applied for a management role in 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 3 months later. They asked me "so you applied 3 months ago, and were turned down, why do you think you'll get it this time?"
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  • 08
    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. So volunteered to coach the group of new starters we had. I took customer escalations where they've asked to speak to a manager myself and resolved them. Ive made myself a presence in the office so that if there is an issue and there isn't a manager around, staff come to me for
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  • 09
    I got the job, and in my feedback they said it was between me and someone else, and was incredibly close, but I got the job based on that answer, so I'm pretty proud of myself. Share 11.4k ●●●
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    kiosdaemon197 For the Cambridge interview the questions asked are usually to gauge how you think, so you are encouraged to voice out any and all thought processes For my question I had to calculate the amount of blood in a body, which turned out to be less than that of a normal adult human being. The professor asked, "why do you think that is so?" "maybe the human is smaller in size" "and we call those...?" "pre adolescent beings" ↑ 9.3k ↓ Share
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    Sheepishly_Ragtag "Would you rather focus on one thing and do it 100% well while two other things do poorly or would you rather do three things at 70%?" It was a tough question. Edit: Sorry I didn't fully answer. I told them off the bat that it was a intriguing question and that honestly I give 100% in my projects and I hate presenting things that I don't feel are up to my standards. ✩ 9.0k ↓ Share
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    sixdollargrapes "So tell me, why did you choose to wear those shoes today?" "Umm...what?" 7.8k ↓ Share FlappyBoobs "I Like to keep a layer of material between my socks and the ground" 9.1kShare
    via u/EveningGiraffee
  • 13
    MintberryCruuuunch What do you like about yourself? Uh. Didnt get the job 7.7k ↓ Share LaTroyHawkins "My self loathing makes me a very introspective and reflective person, so I am better than the average person at finding my faults, and developing ways to improve them" ↑ 5.5k ↓ Share
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  • 14
    LFreeze It wasn't a single question so much as it was their method of deep follow-up questions that eventually got to a point to where they basically asked me why I'm alive. Not as a "What's your motivation in life" sort of way, but in a "Why do you exist, human?” way. I repeated to them "You're asking me why I'm alive?" And 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 before. ↑ 7.0k ↓ Share
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    fmoss is gmail.edu" your "That's the domain name you get when college deletes your email address and you have to change your resume over from your school email address to your personal email address and you up." Got the job. "What the 6.5k Share
    via u/EveningGiraffee
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    RepsForHarambe92 I got asked to sell them a pen the interviewer pulled out of her jacket. I had watched "the wolf of Wall Street" three times already and after what they explained to me previously I wasn't interested in the job any more so pretty much re-enacted the scene. Still got the job. ↑ 6.3k ↓ Share ●●●
    via u/EveningGiraffee
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    WeirdWolfGuy "In the event of a fire in the building is your first priority to pull the alarm, or call 911" Caught me off guard, and said 'pull the alarm'. correct answer was 'both'... 6.1k Share EveningGiraffee OP Surely they both can't be first priority, I think you were right as pulling the alarm usually signals to the emergency services anyway! ↑ 5.5k ↓ Share
    via u/EveningGiraffee
  • 18
    Economy Cactus About a year ago, I got called in for an interview at a business I applied for. They started interviewing me on questions that seemed kind of strange. Questions like "Can you tell us more about your event planning experience." I was thrown off, and it became clear when the interview was about 3/4 of the way through that they were not asking me questions for the Job I applied for.
    via u/EveningGiraffee
  • 19
    They were interviewing me for an event planning position and I applied for a job in tourism and marketing. I finished the interview, shook hands and went on my way. Ended up getting the job in event planning despite having little to no experience in the field. 5.5k ↓ Share
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  • 20
    AT1787 "The company is rolling out a new customer rewards cards across the country but they're not sure if it 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 mins in front of them. It was one of those hypothetical case questions they asked me before I got the job. ↑ 4.6k ↓ Share ●●●
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    smokemonster815 "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?" -sing in a really high opera voice and shatter the blender's glass, of course! 4.2k Share
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    hankpym35 Dude sat back and said "impress me". So I jokingly asked if he wanted me to do a magic trick. The interview did not go well lol 420 Share ●●●
    via u/OctavioMasomenos

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