Savvy hiring managers can glean a ton of information about you by asking just a few, well-chosen questions.
But while they may seem simple, some are actually designed to get you to reveal information you may have been trying to conceal. In other words: they’re trick questions.
“To uncover areas that may reflect inconsistencies, hiring managers sometimes ask these tricky questions,” said Tina Nicolai, executive career coach and founder of Resume Writers’ Ink.
But they’re not just about exposing your flaws, said Lynn Taylor, a national workplace expert and the author of “Tame Your Terrible Office Tyrant.”
“Their real agenda is for your answers to ultimately paint a picture that you are the perfect fit for the job — not just on paper, but from an overall trust standpoint,” Taylor said.
Here are 21 common examples of tricky job interview questions, complete with advice on how to ace each one:
Can you tell me about yourself?
Why do they ask this? They ask to determine how the candidates see themselves as it pertains to the position and how confidently they can communicate their skills. “The employer wants to hear that the candidate did their homework,” Nicolai said. “If this opening answer is weak, it can send the remainder of the interview into a tailspin or cut the interview short.”
What makes it tricky? It can tempt you to talk about your personal life — which you shouldn’t! “Most candidates are not versed in seeing this as a trick question, so they may answer by speaking from a personal perspective: ‘I have three kids, I’m married, etc,'” Nicolai said.
What response are they looking for? A focused answer conveying your value to the organization and department. “The employer wants to hear about your achievements, broken down into two or three succinct bullet answers that will set the tone of the interview,” Nicolai said.
Try this, from Nicolai: “I am known for turning around poor performance teams as a result of my innate skills in analyzing problems and seeing solutions very quickly.”
This statement tells the interviewer that the candidate has analytical skills, problem-solving ability, and leadership ability that enables them to turn around business performance.
How would you describe yourself in one word?
Why do they ask this? Through that one word, Taylor said employers will be able to assess your personality type, how confident you are in your self-perception, and whether your work style is a good fit for the job.
What makes it tricky? This question can be a challenge, particularly early on in the interview, because you don’t really know what personality type the manager is seeking. “There is a fine line between sounding self-congratulatory versus confident, and humble versus timid,” Taylor said. “And people are multifaceted, so putting a short label on oneself can seem nearly impossible.”
What response are they looking for? Proceed cautiously. “If you know you’re reliable and dedicated, but love the fact that your friends praise your clever humor, stick with the conservative route,” Taylor said.
If you’re applying for an accounting job, the one-word descriptor should not be “creative,” and if it’s an art director position, you don’t want it to be, “punctual,” for example.
“Most employers today are seeking team players that are levelheaded under pressure, upbeat, honest, reliable, and dedicated,” Taylor said.
How does this position compare to others you are applying for?
Why do they ask this? They’re basically asking: “Are you applying for other jobs?” And they want to see how you speak about other companies or positions that hold your interest — and how honest you are.
What makes it tricky? If you respond, “This is the only job I’m applying for,” your interviewer will worry. Very few job applicants apply to only one job, so they may assume you’re being dishonest. But if you’re too effusive about your other prospects, however, the hiring manager may see you as unattainable and pass. “Speaking negatively about other jobs or employers isn’t good either,” Nicolai added.
What response are they looking for? Go with this response, Nicolai said: “There are several organizations with whom I am interviewing, however, I’ve not yet decided the best fit for my next career move.”
“This is positive and protects the competitors,” Nicolai said. “No reason to pit companies or to brag.”
Can you name three of your strengths and weaknesses?
Why do they ask this? The interviewer is looking for red flags and deal-breakers, such as an inability to work well with coworkers or an inability to meet deadlines.
“Each job has its unique requirements, so your answers should showcase applicable strengths, and your weaknesses should have a silver lining,” Taylor said. “At the very least, you should indicate that negative attributes have diminished because of positive actions you’ve taken.”
