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How to Answer Crazy Interview Questions

Crazy Interview Questions

When preparing for an interview, there are some common questions that veterans can almost be assured will be asked. Questions like:

  • What is your greatest weakness/strength?

  • How do you work as a member of a team?

  • Why are you leaving the military?

We’ve covered these questions (and recommended responses) in previous posts. Here we take a look at the other end of the spectrum: crazy questions that you likely didn’t anticipate, and how to respond to them.

Chris Chancey is founder of Amplio Recruiting. “I have asked and heard of a number of seemingly crazy interview questions,” says Chancey. 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?

Here’s a look at how other recruiters have used crazy questions to ferret out details about applicants’ personalities and readiness for various jobs.


Why would an interviewer ask a question like: “What wild animal would you be and why?” According to Donna Shannon, president of Personal Touch Career Services, while it sounds silly, this type of question is designed to showcase your personality. “The actual animal you pick doesn’t matter,” she says. “It’s all about the reasons why.” For example, she says: “Choosing an eagle because they are able to see opportunities at a great distance, then swoop into quick action to make the most of the given situation shows that you have foresight and decisiveness.”


“What is your biggest regret and why?” This, says Jordan Wan, founder and CEO of recruiting firm CloserIQ, is not as crazy a question as it might initially seem. But, he says, “you’ll be surprised with the number of candidates who still get thrown off by this question.” When it’s asked, he says, hiring managers are looking for two things:

  • They want to see the candidate give an honest response

  • They want to see how they overcame this regret

If you’re asked this type of question, says Wan, it’s an opportunity to explain something that might be missing in your resume, or something that might look bad in your career. For example, he says, if you had a low GPA in college, this would be a good opportunity to explain that you regret not taking your coursework as seriously as you should have and how you’ve made up for this in other ways. “This shows the hiring manager that you’re honest and it can also clear any doubts about red flags in your resume,” he says.


In some cases, recruiters and other interviewers may ask purposefully antagonistic questions. Why? To get a sense of how well candidates do in stressful circumstances and how well they can keep their emotions in check.

Matthew Ross, co-owner and COO of RIZKNOWS and The Slumber Yard, says he has used this type of question with good results.

“My business partner and I tend to ask very intense questions during interviews,” Ross says. “We’ve interviewed multiple veterans and we always make sure to ask a question that goes something like this: ‘Looking over your resume, I’m not so sure you have the experience or skills to succeed here. Why do you think you would be a good fit?’ ” They purposefully frame the question in “a fierce manner” to see how candidates will respond, he says.

“Veterans have every right to be annoyed by the question given they’ve served our country. However, if they do get offended and lash out, then we know they probably wouldn’t be a good fit. If the person calmly responds with a succinct answer, then we know they are a solid candidate.”

Ross acknowledges that this approach may “seem cruel and make us out to sound like jerks,” but he says: “We’ve found this method to be very effective in weeding out temperamental and impulsive candidates.”


Sometimes employers are just being provocative or trying to trip up candidates. In other cases, though, they may have very good reasons to ask unusual questions, says Chancey. “They are most often looking for a spark of creativity or something that sets one applicant apart from the rest,” he says.

For veterans, he says, the ability to remain calm in stressful situations and answer difficult questions with confidence should be a given. But, he adds, “most employers still want to test you out, especially for positions in areas like crisis management or public relations.”

The important thing to remember, he says, is that there are no “right” answers. “The trick is simply to keep in mind the skills, personality traits and personal beliefs that are well-suited to the work in question.” And, he adds: “If all else fails, just be honest. Sincerity goes a long way.”


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