25 smart answers to really tough job interview questions

Having smart answers to tough interview questions will impress your potential employer.

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Having smart answers to tough interview questions will impress your potential employer.
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Hajrudin Hodzic/Shutterstock

Some job interviewers ask tough questions designed to trick you. Others want to get a better sense of your thought process or see how you respond under pressure.

Whatever the reason, you’ll want to be prepared for curveballs or challenging questions.

In her book “301 Smart Answers to Tough Interview Questions,” Vicky Oliver says in order to prevail, you need to “trounce your competition.”

Read more: Here are the answers to job interview questions from 20 of America’s top companies, from candidates who know

Previous reporting from Business Insider’s Shana Lebowitz includes an ultimate guide to nailing any job interview. Lebowitz reported that speaking at a steady pace and resisting the urge to humblebrag are two key things experts recommend you keep in mind when answering questions.

We’ve highlighted 25 of the tougher questions you could be asked during your next interview, and examples on how to answer them from Oliver’s book, “301 Smart Answers to Tough Interview Questions.

It’s important to note that these sample responses are merely meant to help guide you. They won’t necessarily work for everyone, in every situation – and you should never lie in an interview.

Read on for the tough questions.

Vivian Giang contributed to a previous version of this article.


Q: What is your biggest weakness that’s really a weakness, and not a secret strength?

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Many interviewers ask questions about strengths and weaknesses.
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Tyler Bolken/flickr

A: I am extremely impatient. I expect my employees to prove themselves on the very first assignment. If they fail, my tendency is to stop delegating to them and start doing everything myself.

To compensate for my own weakness, however, I have started to really prep my people on exactly what will be expected of them.


Q: Will you be out to take my job?

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Questions like this are designed to be difficult.
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Joshua Vaughan/flickr

A: Maybe in about 20 years, but by then, I suspect you’ll be running the entire company and will need a good, loyal lieutenant to help you manage this department!


Q: You have changed careers before. Why should I let you experiment on my nickel?

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You may be asked questions about a time you changed jobs.
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Reuters

A: As a career-changer, I believe that I’m a better employee because I’ve gained a lot of diverse skills from moving around. These skills help me solve problems creatively.


Q: What if you work here for five years and don’t get promoted? Many of our employees don’t. Won’t you find it frustrating?

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Many employees become frustrated when they are not promoted.
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Allan Rotgers/flickr

A: I consider myself ambitious, but I’m also practical. As long as I am continuing to learn and grow within my position, I’ll be a happy camper. Different companies promote people at different rates, and I’m pretty confident that working for you will keep me motivated and mentally stimulated for several years to come.


Q: If you knew that things at your company were rocky, why didn’t you get out of the company sooner?

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You may be asked a variety of questions about your previous company.
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David Goehring/flickr

A: I was working so hard to keep my job while everyone around me was being cut that I didn’t have any time left over to look for another job. With all of the mergers that have been happening in our field, layoffs are a way of life. At least I gave it my best shot!


Q: I see from your resume that you worked at CC&L for four years, and that’s terrific. But I also noticed that you weren’t promoted during that time. Why not?

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Even if you work at a company for several years, promotions don’t always happen.
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PeopleImages/Getty Images

A: CC&L is a great company, and thanks in part to my team’s contributions, they are doing very well these days. But that wasn’t always the case.

During the first two years that I worked there, people were being fired left and right, and just hanging onto my job was a feat.

Once the company began to turn around, [my boss] was offered a terrific job at a rival organization and it took CC&L six months to replace him and when they did, the new boss was eager to bring in his own people. Once again, I tenaciously hung on to my job, and, even though I was long overdue for a promotion, I really didn’t think that the timing was right for me to broach it. No one from the old staff was there to even vouch for my performance!


Q: If you were running a company that produces X and the market was tanking for that product, what would you do?

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A frustrated trader.
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Reuters / Brendan McDermid

A: I would search for new markets for the product while I spurred the engineers to change the product to make it more marketable to its original core audience.


