Bosses Share Stories Of The Worst Interviews They've Ever Seen

Bosses Share Stories Of The Worst Interviews They've Ever Seen

There are good interviews, and there are bad interviews. And then there are these interviews. Get ready for some second-hand cringe factor as bosses share stories of the most horrible interviews they've ever conducted. 

Thanks to everyone who contributed! If you'd like to read more stories like this, check out the source link at the end of this article. Comments have been edited for clarity. 

I became the hiring manager for a mom and pop restaurant at 18. I looked really young too, most people put me at about 16 at the time. At any rate, I'd exchanged some emails with a woman wanting to become a server. I was planning on hiring her, as she had lots of experience and seemed really nice. So I scheduled her an in person interview. Keep in mind that I had never actually seen her in person.

So, the day of her interview comes and I just happen to be at the hostess station when she arrives. When I greet her, "Hi, welcome to _____!" She cuts me off with what has become one of my favorite instances of self sabotage I've ever witnessed.

"Alright, listen. I'm about to get hired her as a server. So what that means is that you, as a little hostess, are going to sit me with all the big tables and give me all the good regulars or I won't tip you out at all and I'll make your life living pile of crap. Got it? Good. Now, run along and tell your hiring manager, that I'm here."

I smiled back sweetly and said, "Actually, I'm the hiring manager. I'm sorry to have you come up here for no reason, but I've already filled all of our open serving positions. You have a nice day."

There's no way I'm going to hire someone with that much stupidity AND that poor of an attitude.


I was friends with the hiring supervisor at a job once, who told me this one.

A guy dropped a bag of methamphetamine while taking something else out of his pocket at an interview. He actually could have gotten away with this, as the interviewer is something like 80% blind. However, he said, "Oh, sorry," to which the interviewer replied, "For what?"

His answer? "I dropped my meth."


"You guys would be lucky to have me, Google is trying to recruit me too."

I wished him the best of luck at his job with Google.


A guy once confessed that he was a convicted felon for drug trafficking, and that he actually had no experience in the industry we were in. That guy turned out to be the best employee I've ever had, out of around 200 people I've hired. Unbelievable.


A colleague of mine called this guy in for an interview. He didn't show and about 2 hours after he was due in, he called and said he'd been hit by a car. My colleague decided to give him the benefit of the doubt and they arranged another day. The day arrives and he didn't turn up again. We got a call from him a while later saying he'd broken his tooth on an almond and couldn't come as he'd had to rush to a dentist. My incredibly trusting colleague decided to try one more time another day. The guy turned up drunk.


Me: You mentioned on your application that you are a good leader, could you give me an example of your leadership abilities?

Candidate: "Absolutely! At my last job we hated our Chef and I organized the kitchen staff to walk out during the Friday night rush."


Resume included a startup he founded.

I asked about it: "Tell me about your startup, sorry, what was it called again?"

He forgot.

He forgot the name of the startup he founded a year prior.

It went downhill from there.


I had to interview a guy for some contract labor and when I showed him our work vehicle he shook my hand and said, "I'm sorry but I refuse to drive a chevy" and left. I was speechless... he had been giving me the story of how hard he was having it, so I decided to give him a shot and because we had a Silverado for the work vehicle he turned it down? Man....


Kid was in high school. He put down his friends as references. He had to fill out the application twice because the first time he screwed up.

Me: What made you apply? (I ask this question more to see what type of response that can create on the spot. I like to see if they can formulate a decent response while thinking on their feet)

Kid: Well....umm....all my friends work here so I don't think it would really be like a job to me. More like kickin' it with the homies.

Me: Would your friends being employed here get in the way of you working?

Kid: Maybe. I mean our Auto Class teacher makes all of us split up in class and we can't work together.


I work in software development.

As part of the interview process at my company, our candidates interview over Skype using a code-sharing website for them to complete a small and relatively simple problem to help weed out candidates who are dishonest on their resumes.

In one of my interviews, I started with the usual introduction of myself, my role within the company, so on and so forth. I introduce her to the task and explain that it'll be on a code sharing website and that she'll need to follow the link I will send her to access it. I paste the link into the text window and explain to her how to access it (some people haven't used Skype before and don't know how to access text chat in a video call). She smiles and nods and asks me when I'm done, "will you be writing the link on the whiteboard?"

What whiteboard? I look behind me and remember that yes, there is a small whiteboard behind me, and this woman was expecting me to handwrite the (not so short) link and she would read it off the webcam to type it into her browser. "No," I explain, "I sent you the link within Skype itself. If you'll just click..." I'm forced to trail off as she reaches forward and picks up her webcam (which I'm assuming was mounted to the top of her monitor). I get a nice close-up of her eye as she peers inside the camera, then turns it on its side to observe it some more. I ask her what she's doing. "Trying to find the link," she replies.

