10 Toughest Job Interview Questions (and How to Answer Them)

Woman being interviewed for a job
Job interviews aren’t easy. | iStock.com

You’ve toiled for months, sending dozens of resumes and cover letters, and your hard work has finally paid off. You got the job interview and now it’s time to prepare for your big day. You have a killer suit picked out, your hair is perfect, and you know everything there is to know about the company. There’s some good news and bad news. The good news: You’re going to look really good and sound knowledgeable. The bad news: It’s not enough to look good and be able to recite company facts. Your interviewer is likely preparing some difficult interview questions in an effort to weed out the best from the worst.
Career counselor Thomas J. Denham advises being prepared by practicing some common questions and answers beforehand.

The purpose of an interviewer asking you questions is to evaluate: 1) How prepared and motivated are you for this job with this company? and 2) How would you fit in with this company/department? Prepare a brief statement about yourself and say it over and over, so you get used to talking about your strengths in a succinct way. However, memorizing your answers will sound too “canned.”

How can you demonstrate you’re the right person for the job? Here are 10 of the toughest interview questions you’ll face and tips for how to best answer them.

1. What is your greatest weakness?

Woman lifting weights and working on her shoulders
Show how you overcame a weakness. | iStock.com/SolisImages

This is an interviewer favorite because your answer can help uncover flaws that may help the interviewer come to the conclusion you’re not the right person for the job. Career coach Mike Simpson refers to this as an “onion question” partly due to the question’s layers of complexity and the variety of ways it can be answered.

An onion question is a question with multiple layers … just like, well … an onion! And like an onion it can make you cry, but only if you tackle it unprepared. First off, this isn’t a simple question you can rattle off a quick answer to or parrot back some easy-to-memorize statistics or facts and move on. It’s a question meant to make you think, and think hard.

Simpson advises resisting the urge to deny you have any weaknesses. He says this is a slick way to avoid answering the question, and interviewers will see right through this tactic. Instead, Simpson recommends mentioning a real weakness that you’ve learned to overcome and are working toward overcoming. However, make sure the weakness is minor enough not to raise red flags and that it’s a problem that actually has a solution.

2. Why should we hire you?

Man interviewing job candidate
Be prepared for this question. | iStock.com

This question will likely catch you off guard. The key is to know exactly why you’re the best pick. Answering this question will require a delicate balance. The goal is to communicate confidence without sounding conceited. You also don’t want to appear to be begging for the job. “Every organization has a specific set of qualities that the potential hire needs to have in order to be successful in the position. It’s up to you to demonstrate that you have these qualities, and the most important place to do this is in your answers to the interview questions,” said Simpson. He continued:

Chances are you are going up against a group of candidates that all have very similar skills and experience.  The trick is to set yourself apart, and you can do this by highlighting a unique trait that you have that will contribute positively to the position. For example, everyone who is competing for an administrative assistant role will have experience with answering phones, word processing and filing. But let’s say you also had some project management experience. You could really emphasize your elevated skill at maintaining schedules and calendars, delegating tasks, and making deadlines. This little emphasis could really set you apart from the other candidates and leave you as a front-runner for the position.

3. Tell me about yourself

The Office
Market yourself. | NBC

Interviewing expert Laura DeCarlo said this question might also be phrased as “What should I know about you?” or “What would you like me to know about you?” This question gives you an opportunity to explain why you are the most qualified candidate. It will be important for you to take a close look at the job description so you can make sure you’re clearly demonstrating how your skills align with what the employer seeks. Review your resume and speak about past experiences that show you have the skills necessary for the position.
“This is an opportunity to market yourself, presenting yourself as the solution (right candidate) for their problem (a job to fill),” said DeCarlo. “In the interview, tell them the things that emphasize how your accomplishments and experience make you an ideal candidate for the job you are seeking,” DeCarlo continued.

