By: Contributor On: January 24, 2011 In: Internships, Jobs Comments: 0

When you’re looking for a job, don’t be caught off guard by what we consider some of the hardest interview questions.

Avoid blunders with thorough preparation.

By following basic interview tips and anticipating some of the hardest interview questions in advance, you can avoid that heart-pounding, sweaty-palmed “uh-oh” moment of stumbling through an answer to a tricky question.

1. Why did you get fired from a job?

First of all, if you got fired, don’t bother trying to hide it. Nine times out of ten, your employer will find out – there are companies that exist solely for the purpose of checking the accuracy of people’s resumes. (I know because my friend worked for one — and caught some major resume lies.)

Though this is one of the hardest interview questions you’ll likely be asked, be upfront: did you miss too many days or constantly show up late? Explain that you had scheduling problems but have since learned to manage your time better. Whatever the reason, own up to it and demonstrate how you’ve learned from — and won’t repeat — former mistakes.

2. How was your relationship with your supervisor/boss?

Again, be honest but use diplomatic language. Never trash-talk a former supervisor/boss to a potential employer; this just makes you look immature and unprofessional. Highlight the positive aspects of the relationship — you can have a boss you hated (don’t say that) but who still taught you a lot (say that!).

3. As a professional, do you have any disappointments?

This is one of the hardest interview questions, but it also provides a great opportunity to highlight all sorts of positive traits — growth, maturity, motivation, ambition and more. If you messed up a previous opportunity (for example, passing on a job in another city in order to stay with a loved one) and regret it, now is the time to move forward: recognize your previous mistakes, explain how they changed you and point to the positive outcome (i.e., now you are at a point where you put your career before relationships).

4. What do you look for in a boss?

The hardest interview questions, like this one, are asking you to be honest — but professional at the same time. Yes, a boss can be an inspiration or a mentor, but don’t expect your boss to be your best friend. The most valuable bosses can be the toughest: the ones who motivate and push you to do your best. Your boss doesn’t have to be sweet and friendly, but there’s no harm in saying you look for a boss who is fair and receptive to employees’ needs.

5. What do you know about this company?

This will only be one of the hardest interview questions you get asked if you allow it to be. The best way to prepare for your job interview — and this question — is simply to do your research. Find out about the company’s history, who the key players are (and their backgrounds), what sort of work the company does (e.g., who some major clients are) and whatever else might be relevant.

If you really want to be prepared, memorize essential information about the company. Make flashcards and quiz yourself if you have to. It can only help you in the interview.

6. Why do you want to work for this company?

Again, getting this one right is all about doing your research. Pinpoint specific things about the company that you like. From their corporate philosophy to the clients they work with, there must be something that you can find about the company that appeals to you and makes it stand out from other companies in the same field.

7. What’s your greatest weakness as a professional?

This one is hard because it’s so common, meaning that everyone prepares for this interview question and tends to fall back on the clichéd responses that sound good but are actually duds: “I’m a workaholic” and “I can be obsessive about details” are the types of faux “weaknesses” that will simply make seasoned HR professionals roll their eyes.

Pick a legitimate weakness (for instance, your disorganization), but point to how you are improving (you started setting aside 15 minutes at the start of every work day just to clean your desk and schedule your day). This honest response will go over better than a non-answer that every HR rep has heard hundreds of times before.

Though these may seem tough, the hardest interview questions are usually ones you can actually prepare for in advance — so get going!

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