Dumbfounded, I once again explain that the link was sent over Skype and wouldn't appear behind me nor on the webcam. She resumes the smile-and-nod routine as I ask her to follow my directions to access the Skype text chat window. I ask her to wave her mouse cursor over my face until she sees some buttons appear. She takes her hand off the mouse, raises it, and waves it over the screen. I explain to her again that she needs to use the mouse and she smiles and nods again.

After about 15 minutes (of a 30 minute interview), she did finally discover the link in the Skype text chat, but she proceeded to type it into her browser by hand.

She did not make it to the next round.


Not the worst, but the weirdest. Guy applied for a warehouse/delivery position. Had emailed back and forth with a few questions before the interview, and it sounded promising. He comes in, sits down and says, "So, what is this position? Delivery? Oh, I can't lift anything. Also, I lost my driver's license a few months ago. I guess we're done here." And then just got up and left. No thank you or goodbye, just got up and left. It was the shortest, most bizarre interview I've ever done.


Back when I was HR Manager for a market research firm, one of the most awkward interviews was with my candidate and his mother.

This 19 year old who apparently had previous work experience in customer service brought his mother into the interview with him. I politely questioned his mother as to the reasoning of her joining in on the interview and I was told, "I'm just making sure this is the right company for him and making sure you're asking fair questions."

I decided to roll with it (why not, this is the most interesting thing I've had all week) so I asked my first question.. she answered for him. I politely explained that the interviews I conduct are with the candidate only unless special accommodations are required. I was told, "I'm not going anywhere."

I thanked them both for coming out and explained that the position requires problem solving and critical thinking on an individual level. Unless I am hiring the both of them under one salary working together as a "full time equivalent", this wouldn't work. I was then told I would be sued and to F myself.


A person who was about 15 years older than I was and clearly didn't understand that I was the one actually interviewing her for the job. This was an engineering position on my team making ~$175K. She was very candid with me regarding her overall personality and actually put her purse on her lap at one point and doing her makeup while we were talking. I guess she thought I was the secretary and she was making small talk before meeting with my boss?


I asked a guy when would he be available to begin work if offered the position... his response was that he would have to put down his dogs in order to begin work as soon as possible but was willing to do that to get the job.

We called him almost immediately after the interview to tell him he wasn't selected and hopefully save his dogs lives.


Interviewing for an international sales rep. in a rural area. Boss' nephew invited himself in and his question was, "what is your blood type?".

I was mortified. Glanced at him then across to the candidate, who had travelled 200klm/120mi for the interview and was better than we'd hoped for.

Annnnnnd you guessed it: best candidate rejected our subsequent offer and boss' nephew said he "wasn't suitable anyway".



Had a girl sit across from me put her elbow on my desk then rested her head flat on her hand so that her head was now sideways. She stayed that way through the entire interview.

Another time I asked a guy if he had any special skills, he replied "Keepin' it real with y'all"


I was once interviewed by a company that wanted an IT god who could do about a dozen jobs solo. We're talking things like security engineer, programmer, database administrator, and more.

Wanted something like 200-300k worth of technician out of one guy. Wanted to pay 12/hr for it.


Guy told us that he applied so long ago he forgot which position it was for. We then proceeded to show him the job description and he said "I don't even know what this piece of equipment is" (it was a maintenance job). He apologized for wasting our time but he got a free bottle of water, so I guess it worked out for him.


When my dad was going through applications, in the "reason for leaving last job" part, a man wrote that he had shot his previous boss in the head. They had told him to be honest.


I've got tons of these. This one is my current favorite.

I had a guy come in for a CDL and site work (truck driving and earthmoving equipment) position. After the initial pleasantries he went on to inform me that he didn't like small talk, his pet peeve is people who socialize too much on the job when there is work to be done, he likes to get right to it and get hammering away on that work he just doesn't understand these people who just talk talk talk instead of getting on with it not like him, he's not interested in chatting no he's got a better work ethic than these darn kids and he's not going to stand around gabbing about nothing when time is wasting etc etc etc.

He went on like that, no exaggeration, for an hour and 20 minutes. A solid hour and a half including the initial question and answer bit at the beginning. I wasn't even mad, I just let him ramble on. At the end of it he asked if he would be starting that day or if I needed to "do some of this paperwork stuff" for him.

He hadn't even filled out his pre-hire information forms.

Absolutely majestic.


A person I know had someone come in for an interview wearing gym shorts and a tank top, fresh from playing tennis in the summer sun.

Another candidate came in with their mother and asked if she could sit in on the interview and help answer questions. The interviewer asked if the mother was the one applying for the position. Without a word, the mother got up and left to sit in the waiting area.


