Tough interview questions and answers

Going into any job interview, you know you’re going to get some tough questions.

Tough interview questions and answers

Don't get stumped by these tough interview questions.

It's a fact: Knowing how to answer the tough questions in a job interview in ways that are both honest and powerful can help you impress the interviewer and land the job. Basically, you need to be ready for anything.

While there are definitely some questions you’ll hear again and again, it is in your best interest to prepare for the especially tough interview questions. “The interview is an elimination process,” says Dr. Thomas J. Denham, a career counselor at Careers in Transition LLC in Colonie, New York. “The employer is trying to weed out those who are not the most worthy of the position.”

To help you out with your interview preparation, here are some of the best answers to some of the toughest interview questions you're likely to face. Be sure to practice your answers and tailor your experiences to the information interviewers need to hire you. With the right preparation, you can turn those tough job interview questions into softballs. 

What is your greatest weakness?

This question is a common one, but Eric Melniczek, a career advisor at HighPoint University Career & Internship Services, points out that interviewers rarely ask whether it is a current flaw. He suggests an answer to the weakness question along these lines:

“In the past, I was unable to meet set deadlines. However, several years ago, I developed a technique where I write down what I plan to accomplish every hour of every day during the workweek and how I spend my time. Over the years, I have noticed that my productivity has improved dramatically utilizing this method. In fact, my work supervisor recently complimented me in a staff meeting with a dozen of my peers for consistently exceeding team and individual expectations as well as managing my time well."

You’ve probably identified a weakness in anticipation of this question. A good answer that shows you’ve solved it can illustrate your problem-solving capabilities.

Tell me a little about yourself.

Always be prepared for this question, or you'll end up droning on and on. Make your answer short and sweet, like your elevator pitch. Also, feel free to get clarification from the interviewer: Any area you'd prefer to hear about? My education? Experience?

Generally, you want to tie your answer into a professional attribute or two. For example: "I work well with others," "My strong organizational skills end up making me the leader in most projects I'm on," or "I approach anything I do with gusto and put in 150 percent." Or if you're a great communicator, say so and state how that attribute has helped you in your career. It doesn't have to be a difficult question if you think of it as, "Tell me something great about yourself." But you should be prepared.

Tell me about a project you worked on that required heavy analytical thinking.

This is a behavioral interview question. The interviewer is asking you to demonstrate your competency. The only way an interviewer can determine if you have enough analytical horsepower is to hear an example of how you used your analytical skills to achieve a goal: What formal and informal analysis did you do? How did you structure the project? What obstacles did you run into, and how did you overcome them? Here's an option:

"In 2005, I was given project X with a 10-day deadline and goal Y. The goal was clear, but I had to figure out how to get there. So here is what I did (analysis/decisions/actions). The end result was ______."

Why do you want to leave your current position?

The interviewer wants to make sure you won't walk out after six months and that you'll be satisfied in your new position. You have greater market value when you are looking on your own terms. Prepare a positive response you are very comfortable with. Refer to fit, personality issues or new directions. Your goals and readiness for a new kind of role are generally safe terrain. Just be careful to emphasize benefits to the employer, not your personal aspirations.

Tread carefully. You don't want to bad-mouth your current employer or put yourself in a weaker negotiating position. You could say, "Actually, I'm happy doing what I am doing now. But recently I have been keeping my eyes open for other opportunities. I don't need to leave, but for the right opportunity, I would consider it. This opportunity seems to fit the criteria I set out."

Tell me about a time you faced an ethical dilemma.

The interviewer is looking for evidence of your high ethical standards and honesty. You might want to say you haven't had any ethical challenges, but we all have our ethics tested at some point. For example:

  • You discovered wrongdoing, or someone asked you to engage in a cover-up.
  • Your employer failed to deliver the full value and quality on products or services paid for by a client.
  • A colleague cut corners on a project.

Without naming names, describe the situation and how you dealt with it. The response may focus on you, or it may involve other people. Remember, your political acumen is being tested—sometimes the best action isn't blowing the whistle but taking care of the problem yourself.

Tell me about a time when you failed.

No one wins all the time, so the key here is to forthrightly discuss what you learned from a situation that went awry. The interviewer also may want to hear how you handled any resulting fallout.

