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How to Answer the 3 Hardest Job Interview Questions

Topics: Career Advice

Let’s face it: when it comes to job interview questions, even the easiest can feel pretty tough. For one thing, you only have a limited period of time in which to make a good impression on the interviewer and find out what you need to know about the job. For another, unless you’re one of those rare souls who enjoys high-pressure situations like job interviews and first dates, you’re probably coping with a pretty serious case of nerves.

Still, some questions are harder than others, and we’re not just talking about the really weird ones, like, “If you were in a hot air balloon with several other people and it developed a puncture and was sinking and going to crash and somebody had to be chucked out to lighten it, how would you convince everybody it shouldn’t be you?” (An actual job interview question asked of one Redditor.)

No, in fact, the hardest job interview questions to answer are pretty simple on their face – they’re just a great opportunity to blow the interview before you even really get started.

hardest job interview questions

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  1. Tell me about yourself.

Technically, this one isn’t a question, but it’s still a pit full of quicksand, waiting to suck you down. Honestly, this one should be considered cheating, since it requires almost nothing of the hiring manager, and gives you almost nothing to go on as a candidate. Is the interviewer looking for your entire history in 60 seconds or less, or a sense of who you are as a person, or an idea of how you’d solve the company’s problems and/or spur the organization to even greater heights of success?

In short, yes. This is where having your elevator pitch honed and ready to go is so important. Ultimately, a job interview is your chance to sell yourself, as well as to find out if this gig is a good move for you.

“A formula I really like to use is called the Present-Past-Future formula,” says Kathryn Minshew at The Muse. “So, first you start with the present—where you are right now. Then, segue into the past—a little bit about the experiences you’ve had and the skills you gained at the previous position. Finally, finish with the future—why you are really excited for this particular opportunity.”

  1. What are your salary requirements?

First of all, if you can avoid answering this interview question, it might be in your best interests to do so. (And here’s five ways to do that, in case you’re feeling stuck.)

Sometimes, however, you’re going to have to come up with a number, either for your salary requirements or your salary history. Salary history is obviously easier, because you know that you shouldn’t lie. (Because liars get caught, and wind up embarrassed and unemployed.) But it’s also tougher to deal with from a salary negotiation perspective, because it potentially boxes you in.

For this reason, whether you’re asked to give your salary history or your salary requirements, your approach should be the same: come to the table with information on what this position should pay, based on the job requirements, your experience and education, and the location. PayScale’s Salary Survey can help you set a range that’s appropriate to the role.

Then, if the hiring manager tries to peg your offer to your job history, not the job title in question, take inspiration from Penelope Trunk’s sample script in PayScale’s Salary Negotiation Guide, “This position is not exactly the same as my last job. So let’s discuss what my responsibilities would be here and then determine a fair salary for this job.”

  1. Why were you fired?

This is maybe the toughest question to hear during a job interview, regardless of how you lost your job – but the circumstances of the termination will inform how you answer.

If you were laid off, your task is pretty easy. Just give a brief mention of the restructuring, and refrain from badmouthing your former employer (essential, no matter what the situation).

If you were fired, coming up with an answer is a bit harder. The goal is to give an answer that’s honest, reflects well on you (by showing that you’re self-aware and have learned something from the experience, for example), and that moves the conversation forward.

Alison Doyle at’s Job Searching site gives several good examples of scripts that might work, including:

“After thinking about why I left, I realize I should have done some things differently. That job was a learning experience and I think I’m wiser now. I’d like the chance to prove that to you.”

Your answer will vary, depending on your experience and situation. The most important thing is to be prepared with an answer that explains what happened while casting you in a positive light.

Tell Us What You Think

What’s the hardest question you’ve ever been asked in a job interview? Tell us about it in the comments, or join the conversation on Twitter.


Jen Hubley Luckwaldt
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Donkey Dramastic
Donkey Dramastic

Hardest question – as an opener, too! – “Why should I give you the job?”

In leaving this comment, I got told “input is too short”. My result echoes Polonius: “Brevity is the soul of wit.”

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