What makes it tricky? You can sabotage yourself addressing either. Exposing your weaknesses can hurt you if you don’t explain how you’re taking steps to address them, Taylor said. “Your strengths may not align with the skill set or work style required for the job. It’s best to prepare for this question in advance, or risk landing in a minefield.”
What response are they looking for? First of all, do not say your weakness is that you “work too hard.” Interviewers are “looking for your ability to self-assess with maturity and confidence,” Taylor said.
Furthermore, hiring managers want to know that your strengths will be a direct asset to the new position, and that none of your weaknesses would hurt your ability to perform.
Why do you want to work here?
Why do they ask this? Interviewers ask this because they want to know what drives you the most, how well you’ve researched them as an organization, and how much you want the job.
What makes it tricky? “Clearly you want to work for the firm for several reasons,” Taylor said. “But just how you prioritize them reveals a lot about what is important to you.”
You may be thinking to yourself, “I’m not getting paid what I’m worth,” or, “I have a terrible boss,” or, “All things being equal, this commute is incredibly short” — none of which endears you to the hiring manager.
What response are they looking for? Hiring managers want to see that you’ve taken the time to research the company and understand the industry.
Why do you want to leave your current job?
Why do they ask this? “Your prospective boss is looking for patterns or anything negative, especially if your positions are many and short-term,” Taylor said. The interviewer may try to determine whether you have had issues working with others leading to termination, if you get bored quickly in a job, or other red flags.
What makes it tricky? If not answered diplomatically, your answer could raise further questions and doubts or sink your chances entirely.
What response are they looking for? They hope you are seeking a more challenging position that is a better fit for your skill set or that there’s something specific about their company that you’re drawn to, Taylor said.
What are you most proud of in your career?
Why do they ask this? Interviewers want to understand what you’re passionate about, what you feel you excel at, and whether you take pride in your work.
“How you describe your favorite project, for example, is almost as important as the project itself,” Taylor said. “It’s assumed that if you can speak with conviction and pride about your past work, you can do the same during important presentations at the new employer.”
What makes it tricky? Managers may assume that this type of work is what you really want to do most or focus on in the future. It can make you sound one-dimensional if you don’t put it in the context of a larger range of skills and interests.
What response are they looking for? Hiring managers want to see your ability to articulate well and foster enthusiasm in others, as well as your positive energy.
Have you ever considered being an entrepreneur?
Why do they ask this? The interviewer is testing to see if you still have the hidden desire to run your own company, thus abandoning ship, Taylor said. “No firm wants to sense this, as they will begin to ponder whether their valuable training time and money could vanish.”
What makes it tricky? Most everyone has considered being an entrepreneur at some point in their lives, but to varying degrees. This question is tricky because you can unwittingly be lured into talking about your one-time desire to be your own boss with too much perceived enthusiasm. An employer may fear that you still hope to eventually go out on your own and consider you a flight risk.
On the other hand, saying “no” outright might indicate you’re not a self-starter.
What response are they looking for? It’s OK to tell a prospective manager that you once considered entrepreneurship or have worked as an independent contractor, Taylor said. It can easily be turned into a positive by saying that you’ve already experienced it or thought about it, and it’s not for you. And that might be more convincing than saying, “No, I’ve never considered that.”
This is an opportunity to discuss why working in a corporate environment as part of a team is most fulfilling to you. You may also enjoy the specialized work in your field more than the operational, financial, or administrative aspects of entrepreneurship.
Have you ever stolen a pen from work?
Why do they ask this? James Reed, author of “Why You?: 101 Interview Questions You’ll Never Fear Again,” wrote in his book that hiring managers who ask this are not worried about their inventory — they’re just trying to get a better sense of your level of integrity.
What makes it tricky? We’ve all taken a pen or two, so if you say that you haven’t, then they might think you’re a liar. But if you say that you do it all the time and act like it’s no big deal, then that could be problematic, too.
