Many interview questions are boring, but they have to be asked. They can tell you a lot about the interviewee’s background, education, etc., but they tell you very little about his or her ability to think and act under pressure. If you want to test a potential employee’s critical thinking skills or simply want to determine if he or she would fit well in the work place, consider asking these tough questions.


Many of your interviewees will have come to you through job search engines. Either you found them and requested an interview or they found you and sent a resume. Either way, the standard questions have been asked and answer, which leaves room in the interview for you to be more creative. You have to be careful with oddball questions so as not to offend, but there are many ways you can go. Some common, out-of-the-box questions include asking the interviewee

  • what type of superhero he or she would be and why,
  • what type of fruit he or she would be and why, or
  • what state would he or she get rid of and why.

The goal with these questions is to see how the individual handles a curve ball. You are less interested in the details of the answer than you are in how fast the answer comes, how put off the individual is, and how creative the answer is. You also want to know if the person can deal with an unorthodox question with grace and maybe a bit of humour.


These questions often don’t have a good answer, at least not one that most people would know off hand. The answer is not what you are interested in, however. You are interested in how the interviewee goes about trying to get an answer. In other words, you are interested in the problem solving process and in how the person assesses the problem. Here are a few questions that have been asked in the past.

  • How many cows are in Canada?
  • How many quarters does it take to reach the height of the Empire State Building?
  • How would people communicate in a perfect world?


If you want to determine how self-aware a candidate is, then you need to ask them to assess their performance and other personal traits. Of course, you can’t just ask them to rate their abilities because they will simply rate them well-enough to please you without seeming overconfident. You will need to be more creative about quantifying performance, so here are a few ideas to get you started.

  • How would you rate your memory?
  • Tell me some time management mistakes you’ve made in the past
  • What do you think about when you are alone in your car?
  • On a scale of one to ten, rate me as an interviewer.

What these three questions share in common is an emphasis on honesty. If ethics, honest feedback, and independent thought are important to your business, then these questions can help you determine how candid of a person the interviewee is.


The point of these questions is to break the mould so that you can glean more information from an interviewee. They help you, in the limited time available for an interview, to assess the capabilities of the person sitting across from you. These questions are playful and humorous, but also serious and thought-provoking. In the end, your goal is to get to know a candidate before making an offer. These questions will help you do that.