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5 Application Questions That Are Tough To Answer

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You’ve polished your resume, identified which type of job you’d like to have and even picked out your interview outfit. But have you thought about how you’ll answer the most notoriously difficult job application questions?

Most employers require job applications as a screening tool, so it’s crucial that you go over the trickiest application questions and answers that you’re likely to encounter. Here are some tough application question examples that often pop up and how to answer them:

1. What is your biggest weakness? (No, we’re not asking about your secret strength.)

Most job applications ask a variation of the question, “What is your greatest weakness?” And while you may be tempted to dodge this question by sharing a supposed weakness that’s actually a desirable quality (for example, “I’m a really hard worker, and sometimes I just work way too hard!”), the person reviewing your application will see right through this approach. That’s because at this point, nearly all job candidates have thought to respond this way, so it’s become a rather cliched response.

So, how best to answer this question? Don’t turn your application into a therapy session by revealing your biggest, red flag-raising flaws, and don’t avoid the question. Instead, briefly describe a real weakness (one that wouldn’t be a major problem if you got the job) and discuss how you’re working to improve that weakness. The improvement part is the most important element here; employers want to know that you’re proactive and self-aware.

2. Why do you think you’re a good fit for this role?

This one can be a danger zone. You don’t want to come across as arrogant, of course, but you also want to demonstrate that you know your stuff and that you’re the best person possible for the position. Rather than rattling off a generic list of your best attributes (please don’t do this!), it’s best to come at this question from a problem-solving lens. Think: You already have done your research on the company and how they can improve, so focus on how you’re uniquely qualified to help them do this.

3. Why did you leave your last job?

If your last job ended because you had a problem with your boss or co-workers or you were fired, you may struggle with how to answer this question, especially if you have a big gap in your employment history. Honesty is the best policy here, though, and it’s possible to put a positive spin on the situation. For example, if you’ve been out of work for a while, you could talk about the meaningful volunteer activities you’ve been doing in that time, or you could discuss the adult education courses you’ve been taking to keep your skills fresh.

4. Why don’t you tell me a little bit about yourself?

This question is tough. When you hear it, you may be inclined to recount your entire life story... and that isn’t at all what your potential employer wants to hear. Your answer should be tailored to fit the job you’re applying for, so focus on the specific skills, anecdotes and life experiences that demonstrate your aptitude for the job.

5. Where do you see yourself in [x number of] years?

Ah, this can be one of the hardest application questions out there. (After all, who knows where they’ll be in six months, much less several years?) Your employer isn’t asking this question because they want to know if you think you’ll have kids or a house in the near future, though. They’re asking because they want to know whether you plan to stay with the company that long. So, don’t make the mistake of saying you want to go back to school for an unrelated field or start your own company; reassure your employer that you’re in it for the long haul, instead.


Justine Harrington is a writer based in Austin, Texas. Her work has been published in Forbes, USA Today, Fodor's, American Way, Marriott Bonvoy Traveler, Texas Highways, Austin Monthly, and dozens of other print and online publications.

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