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How to answer the 6 toughest job interview questions

Don't sweat the tough questions at your next job interview. (Daniel Fishel)

When she’s interviewing job candidates, Audrey Chang wants to get a sense of how they handle the challenges that inevitably arise in any workplace. So the senior vice president at Subject Matter, a D.C.-based advertising, government relations and communications firm, often asks a favorite question: Can you give me an example of a time when something didn’t go as planned and how you dealt with that?

“Everything has a plan, but we all know life doesn’t go according to plan,” she says. “We’re always confronted with things not going exactly the way you thought they would, and resilience is really important to me. To show that you can think beyond the ideal plan is something I’m looking for, that ability to react.”

Her query helps Chang determine if an applicant can handle stress and uncertainty. But job candidates aren’t often fans of tough interview questions like that. Even the best applicants can get tripped up by questions that delve into sensitive subject matter or are so broad that it’s hard to know where to begin.

Don’t let that happen to you. We asked experts for advice on how to answer some of the most dreaded job interview questions.

“Where do you see yourself in five years?”

You’re focused on landing the job for which you’re interviewing. But now you’re being asked about the future?

This question is all about assessing a candidate’s motivation. “Companies want to invest in people who have a self-interest in growing as well,” says Jason Patel, founder of D.C.-based college and career consulting firm Transizion. “If you’re working hard for yourself, you’re going to be working hard for the company.”

Patel advises structuring your answer around the goals of the position for which you’re applying. “If you can grow in that position and provide value for the company, you’ll be helping the company achieve its ultimate goals,” he says.

Don’t be afraid to take a broad approach to your answer. “My strategy for this question is a learning and growing strategy,” says Laura M. Labovich, CEO of the Career Strategy Group in Bethesda, which offers career and job search services. “Say, ‘My goal is I want to be here at this organization constantly making a difference doing work that I love and am challenged by.’”

“Tell me about yourself.”

This request can leave candidates looking like the proverbial deer in headlights, wondering how much of their life story the interviewer really wants to know. But you don’t have to start by telling them you were born in a small town — unless that’s relevant to the job on the table.

“If you’re interviewing for a Hill job and the [representative] is from a small town, that’s a connection to make,” says Chang. “It’s about making that connection to what they’re doing.”

Candidates often hate this open-ended query, but Labovich says they should be thankful for it. “This is an opportunity for you to have a platform,” she says. “It’s the longest time period an employer will ever give you to talk about yourself, so you need to use that platform in the best way.”

She advises picking two qualities you want to emphasize about yourself and then supporting them with examples. But know that you can’t devise just one standard answer to this request for every job interview you land.

“You will always need to tailor it to the company interviewing you to emphasize the qualities they are looking for,” says Labovich. “Your answer is never static.”

“What are your weaknesses?”

You want to put your best foot forward in a job interview, not talk about your flaws. But it’s far more likely you’ll be asked about the latter.

Avoid the inclination to go cute or cliche with your answer. “Don’t say, ‘I don’t have any weaknesses,’ because that shows a complete lack of self-awareness,” says Patel. “And don’t say, ‘I’m too much of a perfectionist,’ because that doesn’t give anyone anything.”

The key here is to talk about a real weakness you have (but not one that’s severe enough to knock you out of the running for the job) and then to address how you overcome that weakness.

“‘I don’t get along with people’ would not be something you’d want to share,” says Labovich. “But maybe you’re not terribly comfortable in front of a room. So you can talk about how you’re going to Toastmasters and finding ways to get out of your comfort zone as much as possible.”

“What did you dislike about your previous job?”

You may have a long list of responses to this question, and they might be the very reason why you’re looking for a new position. But you don’t want to spend your interview time trashing your current or former employer.

For this question, make sure you can spin any negatives you mention into positives. “Instead of saying, ‘My last boss didn’t let me do XYZ and I resent her for micromanaging me,’ say, ‘I’m looking for an opportunity that allows me to do XYZ and I’m looking for more autonomy so I can show my creativity in my work,’” says Patel. “Everything you answer with here should be geared toward the future and about how you want to better yourself and your next company.”

For Chang, this kind of question also speaks to how candidates deal with adversity. “If you had a bad experience at a job, briefly say whatever the issue was,” she says. “But as the interviewer, what I’m looking for is what you really learned from that experience.”

“What kind of pay are you looking for?”

This is a tricky question to answer. You don’t want to underprice yourself, but you also don’t want to throw out a number that’s completely unrealistic.

“The first person who mentions a number loses when it comes to negotiations,” says Bianca J. Jackson, a career coach based in Silver Spring. “So I would try to get a number from them first. Every position is budgeted, so I would flip the question back onto them: ‘What have you budgeted for the role?’ ”

Deflection is always a smart strategy. “Usually I’d say, ‘I’d love to learn more about this position before we discuss pay, and if this is the right role for me, I trust that we won’t let pay get in the way,’ ” says Labovich.

“Do you have any questions for me?”

When the interviewer gives you the chance to turn the tables, don’t let it go to waste. Patel suggests having at least three questions at the ready.

“My go-to questions are: ‘What are your clients’ biggest problems and how will this position I’m applying for help solve them,’ ‘What are the company or team goals over the next one to three years and how will I be able to help,’ and ‘How will this position enable me to grow and better myself as a professional,’ ” he says.

Questions like these can help the interviewee better understand the expectations of the role. “It’s like dating,” says Chang. “Both sides have to decide if this is a good fit.”