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Women in Focus

Difficult job interview questions and how to answer them

Stephanie Ashley
by Stephanie Ashley Published on December 13, 2013

Waiting for an interview can make anyone nervous. After all, a job interview is arguably the most important part of the hiring process. So, how can you prepare to blow your interviewer away? Start by preparing the perfect answers to some of the most difficult job interview questions. Preparation is key to your success!

The interview process can be the most nerve-racking aspect of the job hunt. You've made it to interview which is great, but now it's your opportunity to make the right impression. Once you've got your perfect outfit, know where you're going and done your research you should be good to go. But don't overlook preparing for those uncomfortably difficult questions, the moment you do they'll inevitably pop up during the interview.

We talked to Vicky Oliver, author of 301 Smart Answers to Tough Interview Questions and several other books on job-hunting, business etiquette and office politics.

Vicky was formerly in the advertising business, where she helped to interview and hire job candidates. She's shared with us some of the most challenging questions you might come across at interview and the most diplomatic ways to answer them.

There'll be no such thing as a difficult interview question when you've mastered these answers!​

1. What are your strengths and weaknesses?

The first part of this question is almost a no-brainer: list off your most promising attributes in a humble yet flattering light. To back up your claims, provide a few case studies of your best work.

The second half of the question, however, can be tricky. How do you tell an interviewer your weaknesses without them seeing it as a clear reason not to hire you?

Vicky gives us a very simple answer: “You want to frame everything in the most positive light.”

This means, while you should be honest about your weaknesses and shortcomings, frame them in a way that makes you look strong. In other words, tell the interviewer that while this may have been or still be a weakness for you, there are valuable things you have learned by struggling and overcoming your weaknesses.

2. Why should we hire you?

Think about this question before you attend your interview, because more likely than not, it will be asked. Vicky recommends that you do your research.

“You always want to Google the interviewer on the other side,” Vicky says. “Try to figure out that person’s philosophy as much as you can before going in there.”

Once you give yourself a good idea what your interviewer is looking for in the ideal candidate, use your strengths and case studies of your good work to prove how you fit into this ideal.

You should be able to show that not only you are a good fit for the company but that you're going to excel in the role and can bring something original to it too. Tease them a bit with what you would do within the role and indicate, through your previous success and experience, that hiring you would be a no-brainer decision.

3. I see you’ve been out of work, what have you been doing with your time?

If you have any large gaps of time in your resume, the interviewer will likely ask what you’ve been doing with yourself.

For some mothers, you may have been taking time off to be with your family or raise your children. For others, like college students, the limited job pool has made your job hunt take a little longer than expected.

Vicky warns you, though, not to be too blunt about your time off; once again, frame yourself in the best way possible.

“It’s not a good idea to basically say, ‘I’ve been looking for a job,’” Vicky says. “You have to prove that you have been burnishing your skills, polishing them while you have been looking for a job.”

To do this, during your time off, set yourself up for success. Vicky suggests, “Maybe take a class, take a public speaking course, join Toastmasters, or maybe do some community service work.”

Have something to talk about from your period of being away from the workplace and explain the new skills and experiences you've gained outside of work. If you've acquired transferable skills through your community work or part-time course, then share it. Your interviewer wants to know you're an engaging and interesting individual, not that you've been sat at home getting depressed with your job hunt.

4. If I called your former boss, what would he or she say about you?

This question can be a minefield for those who perhaps left their previous job under less than ideal circumstances. Vicky advises that, in an attempt to avoid this type of question, make sure you get written references from your previous job before you leave.

However, this will not keep someone from calling up your former boss. Vicky tells us, you need to play it cool.

“You don’t ever want to badmouth a person you worked with or for,” Vicky says, “but say what you learned from that. It is a good idea to talk about the environment, but not specific people.”

Even if you had a horrible boss, don’t be crass about your experience or this could make your interviewer think twice about you.

“You always want to say what you learned because a lot of times it gets back to the person,” Vicky says. “If you are positive, the whole search goes much better.”

5. Why did you lose your last job?

This last question is loaded. You don’t want to tell the interviewer that you were simply laid off or that you and your boss were at each other’s throats, but you do need to be honest.

Vicky says, in this situation, you must be extremely diplomatic. “You have to create a way to explain it that is accurate but also positions you in a positive light,” she says. “This involves telling the truth, but in the most glowing way you can.”

So, while you may have left your last job in a huff or frenzy, take the time to think about the positive aspects of the job.

“What did you learn from the experience?,” Vicky says. “What are you bringing forward from this with you? What skills have you taken from your experience?”

If you can frame yourself in the best light, as someone who, despite small setbacks, has come through with even more to offer, your interviewer will appreciate your positive attitude and optimism.

Don't forget

Interviews are tricky no matter how you look at it, but Vicky provides some encouragement by saying that, as with most things, practice makes perfect.

“It’s one of those things where the more you do it, the better you become,” she says. “That’s really unfortunate, because interviews are really difficult, and we all want to be really good at them the first time around.”

One way to become a whiz at interviews is to do as Vicky suggests and do a self-evaluation after each interview.

“Take notes the minute you can get out of the office building,” she suggests. “Sit down and determine how it really went. If it went smashingly well, you can use that in a follow-up with the interviewer. If it didn't go well, you can learn from that and do better the next time.”

With those notes, you can prepare yourself to do an even better job in the next interview you face. Prepare yourself appropriately before an interview by researching your interviewer and anticipating difficult questions, and you will be setting yourself up to make a glowing first impression.

For more tips on how to prepare for tough questions in an interview, check out Vicky Oliver’s book 301 Smart Answers to Tough Interview Questions.

Tell us, what are the toughest interview questions you’ve ever been asked? Tweet us @wewomenCA.

by Stephanie Ashley

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