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19 interview questions that are designed totrick you

JACQUELYN SMITHMAY 6, 2016, 10:00 AM

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Savvy hiring managers can glean a ton of information about you by asking just a few, well­chosen questions.

But while they may seem simple — that's the point — some are actually designed to get you to reveal informationyou 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 authorof "Tame Your Terrible Office Tyrant: How to Manage Childish Boss Behavior and Thrive in Your Job." Thesetypes of questions can help hiring managers break through the "traditional interview noise and clutter," and getto the "raw you."

Here are 19 common examples, complete with advice on how to ace each one.

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Can you tell me about yourself?Why do they ask this? They ask to determine how thecandidates see themselves as it pertains to the position."The employer wants to hear that the candidate did theirhomework," says Nicolai. "The interviewer is alsolistening for a level of confidence in how well thecandidate portrays herself through the information that iscommunicated. Additionally, the interviewer is listeningfor strong behavioral competencies, which help determinea right fit with the job. If this opening answer is weak, itcan send the remainder of the interview into a tailspin orcut the interview short."

What makes it tricky? It can tempt you to talk about yourpersonal life — which you shouldn't! "Most candidates arenot versed in seeing this as a trick question, so they mayanswer by speaking from a personal perspective: 'I havethree kids, I'm married, etc,'" Nicolai says. "Believe it ornot, even the most seasoned candidate falls for thisquestion especially when prompted by the interviewer to elaborate."

What response are they looking for? A focused, laser­sharp answer conveying your value to the organization anddepartment. "The employer wants to hear about your achievements broken down into two or three succinct bullet answersthat will set the tone of the interview," she says. Remember, what we tell people about us is what they hear. So stay sharpand convey your top strengths when answering this question.

For example, you can try something like: "I am known for turning around poor performance teams as a result of my innateskills in analyzing problems and seeing solutions very quickly." This statement tells the interviewer that the candidate hasanalytical skills, problem­solving ability, and leadership ability to turnaround business performance, among other things.

"At least four behavioral skills are conveyed in this simple response, and it sets the tone for the interviewer to ask moretargeted questions," Nicolai says.

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How would you describe yourself in one word?Why do they ask this? This will most likely come up toelicit several data points: your personality type, howconfident you are in your self perception, and whetheryour work style is a good fit for the job, explains Taylor.

What makes it tricky? This question can be a challenge,particularly early on in the interview, because you don'treally know what personality type the manager is seeking."There is a fine line between sounding self­congratulatoryversus confident, and humble versus timid," Taylor says."And people are multifaceted, so putting a short label ononeself can seem nearly impossible."

What response are they looking for? Proceed cautiously,Taylor warns. "If you know you're reliable and dedicated,but love the fact that your friends praise your cleverhumor, stick with the conservative route."

If you're applying for an accounting job, the one­worddescriptor 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, anddedicated," she adds. "However, it would be a mistake to rattle off adjectives that you think will be well received. This isyour opportunity to describe how your best attributes are a great match for the job as you see it."

How does this position compare to others you are applying for?Why do they ask this? They're basically asking: "Are youapplying for other jobs?" "The hiring manager is firsttrying to figure out how active you are in your job search,"Nicolai says. The interviewer wants to see how you speakabout other companies or positions that hold your interest— and how honest you are.

What makes it tricky? If you say, "This is the only jobI'm applying for," that'll send up a red flag. Very few jobapplicants apply to only one job — so they may assumeyou're being dishonest. If you openly speak about otherpositions you're pursuing, however, and you speakfavorably about them, the hiring manager may see you asunattainable and pass. "Speaking negatively about otherjobs or employers isn't good either," she says.

What response are they looking for? It is appropriate tosay, "There are several organizations with whom I aminterviewing, however, I've not yet decided the best fit for my next career move."

"This is positive and protects the competitors," Nicolai says. "No reason to pit companies or to brag."

