Tough Interview Questions--and How to Answer Them

We’ve all been there. You’ve prepared for the interview, reviewed your resume, and are looking good in your wrinkle-free suit. Then it happens—a question from out of left field (or even one you might have expected, but were dreading). How do you deal?

First and foremost, don’t lose your cool. Interviewing is as much about form as it is about substance—in other words, even if you’re not sure how to answer, it’s important that you act calm, confident, and poised. It’s perfectly acceptable to take a moment, compose yourself, and even admit that the question is a difficult one. Below, I take a stab at some of the most difficult questions an interviewer might throw your way.

“So, tell me about yourself.”

While this might be an intimidating question, it’s actually one of the best opportunities an interviewer can give you because you can answer any way you’d like. Prepare for this question by going over your resume as well as the qualifications and responsibilities listed in the original job posting. Then, give your interviewer a short summary of your background and career path thus far, making sure to focus on those experiences that are relevant to the position. The description should end with why you applied for this role, how it fits into your trajectory and why you are excited about it.

“What is your greatest weakness?”

This question is overdone and verging on cliché, but it still comes up in many interviews. In answering, there are two rules of thumb to follow. First, do not say that you are a perfectionist, that you work too hard, or that you are over-ambitious. These are not weaknesses, and it can come across as arrogant to list them as such.

Instead, name an actual weakness, but follow up by describing what you have done to overcome this trait. For example, if you are not good at delegating, explain that you have addressed this by ensuring that colleagues are adequately trained and prepared to succeed at any assignments you give them. If you have trouble multi-tasking, talk about the organizational system you have implemented to allow you to move seamlessly from task to task.

Of course, there are some weaknesses that are never an appropriate answer to this question. If you frequently miss deadlines or don’t get along well with co-workers, keep it to yourself and work on addressing those problems as soon as possible!

“Have you ever had a conflict with a co-worker? How did you solve it?”

The answer to this question is not, “No.” Conflicts arise in the workplace, and employers want to know that you will be able to resolve them effectively. The best situations to talk about in response to this question deal with work-related (not personal) conflicts. Describe a time where you and a colleague differed on your approach to an assignment. Then, explain the steps you took to come to an agreement. The anecdote should not end with a description of who “won,” but rather how you reached a compromise with your colleague.

This question illustrates why it is so important to prepare for tough interview questions—while you may be able to rattle off a list of colleagues who irk you at a moment’s notice, it is much more difficult to come up with a concrete example of a conflict that ended well. Think back on all the projects you have worked on—a “conflict” doesn’t necessarily have to be heated or argumentative to qualify as an answer to this question.

 “Where do you see yourself in five years?”

This question is especially tough if you are at the beginning of your career, when your path is less clear and you may be unsure where you are headed. What’s most important is to show that you have clear goals, and that the position you are interviewing for makes sense as a part of your trajectory. Make sure that the goals you state are not only compatible with, but directly related to, the role. Most interviewers are proud of their companies and are not interested in hiring someone who sees a job as merely a stepping stone to where they really want to be.

At the same time, hiring managers understand that no one aims to stay in a junior role forever. If you are interviewing for an entry-level position, talk about your passion for the industry and your interest in advancing in your field. If the company employs more senior people in the same area, you can talk about eventually gaining more responsibility and contributing more substantively to the organization. The one exception is that at a very small company, it can come across as aggressive to talk about moving up in the ranks—in this situation, focus on growing within the industry in general.

Working the Conversation

Above all, remember that as the interviewee, you have more power than you might think to control the substance and direction of the conversation. If there’s a specific experience or past role you want to talk about, don’t wait for a specific question about it—work it into a response to another question. Use concrete examples whenever possible. With enough preparation, you might even start to look forward to getting the toughest questions!