Toughest Interview Questions and How to Answer Them

Portrait of mature businessman looking at his secretary while speaking to her   When interviewing for a job, there are some key questions that trip up many interviewees. If you can master some of the more difficult interview questions, you will feel more confident going into the interview. Here are some of the hardest questions interviewees say they have encountered:

What is your greatest weakness?

This question is difficult because it involves a balance between not seeming too self deprecating and not too arrogant. You do not want to choose something that is too obviously not a weakness, such saying you are “too hardworking.” And you do not want to choose something that will actually be a major hindrance to doing your job, such as saying you are “too emotional.” The best is to choose something specific enough that other people will not choose the same one. As an example: “I am detailed-oriented and so sometimes when communicating with others I am overly detailed, which can lead to me not being able to effectively communicate the big picture.” Also include ways that you are working on addressing this weakness, or how it can also be a positive given the proper circumstance.

Are you interviewing with any other companies?

The purpose of this question, from a hiring manager’s point of view, is to determine how likely it will be that this person is able to be hired. It is also so that hiring managers can determine how well you are able to handle a sensitive question that can make you feel awkward. The best is to keep the answer general, and stay positive about the reasons you are interviewing with the current company.

Why did you leave your last position?

Sometimes this question can feel like a probe into the cobwebs of your past life. They key is to not have negative emotions in your answer, even if there are hard feelings from the past. You should be the author of your life and your past story. Even a simple re-framing of a circumstance can make a big difference. Do not say you left because “the company only promotes people who are close to the top boss.” Instead, you can say, “I wanted to work at a company that has a culture that fosters growth at all levels.” This will be a positive answer, especially if the company you are interviewing with is known for career development.

What is your expected salary?

Many people feel pressure to respond to this right away, but if you just respond without proper forethought then you may regret later on. This is because you may sell yourself short of a higher salary without proper research. If it is the first time that you are asked this question, then it is acceptable for you to let the interviewer know that you will research and let them know later. Then, research the company and other people in similar positions, and speak to your career counselor and come back with a proper range.


PLUS Career holds mock interviews with each of our candidates so that they are able to effectively answer even the most difficult interview questions. The questions above were collected from some of the questions our candidates have encountered.