Top Ten Difficult Job Interview Questions And How To Answer Them

Are you smarter than an interviewer? If you prepare properly, you will be.
During a job interview, employers sometimes ask tricky questions to trip you up – not out of maliciousness but to get an accurate sense of your candidacy.

Interviewers know that you’ve probably practiced all of the traditional questions, so they try to stump you with trickier ones to get a better idea of your background, your communication skills, and how you’ll perform should they offer you the job.

Here are the 10 trickiest interview questions meant to trip you up, with suggestions on how to answer them and sample answers.

1. What’s your biggest weakness?

The Trap: The first step to fixing a problem is admitting it. When employers ask this question, it’s not just about figuring out your weaknesses, but about finding out whether or not you’re aware of them, and if you’re intending to make changes.
How to Answer: Be modest.

We all have weaknesses, and it’s okay to mention some parts of your skillset that need work. But, give your weakness a silver lining, and use your answer as an opportunity to highlight other strengths and underscore your determination to keep getting better.
Sample Answer: “I’m a perfectionist – sometimes to a fault.

While this means my work is always high-quality, I’ve realized that sometimes I spend more time obsessing over little details that don’t matter in the long-run, rather than moving on to my next task. I’m learning to work on prioritizing between perfectionism and efficiency, and learning about time management and productivity strategies.”

2. Is this position a similar role to any other jobs you are considering?

The Trap: Your interviewer may have two goals in mind here. He or she may be angling to uncover where else you’re applying or maybe trying to get a better idea of your past experience, and your future professional goals.

This can be a good way for interviewers to get a sense of your strongest skills and determine if you’ll actually be a good fit for the job.
How to Answer: If you’re applying for a variety of different positions, certainly don’t name them all – and don’t name-drop different companies. For one, you don’t want your employer to think that your skills and interests are totally all over the place.

Of course, it’s good to have a wide range of different abilities, but it’s most important to present yourself as the best fit for the specific job you’re applying for. For example, if you’re a writer who is also a project manager and you’re interviewing for project management jobs, you wouldn’t want to mention that you’re also applying to write jobs. Fortunately, this is the type of question where it’s acceptable to give a general answer and then move on.

Sample Answer: “Yes, I am looking for jobs that fit this description. This is my preferred field, which I’m personally and professionally passionate about. Fortunately, the job description, requirement, and responsibilities of this specific position seem best aligned with my experience and interests.”

3. Why do you want to work here?

The Trap: Employers want to figure out if you’ve done your research about the company, and whether you want this job, rather than any old job.
The Best Way to Answer: Don’t just say that you want to work there because there’s free gym access, complimentary coffee, and a casual dress code.

Make sure your answer has real meaning. Be enthusiastic in your answer and talk about how you connect with the company’s core values, its mission, and the work they do. Then, you can go into a little more detail about the specific position for which you’re applying.

Sample Answer: “I truly feel aligned with the company’s values, mission, and goals. I connect with your belief in integrity in your work, in fostering an open, honest and supportive workplace, and your desire to better the lives of both your employees and your customers. I believe that this position, specifically, will provide a huge – and enjoyable – opportunity for me to contribute to your objectives and add value to the company as a whole.”

4. If you could work for any company, where would you work?

The Trap: Your interviewer may be trying to figure out how invested you are in their company, in addition to determining where else you might be looking to apply. People sometimes have trouble answering this type of question. Because they can’t decide if they should keep mum, or mention some other, big-name companies that they’ve interviewed with.

The Best Way to Answer: Don’t mention any specific companies. Think about if you were on a date, and your date asks, “If you could date anyone else in this restaurant, who would it be?” If you asked your date that question, what would you want to hear? Emphasize how the company you’re interviewing with is your top priority.

Sample Answer: “Actually, I’ve spent a lot of time during my job search researching different companies I might want to work at, and this company stood out the most. I share your mission, values, and objectives and feel that I would really thrive in this type of work environment.”

5. Are you the type who checks email during your vacation?

The Trap: This is a tricky one. On one hand, you want to frame yourself as someone who is dedicated to their work. At the same time, employers know that employee health and wellness is a key factor to continued success and want to make sure you’re smart about taking care of yourself even outside of the office. Burn-out is a real thing, and no matter how durable you think you are, everyone is human and everyone needs a little rest sometimes.

