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Job Seekers: Be Prepared for “Out of the Box” Interview Questions

In the world of interviews, gone are the days when it was considered good practice to volley standard, run-of-the-mill questions and trite answers back and forth in an over-rehearsed manner. As a candidate, if you give a cliché answer without much thought behind it, you run the risk of striking out; likewise, employers could lose a great candidate or place a poor fit if they don’t put effort into the interviewing process. As a result, the interview is changing drastically, beginning with a widening range of potential—and often unexpected—questions. Today’s job market and the companies hiring within it are focused more than ever on cultural fit and the attraction and retention of top talent, so if you’re a job seeker who has yet to prepare for out-of-the-box interview questions, it’s time to start.

In fact, Mitch Rothschild, CEO of a healthcare services website called Vitals, expects candidates to drop their “interview face” the moment they sit down—and he has an arsenal of tricky questions designed to help them do so. Foregoing standard requests such as “tell me about yourself” for unconventional queries like “can you give me a tour of your life” and asking unexpected questions such as “what percentage of your life do you control” gives him an advantage in an interview that he holds invaluable: the opportunity to assess how a candidate thinks about and reacts to the world, their job, and their life.

“I want to know what they’re good at, what they love about it, and get them talking about their passion,” Rothschild said in an interview with the New York Times. “I also try to get a sense of whether they’re comfortable with change.”

However, Rothschild isn’t the only one. Many CEOs and hiring managers are now adopting this practice, in companies both big and small; amongst the most infamous in tricky, creative interviewing processes is Google, who has been known to ask questions such as “how much does the Empire State Building weigh?” Of course, there is no way to accurately answer this question, but the answer is often not what the interviewer is most focused on. When asking questions like this, the hiring manager is typically looking for a demonstration of stress management techniques, problem-solving skills, and an open-minded and flexible approach to the unexpected.

Unlike typical interview questions with a tricky twist, such as “why should I hire you?” and “where do you see yourself in five years,” there isn’t a structured way to prepare for these types of questions individually—which is exactly the point. However, you can prepare yourself for tricky questions in general by asking yourself a few things before the interview, and formulating some answers that can be bent to fit a variety of questions:

  • How would I briefly describe my life? (Creating an elevator pitch could help with questions that are variations of this, but be sure not to sound too rehearsed).
  • What strengths do I want the interviewer to identify immediately, and how can I best communicate them?
  • What are my weaknesses and how can I overcome/improve upon them?
  • How do I approach most challenges, and how can I improve upon that?
  • What are some notable stories from my past positions? From my personal life?

This last one is especially helpful for punctuating your interview answers; for example, if you were asked Rothschild’s question “what percentage of your life do you control,” you could give an estimated percentage and tell a brief story that backs it up. Since these questions are designed to assess how you think and react to stressful situations, most interviewers will want more than a one-word or yes/no answer.

Of course, the nature of these questions is that they’re unexpected, so even with ample preparation and practice, you could still be taken off guard. The best thing to do is expect the unexpected and remain calm when it inevitably appears. Take a moment to think through your answer before giving it, but don’t stall too long, and deliver it with confidence.

A great way to build the confidence you need in an interview is to thoroughly research the company beforehand so you know what they’re looking for, which we’ve developed a guide for here.

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