How To Answer These 6 Tough Job Interview Questions

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Person interviewing for job.

This doesn’t look too intimidating, right?

Simple job interview questions sometimes lead to confusion and fumbles. So, it’s no surprise that tricky questions can catch even the most qualified job candidate off guard.

Below, I’ve outlined how to answer the toughest interview questions. Don’t let the simplicity of some of them fool you—you’d be surprised how many candidates can’t answer them correctly.


1. What’s One Thing You Would Change About Your Last Job?

Be careful when answering this question—many candidates take it too far.

Try your best to avoid trash talking old employers or former co-workers. As I’ve mentioned before, this makes you look like a loose cannon. Essentially, if you badmouth an employer, you bite the hand that fed you.

There may also be a follow-up question, like “Why didn’t you comment or try to do something about the problem?” Prepare an answer that doesn’t shed an unflattering light on yourself.

2. Why Should I Hire You?

This question lets the person interviewing you know whether you did your research before the interview. When I worked in recruiting, I was astounded by how many candidates had no idea what they applied to do!

Avoid this fumble by researching the company and the open position. Then, tailor your answers to fit what they are looking for. This is also a good time to toot your own horn. Own what a good candidate you are!

3. Why Is There A Gap In Your Employment History?

Employers understand that people lose jobs and sometimes can’t find another one so easily, but that’s no excuse for slacking off.

Tell employers about freelance projects, volunteering, or any classes that you spend your time on. Medical emergencies and taking care of family members are valid answers as well.

By answering this question properly, you show the employer that you were productive while you were unemployed.

4. What’s The Biggest Risk You’ve Ever Taken?

Skydiving is not a good answer. Neither is bungee jumping.

Instead, ensure your answer applies to the position you are interviewing for. If that role requires tenacity or quick thinking, prepare an example that shows how you excelled in such situations. It also helps if your risk turned out to be successful.

5. How Would You Explain [Complex Idea] To An Eight Year Old?

Being able to explain something in very basic terms shows the employer that you have a solid understanding of complex materials.

Odds are, the complex idea will be something related the job. Rely on your experience with the concept (whether it’s databases, mortgages, financial planning, technology, etc.) and answer confidently.

Also, keep your response short. None of your interview answers should be too long, but you especially don’t want to ramble here.

6. What Is Your Biggest Weakness?

Perhaps the most famous “tough” interview question.

To me, this remains a trick question. Your answer should include a weakness that isn’t a weakness for the company or the position. For instance, “I’m just such a hard worker that I’ll stay late hours. I sometimes don’t know when to stop working!” Or, say something you worked on in the past that the new job won’t require.

Are these weaknesses? Technically, yes. However, a company won’t fault you for working too hard and may not care if you “disliked managing budgets” if they’re not asking you to do that.


Remember: Employers are not trying to see you fail—they just want to make sure they have the right candidate for the job. By doing your research and preparing ahead of time, you can tell them exactly what they are looking for.

Have a tough interview question that tripped you up? Post it in the comments to get some ideas for answers. 

(Photo: Wikimedia)

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  1. Amber April 24, 2014 / 11:33 am

    More examples of good answers (like in the last example) would be incredibly helpful, instead of just listing what are not good answers. Thank you for the article!

  2. Anna April 24, 2014 / 11:42 am

    Could you give an example of a good answer to question number one (What’s One Thing You Would Change About Your Last Job?)? I’m always interested in hearing specific examples of what impressed a hiring manager.

    Thank you!

    • Ryan Lane April 25, 2014 / 9:34 am

      Thanks for writing, Anna!

      To me, the key part to this answer is where Amanda says to “not take it too far.” If you’re talking about something you wish had been different, it’s probably because you didn’t like the way things were done, right? So, keep those emotions in check and don’t make things personal.

      For instance, if communication was poor within your organization, don’t say something like, “My boss never told us what was going on … and acted like a real jerk when we tried to find out.” Instead, keep things high level. You might even be able to turn your response into a positive about yourself, like, “I really value open and clear communication, and I wish that had been better at my previous job.”

      Hope this helps!

  3. Claire April 24, 2014 / 1:33 pm

    For 6. What Is Your Biggest Weakness? most career consultants I know strongly suggest against interviewees using the “I’m just such a hard worker” line. Employers can see right through it- the response is disingenuous and unoriginal. it’s better to answer in an honest and constructive way, which would help make you stand out against the others who weren’t brave enough to say something real.

  4. Stacey April 25, 2014 / 4:59 am

    I must agree. You all tell the hard questions, but never help us with the answer. I see people in positions that don’t like there jobs, bad customer service, or don”t no there job. I feel I could do, but interviews don’t give me a chance. I would like a chance to win them over.

  5. Doris Anderson April 26, 2014 / 1:25 pm

    I totally agree with every one who has said that you tell us to give good answers to the hard questions, but you don’t tell us any good answers to say to the interviewers. For example, “why should I hire you” could you give us some examples? Or “what is your biggest weakness.” It would be really helpful if the experts on these questions would give good examples that people have used instead of just telling us what not to do. Thank you so much.

  6. Nunya April 29, 2014 / 2:29 pm

    Pretty useless. Supporting evidence for why it is never a good idea to read emails similar to the one from which I found this article.

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