10 Toughest Interview Questions

1. Why is there a gap in your work history?

“Employers understand that people lose their jobs and it’s not always easy to find a new one fast,” says Susan Nethery, the director of student affairs marketing at Texas Christian University, who often advises recent grads on the interview process. When answering this question, list activities you’ve been doing during any period of unemployment. Freelance projects, volunteer work or taking care of family members all let the interviewer know that time off was spent productively.

2. Can you think of a recent problem in which old solutions wouldn’t work?

This question is seeking a creative answer. The interviewer is trying to identify how knowledgeable you are in today’s work place and what new creative ideas you have to solving problems. Ex: Your workplace swears by fax machines for signing contracts. Until the phone lines go down. Did you save the day with a scanner and an emailable .pdf? You may want to explore new technology or methods within your industry to be prepared for. Twitter-phobes, get tweeting. Stat.

3. What would the person who likes you least in the world say about you?

“The people who can’t answer this question are the people I worry most about,” says Jim Link, managing director of human resources at staffing firmRandstad. “I can honestly say I’ve never hired one of them.”

Link says that this tricky question, a twist on the “what’s your worst quality or weakness?” standby, often leads to pregnant pauses as the interviewee struggles to present an answer that won’t present them in a bad light. “I’m not saying answer it quickly, because you should definitely answer it thoroughly.” Highlight an aspect of your personality that could initially seem negative, but is ultimately a positive.  His example? Patience—or lack of it. “Used incorrectly this can be bad in a workplace. But always driving home deadlines can build your esteem as a leader.”

4. What is the biggest risk you’ve ever taken?

“Some roles require a high degree of tenacity and the ability to pick yourself up after getting knocked down,” says Dale Austin, director of career services at Michigan’s Hope College. Providing examples of your willingness to take risks is important because it not only shows your ability to fail and rebound, but also your ability to make risky or controversial moves that succeed.

5. Have you ever had a supervisor challenge your behavior? How, and how did you manage that?

Pappalardo shares an anecdote from an interview he recently conducted. “The head of IT was rolling out a new technology to the sales team that required two days of training. He wouldn’t back down despite sales pushing back saying they couldn’t make time for it. Finally the president of the company challenged him about his actions, forced him to rethink his stance. He was a senior executive standing on propriety, not creativity.” In the end, Pappalardo says the executive rebounded and a compromise was reached—but it’s the lesson learned, not the situation, that the interviewer is looking for.

6. Describe a time when you were part of a project or planning team that could not agree…

Lynne Sarikas, director of the career center at Northeastern University’s business school, stresses that questions pertaining to difficulties in the past are a way for potential employers to anticipate your future behavior “by understanding how you behaved in the past and what you learned.” It’s important to clarify the situation succinctly, she says, to explain what specific action you took to come to a consensus with the group and describe the result of that action.

7. If you could change one thing about your last job, what would it be?

Beware oversharing or making disparaging comments about former coworkers or supervisors, as you never know what bridges you may be burning. But Taylor warns that an additional trouble point in answering this query is showing yourself to be someone who can’t vocalize their problems as soon as they arise. A good rule, she says, is to steer clear of people. Problems with technology are safe ground.

8. Explain a database in three sentences to your 8-year-old nephew.

This frequent Google question is no trick, and Taylor says it can be tailored to any sector. “Explaining public relations, explaining mortgages, explaining just about anything in terms an 8-year-old can understand shows the interviewer you have solid and adaptable understanding of what it is they do.” Do your homework, she says, “Know the industry and be well-versed.”

9. Tell me about yourself…

Seems simple, right?

It’s not. “This is difficult because people tend to meander through their whole resumes and mention personal or irrelevant information in answering,” says Dawn Chandler, professor of management at Cal Polytech’s business arm. Jana Fallon, a VP of staffing and recruitment for Prudential, agrees. “Keep your answer to a minute or two at most. Cover four topics: early years, education, work history, and recent career experience. Emphasize this last subject. Remember that this is likely to be a warm-up question. Don’t waste your best points on it.  Keep to your professional career!  (e.g., don’t cover your family life, weekend activities, pets, collections, etc.)

10. Why should we hire you?

The most overlooked question—and also the one most candidates are unprepared to answer. Chandler suggests that this is often because job applicants don’t do their homework on the position, and as a result aren’t able to pinpoint their own unique qualifications for the job. What they are really asking is why you are more qualified than everyone else. “You need to review the job description and qualifications very closely to identify the skills and knowledge that are critical to the position,” she says, “and then identify experiences from your past that demonstrate those skills and knowledge.”