Q: From your resume, it looks like you were fired twice. How did that make you feel?

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Discussing a time you were fired can be a difficult question to answer.
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Mintybear/Shutterstock

A: After I recuperated from the shock both times, it made me feel stronger. It’s true that I was fired twice, but I managed to bounce back both times and land jobs that gave me more responsibility, paid me more money, and were at better firms.


Q: Are you telling me that, now that you’re 40-something, you would be willing to start at an entry-level position just to get your foot in the door here?

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Sometimes job changes are necessary to advance your career in the long run.
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Flickr/stevendepolo

A: Sometimes you need to take a step backward to move your career forward. Starting in an entry-level role would allow me to learn your business from the ground up.

The career that I’ve been in is so different than yours that I would love the opportunity to start over again in your field. The salary cut will be well worth it.


Q: You majored in philosophy. How did that prepare you for this career?

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Sometimes past training doesn’t always prepare us for current challenges.
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Márcio Cabral de Moura/flickr

A: Philosophy didn’t prepare me for a career in architecture at all. But it did force me to become philosophical about my prospects. After two years of trying to figure out what to do with my life, I visited Chicago one weekend, and was absolutely spellbound by the gorgeous architecture all around me.

I came home, applied to architecture schools all over the country, and was accepted by one of the best. I’ve never looked back … this is definitely the career that I was meant to be in.


Q: What are the biggest risks you’ve taken in recent years? Which ones worked out the best, and which ones failed?

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Failure is sometimes a result of taking risks.
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Flickr/jazbeck

A: I used to work at a large, global PR firm where life was sleepy, but comfortable. It was a “white-shoe” organization; people left every night at 6 p.m. and our clients were big biotechnology companies that really trusted the top management of our firm. After a couple of years went by, I felt like I wasn’t learning anything new, and I confess that I began to feel bored. I thought that if I took a job at a smaller PR firm, I would feel more challenged.

I joined a small PR boutique that had only been in business for five years. This turned out to be a colossal mistake. The top management was terribly unprofessional, plus they didn’t have the contacts with newspapers, TV, and cable stations that we really needed to service our clients properly. I canvassed my own contacts, of course, but I was the only person in the entire firm who had any contacts! Promises were made to clients that couldn’t be kept. It was a fiasco.

After six months, I called up the large, global PR firm and begged for my old job back. Fortunately, they hadn’t replaced me. They slapped by wrist for being disloyal, but they happily rehired me. I’ve been working there ever since, grateful, but bored … which is why I’m meeting with you today.


Q: What do you view as your risks and disadvantages with the position we are interviewing you for?

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Taking risks are also a part of applying to a new job.
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Donald Judge/flickr

A: I think that with the home office located halfway across the globe, there is a very small risk that one might not have the chance to interact with the key decision-makers as often as might be ideal. On the other hand, teleconferencing, email, faxing, and having a 24/7 work ethic will go a long way towards bridging the gap.


Q: From your resume, I notice that you interned at a small investment banking boutique. Did you pursue a full-time job offer with them? What happened?

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A woman transfers a phone call at a bank.
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Chip Somodevilla/Getty Images

A: Yes, I did very well at my internship, and I had originally assumed that I would come on staff once I graduated from college. However, BB&L drastically cut back the number of new hires they were planning. As fate would have it, they will not be hiring any of the interns they had last summer.

I love working at BB&L, and I brought some references with me today to show you that my job performance there was stellar. Still, in some ways, I consider this new turn of events to be a lucky break for me, believe it or not.


Q: Can you describe your dream job?

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Answering questions about your “dream job” can prove difficult.
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Strelka Institute for Media, Architecture and Design/flickr

A: This is my dream job and that’s why I approached you about it in the first place. I am excited about the prospect of helping your promotion agency upgrade and fine-tune your loyalty programs.


Q: Why did you take so much time off from work, and why do you wish to get a job now?

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Difficult questions can include, “Why did you take so much time off from work?”
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Alan Levine/flickr

A: When I first had the twins, my husband was working 24/7, and I really needed to be there to raise the kids. But during that time, I really missed working.

