The Most Shocking and Uncomfortable Job Interview Questions (and the Companies That Ask Them)

Seinfeld's George Costanza (Jason Alexander)
Seinfeld’s George Costanza (Jason Alexander) answers tricky questions during a job interview | NBC

Life throws us curveballs. And so do hiring managers during job interviews. Specifically, those curveballs come in the form of strange, and sometimes downright insane, interview questions. We all expect some standard questions, like what our strengths or weaknesses are, or why they should hire you. But you may get a wildcard question asking you to figure out the square root of an obscure number. Off the top of your head.
Can you handle that? And what do you do when you have no clue what the answer is? Sometimes you don’t need the right answer. You just need any answer — any answer you can justify. But some employers like to take things to the extreme. A new report from Glassdoor has outlined 27 of the toughest job interview questions out there, and which companies like to ask them.
“Even with all this research ahead of the big interview, there are some interview questions that could catch you by surprise. During today’s tough interview process, almost any can be thrown your way, so you need to be prepared for anything,” the Glassdoor team said.
“To help, we’ve identified 27 Jobs With Tough Interview Questions to give you a better sense of the tough, strange, and unexpected questions that can be asked in any job interview in any industry.”
Here are the 27 questions and the employers that like to ask them. Have you ever been asked any of these crazy job interview questions?

1. ‘How do you explain a vending machine to someone who hasn’t seen or used one before?’

Bottles of Coca-Cola sit in a cooler
Bottles of Coca-Cola sit in a cooler | Justin Sullivan/Getty Images

This question is levied at candidates for the position of global data analyst at Bloomberg. It’s a bit of a mind-bender, too — which is the point, of course. It’s meant to test you in a couple of ways, including your ability to think on your feet. But it’s also trying to see how you think through problems, and how mechanical your mind is. If you can describe a machine and how it works, it’s a good sign.

2. ‘How many fire hydrants are there in Los Angeles County?’

Firefighter running along the road in all of his gear
Firefighter running in full gear |

You’ll come across this question if you’re applying for the position of software engineer at Disney Interactive Studios. It’s a bit mathematical, and also a bit logical. And again, it’s meant to see how your mind works, and how quickly you can reach a conclusion. You could probably try to figure out the overall population of the county and divide by the hydrant needs of that population. But who knows?

3. ‘If your current employer had an anniversary party for you, what five words would be written on the cake to describe you?’

Slice of coconut cake with fork in a plate -- and the subject of a job interview question
Slice of coconut cake with fork in a plate — and the subject of a job interview question |

If you want to become a district manager at Express — a popular clothing shop for both men and women — you might get hit with this question during the job interview. It’s not nearly as crazy as some of the others on this list, but could possibly throw you for a loop. The best way to handle a question like this? Have a sense of humor, and come up with something memorable.

4. ‘Who in history would you want to go to dinner with and why?’

Men drinking coffee in a restaurant
A group of men drinking coffee in a restaurant | General Photographic Agency/Getty Images

If you’re hoping to become a flight attendant for PSA Airlines, be prepared to answer this question. It’s a question you’re more likely to run into at a dinner party or with buddies at happy hour, but it can also provoke some interesting reactions and answers from job candidates. Give it some thought, and don’t just go for the default answers, like Jesus, Donald Trump, or Abraham Lincoln.

5. ‘Prove that hoop stress is twice the longitudinal stress in a cylindrical pressure vessel.’

Actor Nick Tate in Space: 1999
Actor Nick Tate in Space: 1999 | ITV

If you can even decipher what in the hell the folks at SpaceX are talking about when they ask you this, you’re probably going to be OK. This is a question asked of candidates for the position of test operations engineer, and, obviously, it goes way over the head of the layman. This position requires a lot of specialized knowledge and skill, and if you’ve made it to the interview process, you’ll probably be OK.

6. ‘What’s the capital of Canada?’

Canadian fans celebrate their team's victory
Canadian fans celebrate their sport team’s victory | Alexander Nemenov/AFP/Getty Images

Want to be a team leader at OpticsPlanet? You’ll need to know your capitals. Foreign capitals. Like the one closest to us — in Canada. For those of you who don’t know, the capital of Canada is Ottawa — not Toronto or Montreal. This may seem like a stupid question, but you’d be surprised to learn that many Americans can’t even name the capital of the United States.

7. ‘Name a brand that represents you as a person.’

An Under Armour Spiderman shirt -- perfect for a job interview
An Under Armour Spiderman shirt — perfect for a job interview | Amazon

This question is levied toward candidates for brand strategist positions at Twitter. And when you think about it, it’s a pretty good, pointed question for someone who wants to work in that realm. It also digs into your psyche a bit and gets a feel for how quickly you can come up with a coherent answer. Of course, you wouldn’t want to say “Haliburton” or anything like that. Maybe Nike? Because when it comes to work, you “just do it”?

