June 12, 2020 | Maria Cruz

People Share How They Answered A Tough Job Interview Question

Occasionally, job interviews are meant to trip you up. The questions seem unrelated or totally out in left field, leaving you with the pressure of thinking on your feet. These are some of the toughest questions people were asked when applying for a job, and here’s how they handled the situation.

#1 Name That Server

It was a lunch interview and at the end, the manager asked, "Who was our server today?" I didn’t know how to answer, so I just said, “Umm…”  I had zero idea because I was more focused on hearing the specials than her name. It must have made me look like a snob, though, because I didn’t wind up getting the job.


#2 Sniping the Resume

During my interview my boss asked me, “So what made you apply for this position?” All I could respond with was, “I actually have no memory of applying for this job.” Turns out, she actually sniped my resume when I applied for a job debating with insurance companies and decided to see what I’d say in response to her question.


#3 Character Flaws

A friend of mine once got the question, “What is your biggest character flaw that would make us not want to hire you?" After he got out of the interview, he told me he answered with, "I’m so arrogant that I honestly can't think of another flaw that would make you not want to hire me." He didn’t get hired by them.


#4 The Hardest Interview

I interviewed at Cambridge for electrical engineering and it was definitely the hardest interview I've had. I've done multiple rounds of technical interviews with Facebook, Amazon, startups, big consulting firms, etc., but Cambridge was the worst. They gave me progressively harder circuits to solve until I basically choked on a problem that I didn't learn how to solve until my third year of college.


#5 Tough Question

"Would you rather focus on one thing and do it 100% while two other things do poorly or would you rather do three things at 70%?" It was a tough question. I told them off the bat that it was an intriguing question and that honestly, I give 100% in my projects. I added that I hate presenting things that I don't feel are up to my standards.


#6 Questioning Existence

It wasn’t a single question so much as it was their method of deep follow-up questions that eventually got to a point 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, “You’re asking me why I’m alive?” 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 Straight to It

I applied to an administrative job at an elite university on the East Coast and made it to the final round of the interview. It was just me and one other candidate and we both met with one of the vice presidents. The question itself wasn't difficult, but the manner in which it was asked completely threw me off guard.

The VP essentially walked into the room, shook my hand, and before we even sat down, asked me "So, what can you do for me?" I was expecting the first two minutes to be small talk, so I was caught completely off guard by the straightforwardness of the question. I mumbled out an answer, but I knew right away I didn't impress. The interview only lasted another 15 minutes and, needless to say, I didn't get the job.


#8 What is That?

A boss once asked me, "What the heck is gmail.edu?" I answered with, "That's the domain name you get when your garbage 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 mess it up." The good news is that I got the job.


#9 Going Nowhere

I once had a recruiter ask me why I applied for the position during a phone interview. 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 well. We just have your resume.” That interview ended up going nowhere.


#10 Stand By Your Answer

"What is RDP Protocol?" was mine. My reflex kicked in and I said, "My first guess would be someone trying to refer to Remote Desktop Protocol, but tacked on the additional redundant 'Protocol' because they don't know what it means either." I did not get that job, although I stand by my answer, given that the interview was for an IT position.


#11 Event Planning

I got called in for an interview at a business I applied for. They started interviewing me on things 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 that they weren’t asking me questions for the job I applied for. 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. I ended up getting the job in event planning despite having little to no experience in the field.


#12 Hypothetically Speaking

"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 minutes in front of them. It was one of those hypothetical case questions they asked me before I got the job.


#13 Unfair Questions

When interviewing for my current internship, I was asked, "Explain to me why a condo circuit breaker is 208V instead of 240V like a house." For reference, the interview was done on-site walking around. There were a lot of questions like this, and as a third-year biochem engineering student, I didn’t have the answers to a lot of them. But, this was the toughest for me to figure out.

I answered by saying I didn’t know, but then asked him if he could explain it to me. The interview ended up taking two and a half hours instead of one because my now-boss was having fun doing it. He said my honesty and asking got me the job. Apparently, it was something no one should have known because it has to do with how the fans need to operate in the basement.

Some of the people reacted really poorly and got visibly upset that they were being asked "unfair questions.” Other candidates said that they didn't know, but I was the only one who followed up wanting to find out the answer. He told me that he wanted someone who wanted to learn and that was what sold him on me.