Reed, who is also the chairman of Reed, a top job site in the UK and Europe, wrote in his book that saying something like “I have once or twice taken a pen from the office in an emergency but I have always returned it the next day or the day after” is a terrible response. Why? The interviewer knows that pen is still on your desk at home and might challenge you.
What response are they looking for? In his book, Reed wrote that going with something more realistic, like: “Well, I’d be lying to say I haven’t ever absentmindedly slipped a ballpoint into my jacket pocket, but it usually ends up back on my desk the following day, unless I leave it at home. I haven’t got a spare room full of paperclips and staplers, though, if that’s what you mean.”
What kind of boss and coworkers have you had the most and least success with, and why?
Why do they ask this? Interviewers are trying to ascertain if you generally have conflicts with people and/or personality types, Taylor said.
What makes it tricky? You run the risk of appearing difficult by admitting to unsuccessful interactions with others, unless you keep emotions out of it. You may also inadvertently describe some of the attributes of your prospective boss. If you said, “I had a boss who held so many meetings that it was hard to get my work done,” and your interviewer turns beet red — you might have hit a nerve.
What response are they looking for? “They want to hear more good than bad news,” Taylor said. “It’s always best to start out with the positive and downplay the negatives.”
You don’t want to be evasive, but this is not the time to outline all your personality shortcomings either. This is an opportunity to speak generally about traits that you admire in others yet appear flexible enough to work with a variety of personality types.
Taylor recommended you say: “I think I work well with a wide gamut of personalities. Some of my most successful relationships have been where both people communicated very well and set mutual expectations up front.”
If you could work for any company, where would you work?
Why do they ask this? Hiring managers want to ascertain how serious you are about working for them in particular, versus the competition, as well as your level of loyalty, Taylor said.
What makes it tricky? You might get caught up in the casual flow of the discussion and inadvertently leak out some well-respected firms, but this is counterproductive and only instills some doubt about your objectives.
What response are they looking for? “Your interviewer wants to know that you’re interviewing at your first company of choice,” Taylor said.
Try this response: “Actually, I’ve been heavily researching target firms, and (your company] seems like the ideal fit for my credentials. It’s exciting to me that (your company] is doing XYZ in the industry, for example, and I’d like to contribute my part.”
How do you define success?
Why do they ask this? Interviewers want insight into your priorities: are you motivated by big paychecks? Being challenged? Learning new skills? “Or,” Taylor added, “do you take a more personal, individualistic approach to success?”
What makes it tricky? This one is a minefield, since “success” is highly subjective, and even a perfectly reasonable response can be easily misinterpreted, Taylor said. “There’s a fine line between sounding ambitious and appearing as if you’re eyeing the top spot in the office — because you ‘really want to advance and make a difference.'”
What response are they looking for? When questions are broad and leave a lot of room for “a virtual inquisition,” Taylor advises keeping your answers relatively unobjectionable. “Try to define success in a way that relates to the prospective employer, based on what you know from the job description and conversation,” she said. A good response? “Applying my brand expertise to the strategic marketing goals you’ve established for XYZ company, building on your existing success.”
What career regrets do you have?
Why do they ask this? Reed wrote that the interviewer is really asking, “Is there something bad about you that I cannot see, and if there is, can I get you to admit it? Do you carry psychological baggage that you don’t need? How readily do you forgive yourself — and others?”
What makes it tricky? “Regret is a loaded word: don’t point it your way,” Reed wrote.
What response are they looking for? Reed suggested giving the interviewer “a little bit of grit,” but says you should try to avoid using the word “regret.”
Instead, “focus on something positive and say you wished you’d done more of it. Then stop talking.”
Here’s an edited version of the sample answer Reed offered in his book:
“All told, I don’t have too many complaints about the way things have gone. If I could change one thing, I’d have moved into the cell phone insurance business sooner than I did. I turned out to be good at that, and I enjoy it too. … If I’d moved into it sooner then maybe I’d have been sitting here a couple of years earlier — but who knows? Missing out on that taught me to take the odd risk in life, and I’m thankful for that.”
