Crazy Interview Questions and How to Prepare for Them

crazy interview questions

“Have you ever stolen a pen from work?” “Why are manhole covers round?” These are actual interview questions that companies—in fact, even very big companies—have been known to use. Chances are you may face some crazy interview questions during your own interviews. When you do, it’s important to know what interviewers are actually looking for (hint: it’s not the “right” answer).

Preparing for Crazy Interview Questions

Nathaniel Chapman is head of life sciences recruitment at Proco Associates. “As a candidate, you must believe in the process, there is a reason why companies ask these type of questions,” says Chapman. “You should remain calm, take your time to collect your thoughts and understand the question. These are questions that you cannot really prepare for, at least not in the traditional way.”

Companies today, says Chapman, not only want to know that candidates can technically perform the role and that they have the right qualifications, but that they also can think independently. “Interviewers today are not necessarily looking for the right answers to different, or ‘crazy’ interviews questions, but they want to evaluate how you think on your feet, face adversity and want to put you outside of your comfort zone,” he says. His advice: “Think outside the box, and answer honestly. It might not be comfortable, but try and have fun with it and let your personality shine through!”

So what are some of the crazy types of questions that recruiters and interviewers are known to ask? Here’s a roundup from a number of recruiters.

Also read: People Who Always Get Job Offers Have These 5 Things in Common

Types of Crazy Interview Questions to Prepare For

Chris Chancey is founder of Amplio Recruiting, a multi-city staffing agency that connects companies with the dependable refugee workforce. Chancey says, “I have asked questions that candidates may have considered strange, but the answers to which were extremely helpful in making hiring decisions.” Among them:

  • How would you give directions to City Hall to someone who doesn’t speak English, and you don’t speak their language?
  • If you had only five minutes to leave your home before it and everything in it vanished into thin air, what would you take with you and why?
  • If you had to leave the U.S. and move to a different country, where would you go and why?

Like Chapman, Chancey stresses that there are really no “right” answers. “After hearing a year’s worth of answers, however, I can honestly say that there are many good ways to answer them. The trick is simply for job seekers to keep in mind the skills, personality traits and personal beliefs that are well-suited to the work in question.”

As a professional recruiter for 20 years, Matt Dodgson, director with Market Recruitment, says he’s been evolving his line of questioning over the years to find the best candidates for his clients. “I’ve found that asking non-traditional questions like ‘Why are manhole covers round?’ gives me a better sense of the candidate than his resume and boilerplate responses to questions like ‘What is your greatest weakness?’.’ These types of questions, he says, “allow us interviewers to better evaluate your emotional intelligence, potential to fit in with company culture and ability to think critically and creatively.” He offers some examples of creative questions he’s used and the type of responses he’s looking for:

  • Pretend I’m your previous boss and we’re doing a 360 evaluation. What rating would you give me and what advice would you give me? Here, says Dodgson, “I’m not trying to get actual constructive feedback but, rather, I want to get a sense of how you evaluate your own strengths and weaknesses and how you operate under supervision. The best way to prepare is to think of how you have learned from your former boss. Is there a certain soft or technical skill that you aced under her management? What are some weaknesses that you are working on but wish she could have helped you better with?”
  • What would you do if you won the lotto? “I find that this question is a better way to ask about people’s passions outside of work,” says Dodgson. He advises job seekers to prepare by thinking about their ideal work/life balance. “If you were to become a millionaire, you might not have to work, but the fact that you want to shows your dedication,” he says. As a side note, he offers: “Don’t be afraid to ask a follow-up question such as ‘How much would I win?’ It shows that you like seeking clarity and don’t make assumptions.”
  • What will you do if you do not get this job? Be careful here, Dodgson cautions. “The worst possible responsible response to this question is to be cocky and say, ‘Why wouldn’t I get it?’ I ask this question to get a sense of how resourceful candidates can be and how determined they are to get a job in their chosen line of work. I also want to try to gauge if they are interviewing at different companies.” The best way to prepare for this type of question, says Dodgson, is to have a good job search strategy. “Show that you are resourceful by coming up with ways you can remain connected with the company to learn of future opportunities,” he suggests.

Also read: How to Prepare for and Ace a Second-Round Job Interview

A Strategy for Responding to Crazy Interview Questions

Finally, Lynn Whitbeck, online career mentor at, offers an approach to responding to any types of crazy questions that might come your way based on the acronym PICKLE:

  • Pause and gather yourself before responding.
  • It does not matter why they asked this oddball question.
  • Control your emotions, no eye rolls or frustrated sighs.
  • Keep in mind this is an interview.
  • Let go of any attitude or annoyance, and respond in a professional, courteous, and friendly manner.
  • Express your answer with honesty and civility, no matter how silly the question.

Crazy interview questions represent an opportunity to convey your personality and ability to think on your feet. When crazy questions come your way—and they will—following the advice offered by these recruiters can help you put your best foot forward.

Looking for More Support with Interviewing?
Check out our Collection of Interviewing-focused Articles 

About the Author

Lin Grensing-Pophal is a freelance business journalist and content marketer with a wide range of writing credits for various business and trade publications. In addition to freelance writing for trade journals and publications, Grensing-Pophal does content marketing for Fortune 500 companies, small businesses and individuals on a wide range of subjects, from human resource management and employee relations, to marketing, technology, healthcare industry trends and more.