How to Answer the 3 Trickiest Job Interview Questions

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Once you have decided to launch a job search, the job interview is likely the most critical part of the process—potentially leading to a life-changing position. But when tricky or difficult questions are hurled at you, it can feel like swimming in shark-infested waters. Take heart: You can be prepared for the worst and remain optimistic throughout your search.

There are many interview curveballs that can be thrown at you. But there are also techniques that can give you peace of mind for any tough question. Here are some overall tips to consider when you’re in the hot seat:

• Practice makes perfect. As with all tricky job interview questions, it’s a good idea to prepare your answers in written form and rehearse them. Practice your answers in front of a mirror and develop muscle memory. Of course, you want to avoid sounding rote or like an AI version of yourself, but in a job interview situation, nerves can take over, and you may forget your main points without enough advanced practice.
• Use “bridging” to gain control. During the interview, if you’re given some extra time and you want to amplify your strengths, you can always segue into a broader, positive topic related to the subject. Sometimes, this is called “bridging,” especially into more upbeat territory. An example: “So yes, it was challenging, but my strategic planning paid off. I have learned over the years that the level of preparation for a project can make or break it. Another example of this was when…”
• Prepare three key talking points. It’s always good to have three major points in your back pocket. These should be strong arguments as to why your skills are a good match for the job. When there’s a lull in the conversation, you can always come back to them. The interview is a sales opportunity, after all, but you must come across as genuine.

And now for the three toughest questions, why they’re tricky, and some responses to consider:

1. "What is your biggest weakness?"

Hiring managers may throw this at you to see if you inadvertently divulge a negative characteristic. Typically, interviewers are most concerned with interpersonal issues—as strong emotional intelligence is highly sought after. While no one is perfect, this is not the time to go into a self-sabotage mode.

You certainly want to avoid the classic, hackneyed response, “I’m too much of a perfectionist.” And remember: Whatever you say may go under the microscope later if you’re hired.

There are convincing ways to address weaknesses that could also be viewed as strengths, especially as they relate to the job at hand. For example, for a sales or marketing-oriented position, saying that you can be overly driven at times could be viewed as a positive. If you say you can become very analytical at times, that may be seen as a plus if you’re an accountant.

Ideally, it’s helpful to comment after presenting these “negative” traits. For example, if you claim to be overly driven, you could add that you’ve channeled that by establishing regular, achievable goals in recent years.

After addressing the negative trait issue, you can also bridge to positive, general work styles, such as being dedicated, thorough, or team-oriented. Just be sure to have examples ready for each of the general characteristics you enumerate.

2. "How would your former manager and coworkers describe you?"

It’s always a good idea to discuss this topic with your references in advance. You certainly want your response to align with their comments.

Here, you can address your work style and personality. If you are truly a great team player or possess strong leadership skills, it’s OK to say that, especially if the job requires it. If your coworkers would say you work well independently, and you feel that quality is applicable to the job, be ready to expound on it.

With extra time to address this question, you can explain how these specific traits specifically match up with the position.

3. "How would you describe your last boss?"

Many people leave their managers, not their jobs (so to speak), so this question can be a minefield. One of the biggest concerns for any interviewer is whether a job candidate will be difficult to manage.

Consider describing the positive attributes of your former boss. Granted, that can be hard to do, particularly if you’re leaving a frustrating situation. Think back to earlier times and the qualities they demonstrated when things were better. Perhaps your manager had great knowledge of the industry, was a natural problem-solver, or was a helpful mentor in some respects. It’s always safe to explain that you learned a great deal from your boss and were grateful for the opportunity.

Whatever your response, keep in mind that as you describe your boss, the interviewer is contemplating what you would say about them if you left the new job. So, keep it positive—as that reflects better on you.

You have control, too.

No matter how tricky the interview question is, you can answer a question any way you wish, assuming you stay on topic. It’s best to use that power and the control you do have most effectively—by rehearsing the best answers in advance. Many interviewers want to see how you perform under pressure, but they’re not out to trip you up (although some will try).

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And remember that you are also evaluating them. Make sure you have your own questions ready that demonstrate solid knowledge of the company and industry. Keep your cool, as your dream job could be waiting in the wings, despite those zingers you receive during your interviews.

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