#14 Two Days Gone

I applied to one of these annoying start-ups that treat the office like a second living-room and expect employees to act like a close circle of friends. They thought they were really original and fresh. I had an interview over the phone and expected somewhat weird questions. Instead, they made me conduct the interview as if I were the one interviewing them. Honestly, that's a pretty bad idea.

It felt like they wanted to show off how out of the box they are, but they learned hardly anything about their potential employee. It went rather well, nevertheless, since I'm used to interviewing people for my job. In the end, I wasn't offered a position. After having me work on a mock project that took over a day to finish, they told me my work was great but unfortunately, they had already someone in mind for that position,  even before I applied. That's two days of my life I will never get back.


#15 The Good Son

“One day, your parents are going to pass away. After you bury them, you will never talk to them again. They’re gone forever. You will have to look in the mirror and ask yourself ‘Was I a good son to my parents?’ Well, are you a good son?” This was for a post law school and pre-bar exam results interview with a judge. Needless to say, I didn’t take that job.


#16 Engineering Position

I applied for an engineering position which I was very qualified for. I got a phone call from the company asking me to come in for an interview. I sat down and promptly got asked tons of software engineering questions. I'm not a software engineer, but of course, I know some basic programming. So I assumed I would be expected to know some, but that was just in-depth, technical questions about software design. I just completely ruined it and I left bummed.

A couple of days later, I got another call from the company wanting to interview me. This time, set up with a different person. I went back in and got asked a bunch of questions I would expect. Turns out, the software group was looking for more people as well, saw my resume on the systems engineering manager's pile, and decided to interview me. I got the position.


#17 That’s Lazy

Someone I interviewed with asked the typical, “Why should I hire you?” I’ve only ever been asked this once. I told the person interviewing me that it was a lazy question and they brought me in for the interview based on my skills and experience, so that should answer the question. I didn’t get the job and I didn't want it.


#18 Work Or Family?

"If you had an important deadline and your child was also very sick, which would you attend to first? Would you come into work and make the deadline or would you tend to your child?" I almost didn’t take the job once they offered it to me because this question really bothered me. I can’t be the only one either.


#19 Money Hungry

For me, I hate when potential employers ask, “What salary do you want?” I think it’s mostly a trap question to see if you’re greedy or willing to work for peanuts. I always say, “Based on what I’ve learned about this corporation, I’m confident that if you extend me an offer, it will be competitive based on my experience.”


#20 Making Up Stories

I had an interview at Starbucks years ago. They asked me to describe a real event where I fought with a co-worker and the exact steps I took to fix the situation. I'd never been in an applicable situation and told them so. Apparently, it was the wrong answer. It wasn't optional and had to give an in-depth answer. I get that they were probably working off some corporate script, but still not sure what exactly I was supposed to say. Making up stories and making mediocre coffee don't really have much in common.


#21 You Have 30 Seconds

I was interviewing for an analyst position at a bank. During the interview, the guy was friendly and we were talking about all sorts of casual stuff. Then, out of nowhere, his expression became all serious. He asked me, "If an analog clock shows 3:30 right now, what is the angle between the minute hand and the hour hand? You have 30 seconds.” He pulled out a timer that beeps every second as it counted down to zero. It took me about 10 seconds to grasp he wasn't joking, then another 10 seconds to try to collect myself, which left 10 seconds to solve the problem. I failed.

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#22 Turn it Over

I recently had an “email interview” before I had to attend a second in-person interview. No big deal. It was a list of 10 questions. I answered them. Double checked my work. Submitted. When I got to the in-person interview, the dude laughed at me and asked how I had such “attention to detail” when I’d only answered half of the questions. I just sat there stupefied until I asked him if the rest of my email was on the back of his paper. It was. He had printed double-sided and not even checked. But the hardest part of answering was my own stammering and trying not to call him out for his own mistake.


#23 All That Work

About seven years ago, I interviewed for a job with EMC (think big data storage company). I went through about eight interviews, including a panel and questions. All seemed to go well, but the big guy wanted a one-on-one since he couldn't make the panel. He then began spitting off over the top questions to me, just to get me to say, “I don't know.” It was very difficult as I was presenting on a whiteboard my own storage array topology. Obviously, I didn't get the job.


#24 Harshest Critic

I was asked if I'd rather do my own annual "self-evaluation" — including a list of goals and objectives for the forthcoming year. Either that or have a department head fulfill this role. I opted for self-evaluation, stating that I'm my own sharpest critic and always striving for improvement. That worked well for the interviewer as it displayed determination coupled to the ability to work independently.