Fortunately, I kept my hand in the business during those years by consulting for several of my ex-clients.


Q: How many skis are rented each year?

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A man skiing.
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Doug Pensinger, Getty Images

A: There are 250 million people in the U.S. Let’s suppose that the number of skis is 15% of that, or 37,500,000. Of those, let’s figure that 21,175,000 of them own skis, leaving the number who rent at 9,325,000. Then let’s add the number of tourists who ski, say, 1 million. So the grand total of renters would be 10,325,000.

Now let’s assume that the renters who live here take three trips a year, so three times 9,325,000 is 27,975,000 and add that with 1 million is 28,975,000.


Q: If you were hiring someone for this position, what qualities would you look for?

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You may be asked about what qualities you would look for in a candidate if you were the hiring manager.
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University of Exeter/flickr

A: I would look for three main talents:

1. The ability to solve problems; 2. The ability to nurture strong working relationships; and 3. The ability to close deals.

A candidate who possesses all three would make the ideal associate new business director.

Let me tell you a little bit about my background …


Q: What would you do if you really wanted to hire a woman under you, and you knew the perfect candidate, but your boss really wanted to hire a man for the job?

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Difficult questions may include hypothetical scenarios.
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Intel Free Press/flickr

A: I’d recommend that we perform an on-site “test,” by hiring both candidates on a freelance basis for two weeks each.


Q: What if you worked with someone who managed to take credit for all your great ideas. How would you handle it?

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It can be frustrating if a coworker tries to take credit for your work.
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Getty Images

A: First, I would try to credit her publicly with the ideas that were hers. Sometimes, by being generous with credit, it spurs the other person to “return the favor.”

If that doesn’t solve it, I’d try to work out an arrangement where we each agreed to present the ideas that were our own to our bosses. If that doesn’t work, I would openly discuss the situation with her.

However, if the person taking credit for my ideas was my boss, I would tread cautiously. To some extent, I believe that my job is to make my superiors shine. If I were being rewarded for my ideas with raises and promotions, I would be happy.


Q: How many hours a week do you usually work, and why?

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Working long hours shows you are dedicated to your career.
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Flickr/hawker king

A: I work pretty long hours most of the time. With the extra time, I try to find ways to “add value” to each assignment, both my own and the firm’s. When our clients read our reports, I want them to think that no one else could have possibly written them, except for our company.


Q: Are you better at “managing up” or “managing down”?

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Managing is an important part of any job.
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innovate360/flickr

A: If you aren’t good at “managing up,” you rarely get the opportunity to “manage down.” Fortunately, I’ve always been quite good at self-management. I’ve never had a deadline that I didn’t meet.


Q: Please give an example of the most difficult political situation that you’ve dealt with on a job.

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Difficult situations sometimes arise at work.
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Daniel Goodman / Business Insider

A: I was hired by a woman who was on her way out. She asked me to be her “fall guy” on a number of assignments. I just learned to drop the assignments off with my boss on the day that they were due, and when the managers would ring me up, I would recommend that they simply follow up with her. This kept me out of hot water with my boss and with her superiors.


Q: Let’s discuss a time when you missed a significant deadline.

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Always meeting deadlines is a crucial part of any job.
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Monkey Business Images/Shutterstock

A: I would absolutely love to, but honestly, it’s never happened.


Q: Is it more important to be lucky or skillful?

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A four-leaf clover.
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Wikimedia Commons

A: I think that it’s more important to be lucky, although being very skilled can help to create more opportunities. Certainly, [at my former job, my boss’] confidence in me inspired the decision-makers at our firm to trust that I could do the job. But clearly, I also happened to be in the right place at the right time.


Q: When do you think you’ll peak in your career?

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You may be asked about “peaking” in your career.
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Daniel Goodman / Business Insider

A: I come from a long line of healthy, hardy, mentally active types, and so I confess that I never even think about “peaking” in my career. That having been said, I do think it’s important to have some self-knowledge, and to recognize when one is past one’s prime.