17 interview questions that are designed to trick you

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 — that’s the point — 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,” says Tina Nicolai, executive career coach and founder of Resume Writers’ Ink.

But they’re not just about exposing your flaws, says Lynn Taylor, a national workplace expert and the author of “Tame Your Terrible Office Tyrant: How to Manage Childish Boss Behaviour and Thrive in Your Job.” These types of questions can help hiring managers break through the “traditional interview noise and clutter,” and get to the “raw you.”

Here are 17 common examples, complete with advice on how to ace each one.

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?' 'The hiring manager is first trying to figure out how active you are in your job search,' Nicolai says. Then, once you open up, they want to see how to speak about other companies or positions you're interested in -- and how honest you are.

What makes it tricky? If you say, 'This is the only job I'm applying for,' that will send up a red flag. Very few job applicants only apply to the one single job -- so they may assume you're being dishonest. However, if you openly speak about other positions you're pursuing, and you speak favourably about them, the hiring manager may worry that you'll end up taking another job elsewhere, and they won't want to waste their time. 'Speaking negatively about other jobs or employers isn't good either,' she says.

What response are they looking for? It is appropriate to say, 'There are several organisations 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,' says Nicolai. 'No reason to pit companies or to brag.'

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, and how much you want the job.

What makes it tricky? 'Clearly you want to work for the firm for several reasons,' Taylor says. 'But just how you prioritise 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. 'You're also being tested on your level of interest for the job,' she says.

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.

They also 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.

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 explains. They may try to determine if you currently have or had issues working with others leading to termination, if you get bored quickly in a job, or other red flags.

What makes it tricky? No one likes talking about a job they dislike and why. If not answered diplomatically, your answer could raise further questions and doubts, or sink your chances entirely.

What response are they looking for? They are hoping that you're seeking a more challenging position that is a better fit for your current skill set. 'Know that hiring managers don't mind hearing that you're particularly excited about the growth opportunity at their company.'

What are you most proud of in your career?

Why do they ask this? Interviewers ask this because they 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 favourite project, for example, is almost as important as the project itself,' Taylor says. '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, foster enthusiasm in others, and your positive energy. 'But one note of caution: In all your zeal to share your successes, remain concise,' Taylor suggests. 'You want to showcase your ability to present well once on the job.'

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. 'Secondarily, they want to know how you can work at your best,' says Taylor.

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 say, '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 explains. '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. Here you have an opportunity to speak generally about traits that you admire in others, yet appear flexible enough to work with a variety of personality types. For example: '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 upfront.'

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 says. 'It also helps them weed out candidates who may veer from the core career. You may have heard that Google is a great place to work, but that off-road strategy would spell doom, as you're being given the opportunity to theoretically work at your 'dream job.' The interviewer isn't making conversation here, so stay focused on the job at hand.'

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 are they seeking? 'Your interviewer wants to know that you're interviewing at your first company of choice.' A response to this might be, '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.'

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 that to go direct 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 explains. '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're 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 self-effacing. 'Hiring managers are not seeking job candidates who have self-pity,' she says.

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. 'Conversely, you can lead with the positive and go from there: '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,'' Taylor suggests.

What's a difficult situation that you turned around? Describe it to us.

What do they ask this? This gives hiring managers a lot of information in one fell swoop, explains Taylor. 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 explains. '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 will 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 says. '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 with a prepared with a few examples of times you successfully overcame significant professional challenges.

How do you define success?

What do they ask this? 'Interviewers ask this to see what makes you tick, but to some degree, also to test your mettle,' Taylor says. Your answer gives them insight into your priorities: are you motivated by big paychecks? Being challenged? Learning new skills? 'Or,' she asks, '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 says. '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 says. A good response? 'Applying my brand expertise to the strategic marketing goals you've established for XYZ company, building on your existing success.'

'That's in contrast to a thinly veiled: 'Being in your amazing position, thus freeing you up to do way more important things,'' says Taylor. Stay specific, and stay job-related.

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