Difficult interview questions and the answers to get you hired

If you feel like the job interview process is a complex combination of mind games that are intended to leave you clueless as to how to answer tough interview questions, you couldn’t be more wrong.

Time is of the essence; employers want to hire someone yesterday. As such, they’re not into playing games. The typical interview questions they ask are designed to cut to the chase and give you the best chance to sell yourself to them.

Your challenge as a job seeker, therefore, is to anticipate tough interview questions and knock your answers out of the park.

To help kick-start your interview preparation, craft smart answers to these five common interview questions. Knowing how to respond can give you the edge you need to nab a job offer.

1. What can you tell me about yourself?

A lot of interviewers lead with this ice-breaker, says Pamela Skillings, career coach and co-founder of New York–based Big Interview, an online job-interview-training platform.

“The hiring manager is trying to ease into the interview and lighten the conversation, which can be a good thing for both sides,” she says. Still, “your answer sets the tone for the whole interview.”

Don’t flub your way through this harmless-sounding question. Focus. Determining what you want the hiring manager to know about you is a big part of how to get the job. Amy Wolfgang, CEO at Austin, Texas-based Wolfgang Career Coaching, recommends preparing an elevator pitch—a two- to three-minute summary of your skills and professional experience, where you focus on credentials that are directly related to the job that you’re interviewing for, Wolfgang says.

2. Why are you looking to leave your current job?

One thing to know about how to answer tough interview questions: Don't dwell on the negative. Naturally, employers will want to know what instigated your job search. Phrase your answer carefully, especially if you’re unhappy with your current job. (And let’s be honest: You probably wouldn’t be looking for a new job if you were happy with the one you have.)

Your other challenge: “You have to be very careful and diplomatic with your answer,” says Courtney Templin, president of JB Training Solutions, a Chicago-based career development firm Templin, adding “The last thing you want to do is badmouth your boss or employer.”

The key is to offer a positive explanation, regardless of whether you’re having a negative experience at your job. One approach: “I love my current job, but I’m looking to work for an organization that aligns more with the skills I want to develop.” Or, keep it simple. You can never go wrong by focusing on the exciting opportunities this new employer offers.

3. Why do you want to work here?

This question assesses cultural fit, which is a top priority for employers today, Wolfgang says. It’s important to companies, particularly from a financial perspective because if you get hired and decide to quit because the job or company isn’t a good fit, it’s going to cost the employer a significant amount of money and time to find your replacement. (Fact: The average cost-per-hire is a whopping $4,129, while the average time it takes to fill a given position is 42 days, according to a report from the Society for Human Resource Management.)

Your answer should reflect the company’s desired image. Do your homework by studying their website—paying special attention to the “about us” or “our mission” section—or reading Monster's company review site, where current and past workers give honest assessments of their employers. Once you have a good understanding of what matters to the company, Wolfgang recommends preparing this answer: “When I read through the core values of your company, what really resonated with me was [X, Y, and Z].”

4. Why do you want this job?

This question may seem like it’s identical to the previous one, but the difference is it’s not about cultural fit—it’s about the work itself. An employer wants to hear how qualified and passionate you are, and a can-do attitude will take you far.

“They want reassurance that you’re genuinely interested in the job and not just looking for a paycheck,” Templin says. “This is your opportunity to show why you’re perfect for the job.”

Before the interview, make sure you review the original job posting and check out the description of duties. Then, highlight your skills that connect to the day-to-day job responsibilities. (“I saw this job requires proficiency in Excel. Here’s how I’ve used Excel at my previous jobs.”) Also, talk about why you’re enthusiastic about the job specifically. (“What I love about this position is it’s hands-on with clients.”)

5. What’s your greatest weakness?

This can be a tricky one to answer, especially if your first inclination is to try to mask a strength as a weakness (e.g. “I can be too much of a perfectionist sometimes”), but hiring managers can see right through that.

It’s OK to talk about a skill or technical ability that needs improvement, but you need to be able to point to steps that you’re currently taking to improve it. (“I’m in the process of strengthening my SEO skills by taking an online course.”)

You have to also make sure your weakness doesn’t hinder your ability to perform the basic functions of the job, Templin says. For instance, if you’re applying for a bookkeeping job, you don’t want to point out your not-great math skills.

Emphasize that you don’t shy away from a challenge, and that you welcome ways to become a stronger employee to better serve your team. 

Knowing how to answer tough interview questions is just one part of the job search. Need some more help finding the right job? Join Monster for free today. As a member, you'll get interview insights, job search tips, and career advice sent directly to your inbox so you can get hired sooner rather than later.