Five of the Most Difficult Job Interview Questions, and How To Answer Each One

By Rafael Magaña

The average job interview is designed to feature at least a few tough moments. Generally, the hardest part is answering the challenging questions that interviewers like to spring on prospective candidates. Knowing how to handle these tricky questions is a valuable skill. Here are five of the most common difficult job interview questions, and how to deal with each one.

1. Where do you plan on being in five (or three, or seven) years?

There are a few reasons why this question can be a landmine. If an applicant aims too high or says they plan to be at a different company, it will sound as if they aren’t interested in the job they are actually applying for. But, on the other hand, saying that being in the exact same position would be just fine shows a lack of ambition. The best strategy is to emphasize a healthy interest in career advancement, without getting too specific. Show your interest in personal development and share how you enjoy taking training that helps you improve planning budgets, programs, managing large teams, risk management, and social media communication to name a few.

Remember you are interviewing them as well. As I have gotten older and wiser I have found that no organization is without problems. I recently reversed this question back to a panel of distinguished interviewers. Guess what happened? You could hear a pin drop. The answers I received were all over the place. Almost none of my potential coworkers saw themselves within the organization in two years. That gave me the answer I needed hear and move on and politely decline the package offer.

2. What is your biggest weakness?

This question is difficult because it requires the prospective employee, who wants to present themselves in the best possible light, to be critical instead. While a response such as “I work too hard” might seem clever, interviewers will correctly view answers like this as disingenuous. A better approach is to acknowledge a genuine weakness but to explain what is being doing to improve the shortcoming. This will shift the emphasis from the weakness itself to the applicant’s adaptability and capacity for growth.

3. What was your greatest failure?

This is another question that demands the interviewee reveal negative information. A similar approach, focusing on the positive side of the failure, can be used here. After all, since setbacks and mistakes are ultimately inevitable, what’s really important is how someone responds after they fail. So, after briefly describing the failure, the applicant should devote the rest of their answer to explaining what they did afterwards to fix the mess they created. This reframes the failure as something more positive and turns a difficult question into a chance to show off valuable problem-solving skills.

4. What did you not like about your previous job?

This question is troublesome because it invites the prospective employee to reveal privy information about their former company. Tempting as it may be to vent frustrations about bosses, colleagues, or company policies, doing so is a bad idea. A manager will not want to hire an applicant who might be a malcontent or who might have a bad attitude. An applicant should instead opt for anodyne, politically correct answers that showcase a desire to become a better employee. For example, replies like “I needed more responsibility” or “I didn’t feel as if I was reaching my full potential” are great.

5. Why did you leave your previous position?

If an interviewee left their last job of their own accord, this question may not be especially difficult. However, for those who were let go, this question can be extremely tough. The only solution is honesty. Deception might be tempting, but since managers will usually look to verify whatever story the applicant tells, the plain truth is the only real option. The applicant should simply explain the circumstances surrounding their dismissal candidly. If they were let go because of company layoffs, the event probably won’t be perceived negatively anyway. The job candidate can also dispel doubts by emphasizing how valuable of an employee they were before their dismissal.

Job interviews can be challenging experiences, especially when particularly tricky questions are asked, such as those five described above. But, it actually makes sense to view these difficult questions as valuable opportunities, rather than something to be dreaded. That’s because, since most job applicants will struggle with the tough questions, answering them skillfully can provide an important advantage over other candidates.


Copyright July 28, 2017 by Rafael Magaña. Contact for usage license.

About the Author: Rafael Magaña helps organizations grow. Helps leaders accelerate strategy implementation in their organizations. Actively works with teams to support cause awareness initiatives. He is the Major Gift Director at the Pasadena Humane Society. He is a board member of three nonprofits. He resides in California. UCLA Alumni.

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