Why were you laid off?
Why do they ask this? “Employers want to know how you hold up under pressure and less fortunate circumstances such as job loss,” Nicolai says. “They want to hear that you are positive and ready to get back to work with a great attitude. They also want to hear a level of confidence — not defeat or anger.”
What makes it tricky? For starters, you may be bitter or angry about the layoff, and this question may prompt you to bad-mouth your former employer, which you never want to do in a job interview.
“Stay away from finger pointing, desperation, or portraying a victim,” she adds.
What response are they looking for? “Provide a level-headed answer that is focused on a business decision by the company to conduct the layoff,” Nicolai says. “Be sure to not cast blame or any discontent. Stay on track with the facts as you know them.”
What would you do if you won $5 million tomorrow?
Why do they ask this? They want to know whether you would still work if you did not need the money. Your response to this question tells the employer about your motivation and work ethic. The interviewer may also want to know what you would spend the money on or whether you would invest it. This illustrates how responsible you are with your money and how mature you are as a person.
What makes it tricky? Questions that are out of left field can ambush you, causing you to lose composure. “They have nothing to do with the job at hand, and you may wonder if there is any significance to them,” Taylor said. “Whether there is or not, the fact remains that you can easily lose your cool if you don’t pause and gather your thoughts before you respond to a question like this.”
What response are they looking for? They want to hear that you would continue working because you’re passionate about what you do — and they want to know you would make smart financial decisions. If you would do something irresponsible with your own money, they’ll worry you’ll be careless with theirs.
Have you ever been asked to compromise your integrity by your supervisor or colleague?
Why do they ask this? Your prospective boss is evaluating your moral compass by asking how you handled a delicate situation that put your integrity to the test, Taylor said. “They may also dig too deeply to test your level of discretion.” Essentially they want to know: Did you use diplomacy? Did you publicly blow the whistle? Did a backlash ensue? What was your thought process?
What makes it tricky? Interviewers want to know how you manage sensitive matters and are also wary of those who bad-mouth former employers, no matter how serious the misdeed. “They will be concerned if you share too much proprietary information with the interviewer,” Taylor said. “So it is tricky because you must carefully choose your words, using the utmost diplomacy.”
What response are they looking for? It’s wise to be clear, concise, and professional in your answer, without revealing any internal practices of prior employers. “You have nothing to gain by divulging private corporation information.”
Something like this might work: “There was one time where a fellow worker asked me to get involved in a project that seemed unethical, but the problem resolved itself. I try to be as honest as possible early on if a project creates concern for me about the company, as I’m very dedicated to its success.”
Can you give us a reason someone may not like working with you?
Why do they ask this? Prospective bosses want to know if there are any glaring personality issues, and what better way than to go directly to the source? “They figure that the worst that can happen is you will lie, and they may feel they’re still adept at detecting mistruths,” Taylor said. “The negative tone of the question is bound to test the mettle of even the most seasoned business professionals.”
What makes it tricky? You can easily shoot yourself in the foot with this question. If you flip and say, “I can’t think of a reason anyone wouldn’t like working with me,” you’re subtly insulting the interviewer by trivializing the question.
So you have to frame the question in a way that gets at the intent without being too hard on yourself. “Hiring managers are not seeking job candidates who have self-pity,” she said.
What response are they looking for? You don’t want to say, “Well I’m not always the easiest person to be around, particularly when under deadlines. I sometimes lose my temper too easily.” You might as well pack up and look for the nearest exit.
Taylor suggested this response: “Generally I’ve been fortunate to have great relationships at all my jobs. The only times I have been disliked — and it was temporary — was when I needed to challenge my staff to perform better. Sometimes I feel we must make unpopular decisions that are for the larger good of the company.”
Why have you been out of work for so long?