One time an applicant told me that he was temporarily placed in charge of a team, and one of the team members spoke mostly French so he told him to "learn English or get the eff out of here," and then subsequently sent him home when he did not immediately learn English.

The question was "Tell me about a time that you worked well under loose supervision."


I interviewed an Italian girl who couldn't speak English. She had only moved to the country a few weeks prior and I think this was her first interview but it was all so painful. Nearly every question was answered with "si, ...**pause**...yes". Even questions that you shouldn't answer with a yes. I decided to be nice and go through all of my questions but it was ridiculous, like I nearly called an Italian speaker to come and translate for us.

"If you had multiple asks coming from different parts of the business and they were all due today, but you couldn't finish them all in time, how would you try to balance this?"

"si, ...**pause**...yes"

"No, say it's not possible to do them all by today, what would you do?"

"si, ...**pause**...yes"

"So you don't have time to do them all. Would you see if you could re-prioritize any of these, or would you just not do them or something else?"

"si, ...**pause**...yes"

"What I'm normally expecting here is something along the lines of you either asking the someone for more time, or looking for help from a colleague, or even speaking to your manager and asking for a list of priorities from them. Which of these would you be most likely to do?"

"**longer-pause**, si, ...**pause**...yes"

At the end of the interview I was then just asking her general "shoot the breeze questions". She said she was currently learning English. So I asked her where was she learning it, and told me "only for a few weeks". So I said, 'no, the location of the school? Where is it located?' and I get a blank face. I eventually started naming streets, and she goes "ahhh! Dove!" and she tells me the street name.

After the interview I told our recruiter that she can't speak English and we won't be proceeding further. The recruiter told me that she had spent 40 minutes with her on the phone (in English) making sure she understood the role. When I asked her if the applicant said anything more than "si" or "yes", she looked a bit embarrassed.


Just a few weeks ago I interviewed a person for a healthcare position. The question was something like "tell me about a time you were forced into a new situation and how did you deal with it" she proceeds to tell us about the time she was forced to move to an area with "colored people" and how she learned to "deal with them".


We needed an appliance repair guy; they didn't need to have any formal training, but they needed to know what they were doing. The standard test was we tossed 'em in a room with a broken whateverwehadaround and asked them to diagnose it.

One guy completely dismantled it, and couldn't put it back together again. I walked in, and he's got his hat off, he's rubbing his head, muttering to himself surrounded by parts. I asked him to leave.

So the next guy to apply for the job got shown to the same room, and was told 'put this back together'.


I sat in on interviews with a manager at the restaurant I worked at. I remember this application he pulled specifically cause the kid was from the same rough part of town the manager was. The manager comes in on a 5 minute rant on how much he hates scam artists trying to get money off decent people in the streets. Upon hearing this the kid launched into a story about telling people he locked his keys in the car with his wallet and just needed $20 for pop a lock. Explains he could make $300 on a good day. The kicker? He doesn't have a car! He laughs while all of us stare at him dumbfounded. Manager kicked him out he got a job down the street.


I was working as a front end supervisor for a big box retailer going into the holiday season. This was the beginning of November.

I get this girl who came in for an interview and I let her know it was seasonal work, but that we would be keeping some of the seasonal hires after January and inquired as to whether she was looking for seasonal or long-term.

She replied, "Well, I basically got in trouble for bad grades and staying out too late, and my parents are making me pay for my own car insurance this month."

That was it. She just stared at me expecting her to hire her on the spot.

I did not do that. I do still wonder if she ever got a job that helped her pay her car insurance for that month, though.


We had an applicant for a teaching position who stated on his resume that he held a Master of Music degree from Yale.

When interviewing him, I asked what he thought of Woolsey Hall (Yale's primary concert hall) and its renowned pipe organ. By his answer and facial expression, I could tell he'd never been there.

After he left, I called contacts at the university who confirmed that they'd never heard of him and no one by his name had received a degree there.


"I want to begin by stating that the call center I work at is seriously top notch. We pay extremely well, we have extremely flexible hours and we pride ourselves in our local reputation.

Part of this is because of our extremely deliberate hiring process. We get about 100 applicants every week, of whom we will end up hiring 3 to 5.

We really don't hire just anyone, and as a company, we take a great deal of pride in that. So do our clients, all of whom are really high-profile, on a national scale.

So, this morning, my boss, Al, called me into his office and asked me to conduct my very first interview.

Now, I'd very recently accepted a promotion to trainer - so recently, in fact, that I'm not even done with my training - but interviews are the purview of managers and shift supervisors. I mentioned as such, but Al told me that this was a 'special case.'

"We are counting on you," Al said. "With tremendous, tremendous gravity.

"[OurCompany]'s reputation depends on our hires, Derpleberry. I expect a great deal from you.""