#25 The Top Answer

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 three months later. They asked me, “So you applied three months ago and were turned down. Why do you think you’ll get it this time?”

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, I 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.”

I added, “I've 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 help or advice. I’m doing small parts of the manager's role every day.” I got the job, and in my feedback, they said it was between me and someone else. It was incredibly close, but I got the job based on that answer. So, I’m pretty proud of myself.


#26 Motor Mouth

"What do you feel are your biggest weaknesses?"Jesus, I just could not stop talking. I honestly just kept digging myself deeper and deeper into a hole. I guess I thought they'd appreciate my honesty. Eventually, when I'd run out of actual weaknesses, I started inventing some more examples. I did not get the job.


#27 Is This a Joke?

"If I asked your friends to describe you, what would they say?" I think I played it more as a joke and said they've been my best friends for years including college, so they'd say whatever they could to get me a job. I don't think that was the best answer, but I ended up with the job and told the recruiter afterward that it was an uncomfortable question.

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#28 Tell Me a Story

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.


#29 Conflict Resolution

I had an interview for a project engineer position. The interview question was, “What would you do if you purchased and installed a new piece of equipment and then have the line supervisor tell you that they gave you the wrong specs?” I think it’s an excellent question that caught me a bit off guard because it demonstrates your conflict resolution and problem-solving skills.


#30 Turning Us Down

A question that sort of took me by surprise at the end of the interview was something among the lines of, "What reasons would make you refuse the position if you got the job?" I was flustered and hesitated many times. I ended up saying something cringey like, "I tend to give new opportunities one chance, either way, it will be a learning experience.” I got the job and have been working there for nine months.


#31 Favorite Superhero

I interviewed with Marvel. The interview went incredibly well and the last question they asked was, "Who is your favorite hero?" To this day I regret not saying Agent Phil Coulson and just going with Spiderman because there was a giant Spiderman mural on the wall next to us. I don't work there full-time, but they do hire me out as a freelancer from time to time, which is really cool.


#32 All Possibilities

Recently I was asked, "If you can have dinner with any deceased person, who would it be?" I was unprepared and blurted "Nikoli Tesla" and then went on a three-minute tangent about how Edison betrayed him. No, the job had nothing to do with physics, it was marketing. I also got asked to write down how many things you can do with a newspaper and was given 10 minutes to write as many as possible. One of my answers was, "Cover a car as a prank.” I'm working at that job now.


#33 Under Pressure

For a pharmaceutical sales job interview, we were going through the standard questions when all of a sudden, I was asked, "If a case of 12 bottles costs $36, how much per bottle?" Then, rapid-fire, the interviewer changed the case price so that the calculations became more and more complicated. It's not about math. It's all about how you handle pressure. Do you guess? Do you lie? Do you sweat, panic, or get upset? They want to see that you keep your cool, yet continue to pursue the answer or promise to get that information for the “client.”

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#34 Lone Wolf

I had an employer once ask me something like, “What is your worst quality?” I told them that I wasn't a good team player and greatly preferred to work alone. I also said I knew it wasn't a good quality to have in that environment, but it was something I was actively working on fixing. I wound up getting the job.


#35 Wait and See

I had progressed to the final round of interviewing and it was the boss's task to interview the final candidates. First question asked was how many drinks I could handle. It was an interview for an office job and the question had zero relevance to neither position nor industry. I really wanted the job, but it was clear that the guy had zero interest in the whole interview process. I just replied that he'd have to wait until the office Christmas party to find out. I got the job.


#36 Can You Be More Specific?

None I could say were the hardest, but a few questions I always find it difficult to answer are super non-specific, open-ended questions. It just seems lazy on the behalf of the interviewer. I think the one I struggled with the most was for admin for an office supply company. It was a two-hour slog in a stuffy, dark office. Everyone there seemed super depressed. Interviewer then hit me with, "Why should we hire you over other candidates?" at which point I just said, "You need admin experience and I have it.” I didn't appreciate a 1.5 hour written personality test followed by half an hour of excruciatingly inane questions for $14,000 a year.


#37 Sell Me This Pen

In an interview for a sales job, I was handed an ink pen and asked to sell the pen to the interviewer. I laughed a little bit, then looked at the pen for a second. I described its amazing features one by one and was over-the-top cheesy about why this pen was the best pen. I got the job, but I think only in spite of that answer.