8. ‘Estimate how many employees are in the next building.’

Manhattan skyline
The Manhattan skyline is viewed from Brooklyn in New York, New York | Spencer Platt/Getty Images

If you want to be a data scientist at the firm Risk Management Solutions, they’ll want to make sure you can think logically and mathematically. That’s where this question comes into the mix. You can probably manage to come up with a logical answer by looking at the number of floors, and by estimating how many people work on each floor. You’re not going to nail it, of course, but it’s a simple and effective test.

9. ‘How many happy birthday posts do you think Facebook gets in one day?’

People are seen in front of an light installation during a press preview of the Facebook Innovation Hub
People are seen in front of a light installation during a press preview of the Facebook Innovation Hub | Tobias Schwarz/Getty Images

Yes, this is a question asked by Facebook’s hiring team. Specifically, candidates for positions in sales operations at Facebook end up trying to answer this one. And again, it’s a question that’s looking at your math and logic skills. If you know how many people use Facebook, you can probably devise an estimate of how many people have a birthday on any given day, and go from there.

10. ‘If you could take anyone on a road trip with you, who would you take and why?’

'Road Trip' | Montecito Picture Company
Road Trip | Montecito Picture Company

Again, don’t just say Jesus. That’s a cop out answer, and an interviewer knows it. And if you want to be an educator at lululemon, they’ll want to hear some creativity and honesty come out of you. You can name a family member and hit them with a sob story, or you can get really creative and name an ancient philosopher or obscure celebrity. Perhaps actor Shia Labeouf would be fun on a road trip?

11. ‘What is the first thing you’d print with a 3-D printer if you had one?’

Experiencing issues with a printer in Office Space
An office worker experiences issues with a printer in the film Office Space | 20th Century Fox

Now, this is a fun question. Well, maybe, if you’re creative. If you want to be the next Linux systems administrator at Rackspace, you’ll need to give them a good answer, too. This is an opportunity to be creative. It may seem like a crazy, intimidating question, but think of it as a chance to be funny or lighthearted. Maybe you need a Bible, so you can pray the interview gets easier?

12. ‘If you had to take only one item to a deserted island, what would that be?’

Tom Hanks in Cast Away
Tom Hanks in Cast Away | Twentieth Century Fox Film Corporation

Again, don’t opt for the easy default answer, like “a life raft.” Or “a satellite phone.” The people interviewing you for a customer service specialist position at Squarespace want you to try a little harder than that. You can go for the Dwight Schrute answer, which is “Physicians’s Desk Reference — hollowed out. Inside, waterproof matches, iodine tablets, beet seeds, protein bars, NASA blanket, and, in case I get bored, Harry Potter and the Sorcerer’s Stone.”

13. ‘Please describe an instance where you had to make a decision without all of the necessary information.’

Investment chart and dice
Taking a risk |

A super meta answer to this question would be to reference the question itself in your answer. Because you’re trying to decide how to answer it without knowing what they want — crazy, right? If you’re trying to get a position on the analytics team at athenahealth, this question may come up. Of course, you don’t want to be a smartass, so try coming up with a real answer.

14. ‘How do you reverse a text string on the Unix command line?’

computer programmer writing code on a computer
Computer programmer writing code on a computer |

This one is asked of candidates for the position of developer at Capital One. And like people interviewing at SpaceX, it requires some specialized knowledge and skill to answer it. It’s a fair question, and if you really feel you deserve to be a developer at Capital One,  you should be able to answer it. If you can’t? Time to do some more homework until you have an answer for the next interview.

15. ‘If you are in a boat with a boulder and you drop that boulder into the lake, how does the water level before and after you drop the boulder in the lake compare?’

Willow Lake, headed toward Kit Carson
Willow Lake, Colorado |

Apple’s hiring team asks this of candidates for the position of mechanical design engineer. It’s a fair question for mechanical design engineers, as it’s actually probing your knowledge of math, physics, and other things. It’s basically a question about displacement — and if you’ve studied mechanical engineering and/or design, you should be able to answer it competently.

16. ‘You have been asked to lead a multi-million dollar, multi-year grant that will be supported across several companies and universities. How do you start?’

Melissa McCarthy in The Boss
Melissa McCarthy in The Boss | Universal

If you want to be Mr. or Ms. future research scientist at the Ford Motor Company, you’ll need to be able to get past this doozy question during the interview process. This question is entirely open-ended. You can answer however you want, in any number of ways. But if you don’t know anything about what the question is addressing, it’ll be hard to BS your way through it.

17. ‘Sell me on one idea, and then sell me on the opposite of that idea.’

David O. Russell
American film director, screenwriter, and producer, David O. Russell | BAFTA.iorg

Here’s another interesting, open-ended question. This one is asked of candidates for the position of Solarwinds administrator at Blizzard Entertainment. This one will also test your ability to be creative, and also to construct and deconstruct an argument. Pick anything you’re familiar with and take it apart. Then put it back together again. It could be something like universal basic income, or the idea that you deserve the job.