With that, he handed me a clipboard with a list of questions and a pen and ushered me into another manager's office to wait for my very first-ever interviewee.

About three minutes later, the kid walked in.

Oh my gosh, did he ever walk in.

I am going to take my time about describing this kid, because I do not want to leave a single thing out.

(And please, keep in mind, like everywhere else, we require business casual and there is no way this kid got this far in the hiring process without being told at least three times.)

He was wearing: * Skinny blue jeans that were so tight I could easily see tendons and bone structure, pulled down around the hips and crotch to avoid mashing his balls into paste. * Beat-up old Converse sneakers covered with what appeared to be homemade Rageface patches. * A red, hooded sweatshirt over a freaking My Little Pony t-shirt. * Black, lensless eyeglass frames and about six facial piercings * A Naturo headband.

A Naruto Headband.

""You're wearing a Naruto headband,"" I said.

Now, to me, my tone said, and quite clearly, 'How the heck did you make it past the first two stages of the vetting process, you ridiculous child?'

He, however, assumed that my tone meant 'Gosh, how completely appropriate!' and said, with an expression of such sheer smuggery I wish I could adequately describe it, "Oh, you recognize my headband. Plus one to you! I was almost worried I'd have to deal with some lame-arse suit!"

And then, he handed me his 'resume'.

I want you to understand how very loose I am being with that word, here, because what he actually handed me was about four pages of prose beginning with the sentence "I was born on [Date], 1988, in the small town of [suburb]."

I stared at this Facebook-profile-styled autobiography in numb shock for about five minutes while he rambled on about 'suits' and how they just don't 'get' anything about anything and I don't even friggin know.

As I flipped through the pages, I noticed two really important things about it:

1) I had initially assumed the kid was about 18, 19 tops, but he was actually twenty-five.

2) There was no work experience in it.

Anywhere at all.

He'd gone to college and that was it, that was his entire resume, everything else was random musings on the books, TV shows and bands he liked and what they'd taught him and how he basically felt that college was completely beneath him. He'd never even held a paper route.

I looked up at this kid and I said, ""Do you think, maybe, you'd like to reschedule this interview for another time?""

"No. Why? Is there a problem?"

"Yes," I said. "Several."

I asked him if he'd received the multiple calls setting up and confirming the interview, all of which had stated, very clearly that we expected him to be dressed 'business casual', and, in fact, had very carefully defined what was meant by 'business casual'.

He said, "Oh, were you serious about that?"

I had no words.

"Well," he continued, in that very same ludicrously smug tone, "I figured, you know, this is me. This is who I am. If you can't 'deal' with that, then maybe I don't even want this job."

"That's extremely convenient," I said. "Because I don't see any reason to continue this interview."

"Well great!" he said with a gigantic smirk. "When do I start?"

What. Holy unbelievable. I am staring at this ridiculous man-child and there is zero irony on his pierced, fake-glasses-wearing face, he is patiently waiting for me to tell him when his first day of work will be and I still cannot stop staring at that effing Naruto headband.

"You don't," I managed to say. "You don't start here. Not today, not tomorrow, not ever. When I said 'this interview is over', I did not mean that in a good way. "

He is still not understanding. "But you didn't even ask me anything," he says. "There wasn't even an interview."

"Yes," I said and explained to him that our request for him to dress like a professional adult was one hundred percent mandatory, and by failing to do so, so very flippantly, had told me everything I needed to know about him.

"You don't know anything about me," this kid says and his face goes beet red. "You don't know me, you don't know anything about me. You need to give me an interview. I know my rights, give me my interview."

For the sake of not causing a physical incident, I did not explain that I knew more than enough about him already to warrant never ever hiring him ever in the world, forever. Instead, I carefully explained that his 'rights' here consisted entirely of leaving the building before I had him removed for trespassing.

And now this kid starts shouting at me, screaming that I am an arsehole, that I don't know about anything, that he's a billion times better than me and when he's a millionaire he'll buy this company just so he can fire me.

When that somehow fails to procure immediate employment, he then, with tears in his eyes, begs me for a job.

His mother, he says, will boot him out onto the street if he doesn't get this job. If I don't give him this job, he will be homeless, he shouts at me, and it will be my fault.

"I'll cope," I tell him as security finally arrives to escort him out.

So there's me, sitting in the empty office, with this kid's ridiculous 'resume' in my lap, chairs all knocked over, staring off into space and wondering what the heck just happened.

And then Al, my boss Al, pokes his head in. His face is stony-serious as he asks me, "What did you think?"

"You know," I said, "I don't think he'll be a good fit."

"Okay," Al says and nods with the kind of gravitas you don't see outside of Shakespeare. "Keep up the good work, Derpleberry."

And he walks away.


Thanks for reading!


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