How to Answer: Confirm your dedication to getting your job done, but also convey your understanding that personal well-being is key to professional success.

Sample Answer: “I’m 100% dedicated to going above and beyond when it comes to fulfilling my responsibilities. That being said, I also know that it’s important to take care of myself to ensure my long-term success. I try not to work when I’m on official vacation. But, before I leave for a vacation, I always make sure all my duties are covered before signing off, and I do make sure my supervisor has my personal cell phone number should an emergency arise.”

6. Where do you see yourself in five years?

The Trap: Employers don’t want to invest in hiring, training, and paying an employee who’s not going to stick around, or who’s going to change career paths. Though it’s becoming more and more common for people to spend less and less time at each job they hold, you certainly don’t want to give your employer any doubts about your commitment to the role.

The Best Way to Answer: You don’t have to profess that you absolutely see yourself with the same company. Instead, answer in a way that demonstrates your commitment to growing within your field. Employers want to hire employees who are self-motivated and who have an inner drive to better themselves and keep learning. But, keep in mind that an employer may follow up with a question asking about specifics, so if possible have a few key tangible goals you’d like to accomplish.

Sample Answer: “I see myself working within this field, but I hope to have progressed to a higher level of responsibility, possess a greater degree of knowledge, and advance and expand my skill set. I always want to keep learning, keep getting better, and I hope after five years my efforts will carry me closer and closer to becoming an expert at what I do. That being said, I’m also committed to staying happy and fulfilled with my career so that, too, factors into my five-year plans.”

7. What do you think your references will say about you?

The Trap: Employers want to see if you’re insecure about your references and if you’ll volunteer any negative information about your prior experience or your ability to succeed in your role.

The Best Way to Answer: Simply put, don’t fall for the trap, but do be modest. Under no circumstances should you offer up any negative information. Your references wouldn’t have agreed to serve as references if they weren’t willing to speak positively about you.

Sample Answer: “I’ve had a wonderful experience working with all of my references, so I do expect their testimonials to reflect all that we’ve accomplished together at work, along with the positive rapport we share personally.”

8. Which part of the job description sounds most challenging, and why?

The Trap: Are you really as experienced as you say you are? When it comes to a job description, there will likely be aspects that you can ace, and aspects that will cause you some trouble. Employers want to know if your strengths align with their greatest needs.

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The Best Way to Answer: A lie about your skills will come to haunt you later, so be honest. At the same time, use the answer as an opportunity to present yourself as a candidate who is always up for a challenge, and who is sharpening your skills to keep up with that challenge.

Sample Answer: “As a visual designer, the bulk of my experience has been in graphic design, specifically logos, posters, and advertisements. I find dynamic web design more challenging, but challenges like that I live for. I just completed an online course on designing for mobile apps, and I’m currently taking another one in user experience design to ensure my abilities keep up with the latest trends.”

9 Tell me about your dream job.

The Trap: In many cases, passion breeds productivity. Dedication leads to success. Employers want to know just how invested you’ll be in the role, or if you see the job as a stop-gap measure just to keep up some income while you hunt for something better.

Along the same lines, employers want to know if you love the idea of the job, or the job itself. Just because a job title sounds glamorous, doesn’t mean you’ll love the day-to-day work.

How to Answer: Is the job you’re applying for your dream job? If yes, then say so, emphatically. If your dream job is far-flung or far-fetched, it’s probably best not to mention it. You want the employer to understand that you’ll be fully invested in the position and not daydreaming about some other position while you’re at the desk. If the job you’re applying for is somewhere in between, you can tactfully frame your answer to convey that.

Sample Answer: “Advertising is my dream field and the junior copywriting position is an ideal placement for me right now. Of course, I know I have lots of learning to do before I can achieve my dream job – a creative director – and I believe this job will put me on that path.”

10. Everyone has one exaggeration on their job application. What’s yours?

The Trap: Will you fall for your interviewer’s attempt to persuade you into admitting that’s an exaggeration or a little white lie within your application? Hopefully not. And hopefully, your cover letter or resume is free from any mistruths. It’s never worth lying on your application.

How to Answer: Keep your cover letter and resume honest so you can be honest when you answer. (Did you lie on your resume? Here’s what to do.)

Sample Answer: “I’m confident that my cover letter, resume, and portfolio accurately represents my experience and my work. You are welcome to reach out to the references I provided if you’d like them to vouch for my attributes.”

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