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9 Tricky Interview Questions (and How to Answer Them)

By Biron Clark


Today’s job candidates are as likely to be asked which superhero they’d prefer for a boss as they are to describe their greatest weakness. The substance of tough interview questions may change over time, but the aim remains the same: to trip up the applicant and see how they respond to the uncomfortable and the unexpected. Your interviewer is likely more interested in your demeanor as you answer the question than he/she is in your answer. So strategic use of pre-interview research is the key to feeling prepared for anything that might be asked of you.

Here are some strategies for answering nine of the toughest “trap door” interview questions.

9 Tricky Interview Questions (With Answers)

1. What are your weaknesses?

Do your research and be ready with an answer that plays to your best-educated guess of what the particular company is looking for in a new hire. Shape your answer into a story about how you’ve worked on one of your weaknesses and turned it into a growing strength. If you can tie this growing strength to one of the skills needed for the job you’re going after, you’ll really ace the answer to this question.

2. Why do you want to work here?

To answer this, or the closely related “What is your ideal work environment?” question, research the company’s mission statement as well as any positive news you can find about the company ahead of the interview. Try to weave specifics of both into your answer. For example, if the company has recently launched a new product, and you’re really jazzed about the roll-out of this product, mention this in your answer.

If you want more help with this, here’s a full article on answering “why do you want this job?”

3. Where do you see yourself in five years?

This tough interview question is often asked by employers who are looking for a sense of commitment from candidates. You need to answer in a way that makes clear that your goals align with the company’s and that you hope to grow in ways that align with the job you are currently seeking. This is a crucial interview question that you shouldn’t flub.

PS: if you don’t see yourself at the company you’re interviewing at in five years, don’t mention it! Focus instead on the type of role you want to be in five years down the road.

Further reading: In-depth guide to answering “where do you see yourself in 5 years?”

4. Why do you want to leave your current company?

Like the “Why did you leave your last job?” question, this question requires you to find an aspect of your current (or previous) company that you liked and that is also present in the company you are interviewing for, and then talk about it honestly. Emphasize what you were able to accomplish in your last role, how you were able to grow, and never speak negatively about a past employer.

To prepare yourself for this tough interview question, here’s a write-up on answering why you want to leave your current job.

5. Why is there a gap in your work history?

Be prepared to answer this question in a way that emphasizes how you’ve employed your professional skills during times of unemployment (this also should be noted on your resume or in your cover letter). If pressed, be honest about how and why you left past jobs, including dismissals, but do not fall into the trap of criticizing past employers. Simply emphasize the positive aspects of each past employment experience in ways that make clear how these past experiences will help you bring value to your next position.

Want more help with this? View our full guide on how to explain gaps in employment.

6. Tell me about a time you made a mistake

Questions about past mistakes are some of the toughest and trickiest interview questions to answer. You want to acknowledge the mistake (and never badmouth or blame others), but you never want to make yourself seem like a liability or a risk to hire for this new job! Avoid talking about mistakes involving carelessness or lack of effort. It’s better to talk about making a mistake because you hadn’t experienced a situation before, or didn’t quite have the right knowledge. And then here’s the key – at the end of your answer, talk about what you learned from the experience and how you’ve become better since then. If possible, talk about encountering a similar situation a second time and getting a much better outcome because of the lessons you learned.

If you want more help with this, here’s an article on answering “tell me about a time you failed.” 

7. What can you offer us that other candidates can’t?

This is another tough interview question because the interviewer is putting you on the spot to brag about yourself and sell them on why they should hire you. While this is a tricky interview question to answer, it’s also a big opportunity! This is your chance to show what you can do for them.  That’s essentially what they’re asking here – “Tell us what you can do for us!’ So always be ready to talk about this in an interview.

Study the job description, think about your own resume and experience, and prepare to highlight how your knowledge and skills will allow you to come in and succeed in this role. Make it clear that you are the candidate that can solve their problems by making sure you do the research to find out what those are (or might be), and tailor your answer to those issues with specific examples of how your skills and experience can be applied to those issues. Tell a success story about how you addressed similar issues in the past.

8. What did you like least about your last job?

If possible, mention a task that will not be required in the new role or work environment. Don’t focus on politics or people. Then, shift to what you liked about your last job, especially those parts that will also be part of your new role. It’s worth re-emphasizing this point: do not speak negatively about a past or current employer.

9. “What if” questions

These interview questions can range from “What would you do if you found out a coworker lied to a client?” to “If you could have a superpower what would it be?” Hypothetical questions often, even intentionally, have nothing to do with your area of expertise. That’s part of what makes them so tricky to answer. Some are designed to gauge your values, but more often they are simply presented to see how you handle a situation you are not expecting and cannot really prepare for. The interviewer wants to see how you think on your feet when asking a “what if?” question.

Don’t be afraid to respond to “what if” questions, or any question that makes you feel slightly uncomfortable, by expressing your surprise at the question, or asking for a moment to think through your response. Also, accept the challenge with a bit of mildly self-deprecating humor, and then launch into your answer. Humor will ease the tension—yours and your interviewer’s—and that always leaves a good impression.

Bonus question and answer: Tell me about yourself

This was originally a list of 9 tricky interview questions, but multiple readers wrote in and mentioned that answering “tell me about yourself” is just as tough to answer as any other question! When employers ask this, they typically want to hear about you as a professional. I recommend starting with how you began in your current industry or field of work. If you just graduated, talk about why you chose your major/field of study.  Then talk about some key accomplishments and work you’ve done recently.

Finally, conclude by sharing what you’re hoping to do next, why you’re applying for their position, etc.

Things to Keep in Mind When Answering Tricky/Tough Interview Questions

Interviewers love to ask tough questions that you’re not expecting. However, if you stay calm and composed and use the steps above, you’ll give great answers and get more job offers.

Here are 3 things to keep in mind that should help you further:

1. First, the interviewer is *not* out to get you. They want you to give good answers. They’re looking for someone they feel comfortable hiring! And they’d rather find that person sooner than later.

2. Next, it’s okay to say, “Hm, that’s a tough question, let me think for a minute.” No interviewer will fault you for doing this once or twice in an interview.

So don’t just blurt out an answer and rush yourself if you hear a tricky interview question that caught you completely off-guard. Take a deep breath and think it through.

3. And finally, for many of these questions, the interviewer just wants to hear your thought process.

We have a separate article with 8 tough brain-teaser interview questions asked by Google, Facebook, etc., and when an employer asks something like, “how many golf balls do you think could fit in a mid-sized sedan?”…  they really just want to see how you approach problems and think things through.

So this is why you should never panic and never be afraid to say, “let me think for a second”  when you’re asked a tricky interview question that you’re not sure how to answer.  If you take your time and remember that sometimes employers just want to hear how you think, you’ll ace the interview and survive any tough, unexpected questions they ask.

Biron Clark

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3 thoughts on “9 Tricky Interview Questions (and How to Answer Them)”

  1. Thanks, The information giving was very helpful and I would have been more prepared with my interview had I checked this site two days ago

  2. Oh , thank you so much , this topic helped me a lot , I will prepare myself to answer the listed questions , they’re not quite easy , but when you discover what It is , I think It becomes more easier to respond on it!
    Thank you LiveCareer.

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