top of page

The 5 Most Difficult Interview Questions and How to Answer Them

Updated: May 5, 2023

A small white office chair is centered in the middle of the image with the entirety of the background shaded in black.

Interviewing for a new job is both exciting and intimidating. From the moment you meet with a potential employer, they are evaluating your candidacy for the advertised position (see our interviewing basics article for tips and tricks to nail the interview). A key element of any interview is the interviewer’s analysis of how you answer the questions. While there will always be a few more challenging, possibly position-specific questions, preparing for some of the most difficult interview questions can reduce your stress and set you up for success.

1. “Tell me about yourself.”

When an interviewer asks this question, they are not looking for personal details like where you were born or your hobbies. Instead, they are trying to get an idea of your potential fit within the company culture as well as how well you will meet the requirements of the position. It’s critical to connect your skills to the position you are interviewing for. Review and make sure you understand the demands of the position and then think about the skills you’ve developed and the contributions you’ve made in previous jobs. Consider how these skills and achievements can be applied to the job you are seeking.

2. “Why should we hire you instead of the next candidate?”

This is of course a trick question in that there is no way you could accurately know another candidate’s qualifications for the position. Always make sure to respond respectfully towards the other candidate and the company, including a short introduction to your answer such as “I’m sure all of the candidates for this position are well-qualified” before explaining how select highlights of your job history align with the company’s needs. This is your chance to give your “elevator pitch” as well as a perfect opportunity to drive home the notion that you are the perfect match for the advertised position.

3. Where do you see yourself in a year/five years?”

Interviewers that ask about your future plans are often simply checking to see if you think about the future and whether you consider their company part of the plan. Employers want to know if the position you are vying for is part of a greater career plan or just an inconsequential step along the way. They also may be thinking of your ability to commit to the company and by extension its success – if you reveal that you are planning to move halfway across the country in the next 18 months, the likelihood is that you will be leaving the position relatively quickly.

4. “What role do you play on a team?”

This is another question that in its simplicity provides a wealth of information regarding your flexibility, willingness, and ability to function in variety of different capacities as a team member and potentially a leader. It is important to back up your claims and responses with specific examples of leadership, collaboration, contributions, and other examples of the impact and role(s) you can play. There are also situations in which it may be best to focus on one facet of teamwork – for example, if you are interviewing for a management role, it may benefit you to focus primarily on your leadership and motivational skills in addition to your ability to delegate and be accountable for your decisions as a leader.

5. “Why are you leaving your current position?”

People leave jobs for a variety of reasons all of which are highly subjective and usually personal. The key is positivity. No one wants to inherit someone else’s problems. Never criticize your previous employer or complain about the position or positions you filled. Instead, focus on your achievements and beneficial reasons for leaving, including those that support your professional goals. For example, you could explain that you are considering leaving your current position to seek new challenges, or you are looking to grow beyond the boundaries of that role.

While many facets of the job search process are changing, such as the predominance of video interviewing and remote work (see our video interviewing and work-from-home articles), many of the basic interviewing techniques remain the same. There are several common and sometimes tricky tactics used by interviewers to discover your true character and what is driving your decisions. With forethought and careful preparation, you can use these questions to your advantage and really “wow” a potential employer to land the job.


bottom of page