12 Sneaky Interview Questions That Are Designed To Trick You

We want to start by offering the following reassurance: nine times out of ten, employers aren’t formulating interview questions with the express purpose of tripping you up. They’re asking for information that can legitimately help them come to a hiring decision, and they have nothing to gain from blindsiding you with a “Gotcha!” just for the heck of it. 

That said, employers can gather useful intel by including a few inquiries that require quick thinking and on-the-spot personal analysis. Business Insider compiled a list of common “tricky” questions, and I’ve selected a few highlights (and added some questions of my own) to give you a pre-interview head start.

1. “What can you tell me about yourself?”

This one couldn’t seem more straightforward, but it’s important to recognize what the employer actually hopes to discern when asking this question. Don’t focus on your personal life, tailor your responses to highlight specific past accomplishments and be sure to keep your professional strengths at the forefront.

2. “How would you describe yourself in one word?”

A variation on the first question, this one seeks to get down to the nitty-gritty of your personality and how it will fit into the company culture. 

“They want to know about your personality type, how confident you are in your self perception, and whether your work style is a good fit for the job,” career expert Lynn Taylor told Business Insider. Answer with a positive attribute that you think will make you successful in this particular role, and you’ll be in good shape. 

3. “How does this position compare to others you are applying for?”

This question provides an example of the power of an honest-but-measured interview response. You don’t want to say “I’m not applying anywhere else,” as that will read as disingenuous and suspicious. At the same time, talking up the amazing features of the other jobs you’re applying for may cause this company to dismiss you as unattainable. Business Insider suggests a balanced approach, like "there are several organizations with whom I am interviewing, however, I've not yet decided the best fit for my next career move."

4. “Why do you want to leave your current job?”

When discussing your current job or past positions in an interview, try to avoid dwelling on the negative. Sure, your boss might be a space cadet and your company culture may be toxic... but those comments won’t endear you to this new company. Instead, focus on the desirable attributes offered by this new position. “"Know that hiring managers don't mind hearing that you're particularly excited about the growth opportunity at their company," Taylor explained to BI.

5.“What could your current company do to keep you?”

This slight spin on the “Why do you want to leave?” question feels particularly tricky, but the same principles should apply for your response. Emphasize what you’re looking for from your next position rather than what’s lacking in your current one, and you’ll come across as driven and goal-oriented.

6. “Can you name three of your strengths and weaknesses?”

Perhaps the most classic interview question of them all, “What are your strengths and weaknesses?” is an exercise in self-reflection. While Taylor advised BI to “ultimately turn [your weaknesses] into strengths,” I'm going to respectfully disagree. The old “my weakness is actually my strength!” trick is a tired one, and hiring managers have seen it countless times before. The problem? It doesn’t address their actual point of interest (your ability to evaluate your own strong suits and areas that need improvement). A better bet involves being honest about your weaknesses, but actively mentioning the steps you’re taking to grow and evolve.

7. "Why do you want to work here?”

This question offers you the opportunity to show this company how much you’ve researched them and why your skills and experience make you a strong fit for their needs and culture. Business Insider breaks down the key elements of this question: “They want to know that you actually want this job (and not just any job); that you have a can-do attitude; that you are high energy; that you can make a significant contribution; that you understand their mission and goals; and that you want to be part of that mission.”

8. "What are you most proud of in your career?”

The hiring manager already has a clue regarding your points of career-related pride: your resume, which should be a well-curated marketing document highlighting your greatest professional achievements. But the way you talk about these accomplishments reveals a great deal about your passions and your dedication. Stay clear and concise, but don’t shy away from genuine expressions of confidence. You’ve earned them!

9. “What kind of bosses and coworkers have you had the most and least success with, and why?”

Another culture-centric query, this question is “trying to ascertain if you generally have conflicts with people and/or personality types,” BI claims. BI goes on to recommend keeping your cool and orienting your answer in a positive direction. 

10. “How do you handle stress?”

Interviewers, particularly those who in professions with considerable amounts of high-value and time-sensitive work, want to know that you can withstand a reasonable quantity of workplace pressure with strategy and grace. Rather than regaling your interview panel with an account of your extracurricular yoga and meditation practices, consider narrowing your focus to the tactics you use to deal with stress while in the office.

11. “How have you handled conflicting priorities in the past?”

When hiring, companies actively seek out skilled multitaskers due to their promise of productivity. But if you’re faced with two important tasks and must choose which to prioritize over the other, can you smoothly synthesize the information you have about these assignments and come to a deliberate and well-conceived decision? That’s the “trick” behind this interview question, so an answer that addresses this concern will likely yield a positive response.

12. “How did you spend this gap in your employment?”

There are plenty of extremely valid reasons to have a sizable employment gap on your resume. However, it’s important to realize that interviewers will expect you to have an explanation ready. There’s no need to delve into highly-personal details, but a clear and simple response like “I took some time off to handle a health-related matter that’s since been resolved” will provide the interviewers with useful context.