The Most Challenging Interview Questions We’ve Seen (And Some of the Best Answers)

Interview questions can run the gamut. You've got your oddball questions: What clique did you belong to in high school? The too personal questions that tread into dangerous legal territory: Are you married? And the fair game, but hard-to-answer questions: Where do you see yourself in five years?

The Most Challenging Interview Questions

Trying to figure out how to answer them can definitely make your palms sweat. Below is a sampling of some of the toughest ones we’ve seen and some potential answers that may help.  

Were you fired? This is the king of the dreaded and difficult questions if you were, indeed, fired from your last job. Prepare an answer ahead of time. Think carefully about what happened and how to explain it. Answer the question honestly, but don’t provide any more information than you absolutely have to. One way to respond is to say your skill set wasn’t a good match for the company’s needs. If the mismatch was due to a corporate reorganization, for example, it’s okay to put it into context. But avoid bad mouthing your former employer—the only person it makes look bad is you.

Why should I hire you? This is a basic interview question that might make you feel defensive depending on the interviewer's tone, says Vicky Oliver, author of the book, “301 Smart Answers to Tough Interview Questions.” Don't let it rattle you. Instead, take a deep breath and stay calm. It’s an opportunity to sell yourself, so you should have a mental checklist of points you want to highlight. Practice your answer and be specific, whenever possible, about what you can bring to the organization. For example, if you know the company is in the process of moving over to new computer system, talk about how your skills and experience will help the company make the transition.

What’s your biggest flaw? If an interviewer asks about your biggest flaw, it's probably not the best idea to roll out a clichéd response like: "I work too hard," or "I'm a perfectionist." That's what everyone says, which will make the interviewer yawn, and won't help you stand out. Instead, talk about a challenge you faced and overcame. For example, "I used to have a fear of public speaking, but I attended classes to overcome it." But avoid bringing up weaknesses that would affect your ability to do the job, such as, “I'm horrible about meeting deadlines,” when the job would require you to meet them regularly.

What are your salary requirements? Talking about money is always awkward, but in this instance, you also have to worry about underselling yourself or pricing yourself out of a job. Your answer should really depend on the timing of the question. If salary comes up early in the discussion, the interviewer is probably using it as a screening tool to eliminate people, says Oliver. Don’t answer directly. “Say, my salary requirements are average for this position,” she says. If the question is asked at the end of the interview, it could be an indication they like you. Try to find out the salary range for the position ahead of time whenever possible; this can help you provide a reasonable figure.

What’s your favorite song lyric? Would you rather fight 1 horse-sized duck, or 100 duck-sized horses? What would you do if you found a penguin in the freezer? There’s really no end to the crazy, oddball questions an interviewer may throw your way. The good news is that when it comes to these questions there really is no right answer. The bad news is that you’ll have to figure out what on earth to say.

The interviewer wants to see if you can think on your feet and get a glimpse of your personality. "The behavioral and open-ended questions can be a bit more challenging because it's harder to prepare for the unexpected," say career and job-search coaching team Donna Sweidan and Tava Auslan, of The key is to think about what the interviewer wants to know—what they're really asking. For example, if the interviewer asks what type of tree you would be, he or she might really want to learn more about your personality traits. Before the interview, pull together a list of positive traits and accomplishments you want to highlight, and draw from that list. And don’t be afraid to throw in a little humor, these questions aren’t serious and provide an opportunity to let your personality shine through.

Ultimately the only way to figure out answers to all the toughest interview questions is to practice. The Internet is a treasure trove of information of information from the strangest questions ever asked to the traditional ones you can expect in most interviews. Practice mock interviews with a friend and also videotape the sessions so you can get a better idea of what others see and how you can edit your responses to be more clear and concise.

Preparing ahead of time and having clear ideas about what you want to convey in the interview can help you navigate even the most challenging questions, and help you answer them in a way that reflects who you are and what you can bring to the position.

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