18. ‘How would you go about to find the top five Java developers in a certain area?’

Worcester, Massachusetts on a map -- perhaps where all those recruiters are hiding?
Worcester, Massachusetts on a map — perhaps where all those recruiters are hiding? |

If you want to become a technical recruiter for Google, they’ll want to know you can track down people with the skills they need. If you’re unfamiliar with recruiting, you’ll probably have no idea. If you do have experience, you likely have a few tricks up your sleeve for finding people with particular skills.

19. ‘What is the probability of an integer from 1 to 60,000 not having the digit 6?’

A young woman perplexed by a math question
A young woman perplexed by a math question |

If you want to be a quantitative developer at Akuna Capital, you’d best be able to work numbers in your head. This is one of those questions that leave most of us slack-jawed and wide-eyed. If this is out of your element, you might as well throw out a guess. But if you’ve been trained to think in this manner, do the math. Give them an answer, and see what happens.

20. ‘If you were a Muppet, which character would you be?’

Fozzie, Miss Piggy and Kermit in The Muppets
The Muppets | ABC

Finally, a fun question. Unless you’re unfamiliar with The Muppets — which may be the case, depending on your age. Most of us do have at least an idea of what or who the Muppets are, but outside of Kermit or Ms. Piggy, it might be tough to come up with an answer. When in doubt, just say “Animal.” That’ll go over well, and get you a job as a donor family advocate at LifeNet Health.

21. ‘Give me 48 cents using six coins. Tell me the quantity and value of the six coins.’

A man counting out coins
A man counting out coins |

This question is asked by hiring managers at Wintec for the position of human resource manager. It’s not actually that complicated of a question if you can streamline your thinking, work out some algebra in your head, and explain your answer. Here’s a hint: You know right off the bat that three of them are going to be pennies, and one is going to be a nickel.

22. ‘Write an equation to optimize the marketing spend between Facebook and Twitter campaigns.’

Matt Damon in Good Will Hunting
Matt Damon in Good Will Hunting | Miramax Films

It’s not all food deliveries and rides. If you plan on becoming an analyst (data science) at Uber, you’ll need to face questions like this one in the interview. This isn’t an unreasonable question, but it can be incredibly tough. For Uber, it’s a way to thin out the herd of applicants. If you can put pen to whiteboard and knock it out of the park, you’re likely way ahead of the curve.

23. ‘What is the angle at 3:15?’

Sleeping man with a clock
Sleeping man |

You may think that the only real response to this question is “what’s your angle with this question?” In fact, there’s a pretty good chance, you won’t have any idea what they’re talking about. A good guess, though, would be to look at the hands on a clock at the time 3:15 — at which they’ll both be over the “3.” Meaning that the angle is zero … Unless it’s a trick question. To become an implementation consultant at Fast Enterprises, you’ll need an answer to this one.

24. ‘What part of the newspaper do you read first? What does this say about you?’

Two men dig into today's headlines
Two men dig into today’s headlines | George Marks/Retrofile/Getty Images

Want to work in the audit department at BDO USA? You’ll need to talk about newspapers. If you haven’t touched a newspaper in years, then think about what news websites you visit, and what stories or sections you gravitate toward. Then, of course, you’ll need to justify your answer. Again, be creative, and have a sense of humor. It’s a chance to have fun, so jump on it.

25. ‘If a co-worker had an annoying habit, and it hindered your quality of work, how would you resolve it?’

Coworkers deal with each other's quirks
Co-workers deal with each other’s quirks |

This is less of an “if” question and more of a “tell us about a time” question. It’s asked to candidates for the position of production technician at Procter & Gamble, and it’s another opportunity to be creative and to bring some non-fiction history into the mix. They just want to see if you can deal with people, and if you have social skills. Nobody wants a weirdo in their ranks, and this question is designed to weed them out.

26. ‘Throw your resume aside and tell me what makes you you.’

Actors David Spade and Chris Farley in Tommy Boy
Actors David Spade and Chris Farley in Tommy Boy | Paramount Pictures

This one is for sales executive candidates at Zillow. And it really doesn’t get much more open-ended than this. This might be the easiest or hardest question to answer. Most of us have a hard time talking about ourselves and use a resume as a bit of a cheat sheet. So, when answering, take it any way you want. It doesn’t all have to revolve around your career, either.

27. ‘How would you find the square root of 1.2?’

Charlie (Charlie Day) from FX's It's Always Sunny in Philadelphia during a job interview
Charlie (Charlie Day) from FX’s It’s Always Sunny in Philadelphia during a job interview | FX

For hardware engineer candidates at Jump Trading, this question might pop up. The answer? Well, you would divide 1.2 by itself (wrong, don’t say that!) — which most of us can’t do in our heads. But engineers need to know this stuff, and if you can’t answer this question, you may be in over your head.