3 Tricky Interview Questions and How to Answer Them

November 30, 2016

Most interview questions are straightforward and are designed to find out what you know, such as “Why are you interested in our company?” or “Tell me about your experience in marketing.” But some interview questions are tricky in that that they aim to assess how you might act in difficult or high-pressure workplace situations. These questions are hard to prepare for and even harder to answer, so we’ve compiled some tips to help you deal with three of the trickiest ones.

1. Tell us about a time you failed.

This question might make you nervous, because it’s uncomfortable to discuss flat-out failure, especially when you are trying to impress an employer. The good news is that your interviewer is probably not interested in what you failed at doing, but rather how you responded to the situation. The first step to answering this question is to admit to having failed at something, which many people find hard to do. Second, you should articulate what you learned from the experience. You want to show not only that you reflected on what you did wrong, but also that you adopted feedback to ensure you would not make the same mistake again—both of which are admirable qualities that employers seek in job candidates. Third, make sure to communicate the steps you took to overcome your failure, whether you studied twice as hard in order to pass a test, or applied for three more research grants to successfully receive one. The goal is to take a negative experience you had and demonstrate how you turned it into a positive one.

2. Can you describe a time when you had to work with a difficult person?

While it may be tempting to denigrate a former co-worker or group-project partner in your answer, this is exactly what you should not do. With this question, your interviewer wants to understand how you work with others, to see whether you surmount challenging work dynamics or flounder under them. In your answer, do not focus on what the other person did wrong, but rather on what you did to overcome the issue in order to successfully complete the task at hand. Whether that was setting up meetings to hold a procrastinating co-worker accountable for making deadlines, or agreeing to compromise on an issue to manage differing viewpoints, you should aim to demonstrate your willingness to take the initiative and your ability to work well on a team.

3. What animal would you be and why?

Even though you may laugh off this question, many interviewers ask it in order to see how candidates respond under pressure. The aim of an “out of the blue” question like this is to see how you react to the unexpected—whether you can develop a creative answer on the spot, or whether you become flustered. For this particular question, the interviewer is probably not interested in the actual animal you identify as, but rather the characteristics you choose to describe yourself. For example, if you select a dolphin, you could emphasize your energetic personality and affinity for working with others. If you choose a bear, you might discuss your strong leadership skills and ability to be aggressive when accomplishing tasks. Instead of faltering at this question, use it as an opportunity to highlight some of your strengths in the workplace.

by Isabel Sperry

Chicago skyline from the beach
  • “Chicago Legal Search was very thorough about asking the right questions so that they could better understand the requirements of the position we were looking to fill. As a result, there was no time wasted in interviewing candidates that did not have the background or experience we were looking for, and in no time we had one of the candidates working with us. Chicago Legal Search was not only thorough upfront, but they remained actively involved throughout the entire process. Without a doubt, if we ever have the need to fill another position in this field our first call will definitely go to Chicago Legal Search.”

    Norma Jean Valadez, SVP/Managing Director of Accounting

    Edelman