Why do they ask this? “Interviewers are skeptical by design,” Taylor said. “Sometimes you’re guilty until proven innocent — until all the perceived skeletons in the closet have been removed.” This is a daunting question in particular because it can seem offensive.
The implication is that you might not be motivated enough to secure a job; you are being distracted by other pursuits; your skills set may not be up to date; there is an issue with your past employers, or a host of other concerns.
What makes it tricky? The way it’s worded is naturally designed to test your resilience. The key is not to take the bait and just answer the intent of the question in a calm, factual manner.
What response are they looking for? The hiring manager wants to be assured that you possess initiative even when unemployed, as this drive and tenacity will translate well in a corporate setting.
Sample responses: “I have been interviewing steadily, but want to find the ideal fit before I jump in and give my typical 110%,” or, “I’m active in my job search, and I keep my skills current through [courses, volunteering, social media, business networking groups].”
“If you took off time to take care of a personal matter, you can certainly state that without giving a lot of detail,” Taylor said.
Make sure you’re accountable. Don’t blame the unemployment rate, your market, industry, or anything else. This is about how active and excited you are to be making a contribution to the employer.
Tell me about a time you disagreed with a company policy.
Why do they ask this? To determine your decision-making ability, ease of working with others, and most importantly, whether the candidate will speak up after identifying an area in need of improvement.
What makes it tricky? “To say, ‘I’ve never disagreed with a company policy’ is tough to believe from even the most amenable employee,” Nicolai said. “This also sends a message that you may just accept anything that you are told to do without thinking through all possible outcomes.”
Companies want leaders and employees to follow the rules, but they also want people who are going to review potential outdated policies and have the courage to push back and propose changes to maintain a current, competitive edge and productive workplace.
What response are they looking for? Talk about a time when you opposed a policy for a logical and business reason.
“Focus on how your idea to rework the policy was beneficial to the company as a whole. Speak up on the research that you conducted, the facts that you presented, and the outcome of your attempts to have the policy rewritten,” Taylor said.
How did you make time for this interview? Where does your boss think you are right now?
Why do they ask this? Hiring managers want to find out if your priorities are in the right place: current job first, interviews second.
“They know that the habits you follow now speak to your integrity and how you will treat your job at their company should you undertake a future job search,” Taylor said. “They also want to know how you handle awkward situations where you cannot be truthful to your boss. Ideally, your interview is during a break that is your time, which is important to point out.”
What makes it tricky? The implication is that you’re breaking a company rule. For most employed job seekers, it’s uncomfortable to lie about their whereabouts. So they’re vague and treat it like any other personal matter they handle on their time.
What response are they looking for? It’s wise to explain that you always put your job first, and schedule interviews before or after work, at lunchtime, during weekends if appropriate, and during personal time off.
Try something like: “My boss understands that I have certain break periods and personal time — he doesn’t ask for details. He’s most interested in my results.”
What’s a difficult situation that you turned around?
What do they ask this? This gives hiring managers a lot of information in one fell swoop, Taylor said. They want to know “not only know how you handle stressful situations, but also how you think through problems, how you define ‘difficult,’ and what courses of action you take when faced with any form of adversity.”
What makes it tricky? It’s easy to interpret this as an invitation to brag about the success of your turnaround. Don’t fall for it. “The emphasis is really on how you generally problem-solve under pressure,” Taylor said. “Do you illustrate any signs of stress as you describe the event? Were you creative, resourceful and prompt in its resolution? Did you follow a logical path in doing so?” Choose your examples extremely carefully, since they’ll give employers a glimpse at what you consider to be “difficult.”
What response are they looking for? Interviewers want to see that you’re a good problem solver, Taylor said. “They place a premium on those who can think clearly, remain professional when under the gun — and those who can recover quickly from setbacks.”
To ace the question, be sure you go into the meeting by preparing with a few examples of times you successfully overcame significant professional challenges.
This article first appeared on Business Insider.