Failure comes in different forms: taking the wrong action, omission, or not doing enough or taking action soon enough. Some failures are big; most are small. Tell a story that isn't a career killer but shows you learned something substantive. Perhaps you failed to trust your gut on a hire and the person didn't work out, or you didn't intervene early enough with a problem employee. Talk about the lesson you learned from the mistake.

Tell me about your worst boss.

It can be tempting to trash your former manager, but you need to find a way to put a positive spin on this answer. Leanne King, president and owner of SeeKing HR, suggests talking about what you learned from your worst boss:

“My worst boss ever taught me things like graciousness, the absolute need for technical competency and professional respect -- these are core characteristics to creating high performing teams and areas she may have chosen to improve upon. I learned through a series of very difficult situations that everything about business is personal -- personal to me and certainly personal to her. Speaking to others with kindness and compassion certainly can take you further in your career aspirations. I was inspired to support the people who work for me, raise them up to reach their potential and encourage them to seek greatness.”

How would you deal with a high-strung personality?

If asked a question that relates to how you'd deal with a difficult personality, answer and then ask why the interviewer is asking. It's best to find out early if you're interviewing for a job with a lunatic so you can quit pursuing it.

Tell me a story.

Huh? Before you launch into Alice in Wonderland, find out what kind of story the interviewer wants to hear. Asking for clarification shows you are thoughtful and won't go on wild goose chases in the office if difficult projects aren't spelled out for you in advance.

Once you learn the type of story requested, create your very short tale around a time that you accomplished something great. Keep it short and sweet, and remember: Always make yourself look good. Think of this as the interviewer, "What don't I know about you that I should?" or "What skills do you have that could make you do this job well?"

What didn’t you like about your last job?

The employer who asks this question could be looking for you to answer with something that would indicate a weakness of yours, once again in an attempt to eliminate you. So while it may be tempting to trash your boss or complain about the hours ("They expected me to be in at 8 a.m.!"), try answering with something like this: “I did not feel my responsibilities were challenging enough.” Then the employer will feel confident that you are ready for whatever they may throw at you.

What sort of salary are you looking for?

This is a hard one because you don’t want to undercut yourself, but you don’t want to price yourself out of range, says Elliot Lasson, executive director of Joblink of Maryland. Ideally, you’ve done some research into the position and know what’s reasonable, but Lasson says you can also ask for more information:

“That's a fair question. To answer it properly, I'd need to know more about the position responsibilities and benefits package. I am quite confident that knowing the reputation of the company, when the time comes, any offer you make will be competitive.”

Why should we choose you?

When they ask, "Why should we hire you?" Dave Popple, president of Corporate Insights Global, suggests taking the approach quarterback Johnny Manziel took with the Cleveland Browns:

“I applied for this job because this is the company I really want to work for, not because I needed a job. When someone comes to a company they really want to work for, they invest more of their energy and time into their career. You should choose me because I made this company my first choice.”

Where do you see yourself in five years?

This is a hard one, because it’s difficult to predict the future. Heather Beaven, CEO of the Florida Endowment Foundation for Florida's Graduates, suggests a forthright approach: “I am both purposeful and flexible so I never carve a path in stone. Instead, I try to be fully prepared to maximize any opportunity that comes my way.”

How do I rate as an interviewer?

Even if you think the interviewer belongs in the Clown Hall of Fame, don't voice an ounce of criticism. You could say it's been a tough interview (if it has), and that you hope you are providing enough information for the person to make an informed decision. You could toss this back at the interviewer and ask, "How well do you think I would fit the job?" But be careful—you might not like what the person has to say.

Get help with your answers

Sure, these job interview questions are difficult, but knowing what's in store gives you time to craft the types of answers that will really dazzle hiring managers. Could you use some help crafting answers to these and other job interview questions?  Join Monster today. As a member, you'll get interview insights, career advice, and job search tips sent directly to your inbox. Monster's expert insights can help you untangle the tricky questions ("Why do you want this job?") and get to the heart of what interviewers are hoping to hear you say. The more prepared you feel, the more you'll be able to confidently field any question thrown your way.