#38 Three Jobs

"You're working three jobs right now?" That was asked by a panel of management as I interviewed for a job that paid $35K. They were skeptical, until three of them simultaneously got their phones out, dialed the number to each on my resume and asked to confirm if I was going to be in on whatever day. I just sat there looking each of them in the eye until they hung up and they admitted they were impressed. I  breezed through the rest of it and was offered that day.


#39 Describe This Color

"Let's say you are talking to someone who has been blind since birth, how do you describe the color yellow to them?” This was in an interview for an IT helpdesk position. I just looked at the guy for a second like, “Are you serious right now?" I stumbled through it, mentioned warmth like the sun and just stammered. He acted like it was a perfectly normal thing to ask and said it was a way to gauge my ability to get technical information to someone who wasn't geeky.


#40 On the Radio

A few years ago, I applied for the position of a radio DJ. One of the questions was to pick which new releases would fade fast or stay around a long time. I picked Hozier and his song “Take Me to Church” as one that would probably fade away quickly. I didn’t get the job and I can still hear Hozier on the radio.


#41 Here Lies a Good Person

I had a guy ask me what I wanted it to say on the epitaph of my gravestone when I pass away. This was for an internship when I was about 20. First, I had to ask what an epitaph was. It threw me off guard and I just sort of stammered and said, 'Uh, that I was a good person." The interviewer then asked, “So you want it to say, 'Here lies a good person?’”


#42 Group Interviews

I tried to get a job as a teller at Wells Fargo once. In a group interview, they asked, "If you could be a fruit what would you be and why?" I'll be honest, I don't even remember my answer but it was probably something stupid like the question. I cringe thinking about that whole interview. I get nervous in normal ones, so a group one was a nightmare.


#43 Salary Expectations

In a first-round telephone interview for my first job out of university, I was asked, “What salary would you expect?” It totally threw me. There had been no salary on the advert, and at that point, I wasn't even sure if it was a permanent position or something more like a glorified internship. Plus, it was a startup, so I had no idea what their funding position was. I took a punt with a pretty modest answer and ended up getting 50% more than I'd asked for!


#44 Still Don’t Know

I was asked this for a technician job. “You’re having problems figuring out what’s wrong with this machine, the internet is down, no one is around to ask for help, there is no technical manual, and your multimeter, oscilloscope and other tools don’t work. How do you fix the problem?” I replied, “I don’t know.” I still don’t know months later.


#45 Show Your Pants

I just had a video interview the other day and they asked, “Sir, can you please stand up so that we can make sure you’re wearing pants?” I couldn’t tell if they were joking or not, so I proudly stood up to show them. Luckily, I dressed as if it was an in-person interview. Still a weird question to ask someone, though.


#46 Wrong Answer

A friend was in an interview where they asked if he had any prior experience in the specific environment. He replied to the female interviewer with, "No, but experience doesn't matter much. If it did, more guys would marry ladies of the evening." I’m sure you already guessed it, but my friend didn't get the job.


#47 That’s Interesting

“What's one thing you could do without in your previous positions?” It was an interesting question and I struggled a bit, but finally answered that I loathe to speak to pushy salespeople over the phone when I already turned them down or sales reps in general. I work as Sys Admin and was also responsible for buying IT Equipment. I don't know if it was Important, but I got the job.


#48 How Do You Feel?

"How do you feel about women and minorities in the workplace?" I was really asked this during an interview for an engineering technician trainee position with the local department of highways office. I didn't even know how to answer it. I said, "I'm fine with it?" I blew that interview big-time anyway, so it didn't really matter.


#49 Presentation Skills

I had an engineer job interview where they asked me to prepare a 45-minute presentation on myself with an additional 15 minutes allocated for questions and answers. I prepped well for the presentation and thought I did a good job on it, but I didn't get the job. The rest of the day was filled with interviews too.


#50 Proving a Point

I remember one time I was interviewing at a Wendy's and the guy interviewing me thought I got fired from my last job. So the whole interview, he just kept fishing for that answer and no matter what I said, the dude wasn't convinced. I didn't handle it well. I was 17 and was kind of getting ticked off at that point. I just pulled out my phone at the end and called my old manager to prove it to the guy. I didn't get the job.




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