4. Where do you see yourself in 5 years?

Office Space
Show you plan for the future. | 20th Century Fox

Never say you don’t know where you see yourself in the future. This shows lack of planning and a general attitude of not caring about your career. Not having an answer also suggests you don’t plan to stay with the company very long if you’re hired. You should be able to communicate your career goals and how you plan to reach those goals. An employer wants to see how passionate you are, not only about the job, but also your chosen career.
Such a question measures your commitment to your future career,” said Ball State University professor and internship coordinator Sheryl Swingley. She added:

When you are hired, companies want to keep you as long as they can. It’s expensive to search for new talent … I know a newspaper editor who asks this question of every young journalist he interviews. If interviewees indicate they hope to go to law school or move into public relations or advertising/marketing in a few years, which a number of journalists do, he won’t hire them for a job — or an internship. He doesn’t want to waste his time training someone who doesn’t plan to stay in journalism — his chosen profession …Whoever is doing the hiring wants people who are committed to a lifelong career in their area of specialization.

5. Why do you want to work in this industry?

The Office on NBC
Have industry knowledge. | NBC

The answer to this question will reveal whether you’re just job hopping or if you’re truly invested in your career and working toward a specific goal. When answering this question, be able to explain your career path and what prompted you to continue along the particular path you chose. Lauren Crane, a sales recruiter at Betts Recruiting, said this answer will require you to be specific. “Taking experience from your previous position, or time at school, is an easy way to ground your answer. Knowing what type of environment you excel in can be a great reason as to why you are interested in an industry,” Crane told The Cheat Sheet. “Take the time before an interview to understand distinctly why you are interested in the position, the company, and the industry.”

6. Why have you changed jobs so frequently?

fired from job
Be honest. | iStock.com

Switching jobs every few months doesn’t look so great on your resume. However, if you have a good answer, you’ll be able to navigate this potential interview question with ease. When it comes to answering this question, your best bet is to be honest. Perhaps the company culture was a bad fit, one or two companies shut down, or you received a better offer soon after starting another job. Whatever happened, describe the situation in a positive light. Another option would be to omit some of these jobs from your resume. If the start and end dates on these jobs are very close, there will be no noticeable gaps.

7. Why is there a large gap in your experience?

Prepare to answer this. | iStock.com

If there are large gaps in your work history, you’ll need a good answer. Your interviewer is likely to notice this right away. Take this time to explain how you filled those gap years. For example, if you went back to school or chose to take on a volunteer opportunity, talk about how that experience has strengthened you not only in your personal life but also as an employee. Make a connection showing how your time off has helped bolster your professional skills.

8. Why did you leave your last job?

headache during work at the office
Never speak negatively. | iStock.com/gpointstudio

Unless you were laid off, answering this questions isn’t always simple. You’ll have to think of an honest way to answer this question without placing blame on your employer or looking entitled. Cheryl E. Palmer, certified career coach and founder of Call to Career, says candidates should also be careful not to offer an answer that leads to more questions.

The basic rule of thumb here is to never speak negatively about your previous employer. What you should say is that as human beings we all sometimes see the same situation differently, but you have learned from all the bosses that you have had. Even if you did not get along with your boss at all, you can still usually say something positive about what that person brought to the table.

9. Why are you interested in this position?

Office, employees, co-workers, computer
Show you’ve done your research. | NBC

You’ll need to be more creative than saying you wanted a change. Most job candidates want a change and that’s why they’re interviewing for a new job (unless they were fired or laid off). Instead, discuss the attributes of the organization that are important to you. Show that you did your research and tell your interviewer why you’re excited about working for the employer.  

10. Do you have any questions?

Thinking young woman looking up at many question marks
Always have questions. | iStock.com/SIphotography

This question sounds deceptively easy, but don’t be fooled. The worst thing you can do is say you don’t have any questions. The second-worst thing you can do is ask questions that show you’ve put very little thought into preparing for the interview or questions that are self-serving. Instead, ask questions about how you can contribute to the company’s success.
Barry Maher, founder of Barry Maher and Associates, told The Cheat Sheet that a job candidate should make sure questions focus less on what the company can do for him or her and more on what the candidate can do for the company. “I was involved in an interview recently where the first three questions from the applicant were, in order: ‘How much vacation time do I get? How long do I have to be here before I’m eligible for a vacation? How long before I start to accrue additional weeks of vacation?'” Maher said. “What had looked like a great applicant now looked like someone who couldn’t wait to get out of work.”
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