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Can you name three of your strengths and weaknesses?Why do they ask this? The interviewer is looking for redflags and deal­breakers, such as an inability to work wellwith coworkers or an inability to meet deadlines.

"Each job has its unique requirements, so your answersshould showcase applicable strengths, and yourweaknesses should have a silver lining," Taylor says. "Atthe very least, you should indicate that negative attributeshave diminished because of positive actions you've taken."

What makes it tricky? You can sabotage yourselfaddressing either. Exposing your weaknesses can hurt youif not ultimately turned into positives, she says. "Yourstrengths may not align with the skill set or work stylerequired for the job. It's best to prepare for this question inadvance, or risk landing in a minefield."

What response are they looking for? Hiring managers want to know that your strengths will be a direct asset to the newposition and none of your weaknesses would hurt your ability to perform. "They are also looking for your ability to selfassess with maturity and confidence," Taylor says.

Why do you want to work here?Why do they ask this? Interviewers ask this because theywant to know what drives you the most, how well you'veresearched them, and how much you want the job.

What makes it tricky? "Clearly you want to work for thefirm for several reasons," Taylor says. "But just how youprioritize them reveals a lot about what is important toyou."

You may be thinking to yourself, "I'm not getting paidwhat I'm worth," or, "I have a terrible boss," or, "All thingsbeing equal, this commute is incredibly short" — none ofwhich endears you to the hiring manager.

"You're also being tested on your level of interest for thejob," she says.

What response are they looking for? Hiring managerswant to see that you've taken the time to research thecompany and understand the industry.

They also want to know that you actually want this job (and not just any job); that you have a can­do attitude; that you arehigh energy; that you can make a significant contribution; that you understand their mission and goals; and that you want tobe part of that mission.

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Why do you want to leave your current job?Why do they ask this? "Your prospective boss is lookingfor patterns or anything negative, especially if yourpositions are many and short­term," Taylor says. Theinterviewer may try to determine whether you have hadissues working with others leading to termination, if youget 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 orsink your chances entirely.

What response are they looking for? They hope you areseeking a more challenging position that is a better fit foryour skill set. "Know that hiring managers don't mindhearing that you're particularly excited about the growthopportunity at their company."

What are you most proud of in your career?Why do they ask this? Interviewers want to understandwhat 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, isalmost as important as the project itself," Taylor says. "It'sassumed that if you can speak with conviction and prideabout your past work, you can do the same duringimportant presentations at the new employer."

What makes it tricky? Managers may assume that thistype of work is what you really want to do most or focuson in the future. It can make you sound one­dimensional ifyou don't put it in the context of a larger range of skills andinterests.

What response are they looking for? Hiring managerswant to see your ability to articulate well and foster enthusiasm in others, as well as your positive energy. "But one note ofcaution: In all your zeal to share your successes, remain concise," Taylor says. "You want to showcase your ability to presentwell once on the job."

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Have you ever considered being an entrepreneur?Why do they ask this? The interviewer is testing to see ifyou still have the hidden desire to run your own company,thus abandoning ship, Taylor says. "No firm wants to sensethis, as they will begin to ponder whether their valuabletraining time and money could vanish."

What makes it tricky? Most everyone has consideredbeing an entrepreneur at some point in their lives, but tovarying degrees. This question is tricky because you canunwittingly be lured into talking about your one­timedesire to be your own boss with too much perceivedenthusiasm. An employer may fear that you still hope toeventually go out on your own and consider you a flightrisk.

What response are they looking for? It's OK to tell aprospective manager that you once consideredentrepreneurship or have worked as an independentcontractor. It can easily be turned into a positive by saying that you've already experienced it or thought about it, and it's notfor you. 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. Youmay also enjoy the specialized work in your field more than the operational, financial, or administrative aspects ofentrepreneurship. You can further allay their fears by explaining exactly why their company appeals to you.

What kind of boss and coworkers have you had the most and leastsuccess with, and why?Why do they ask this? Interviewers are trying to ascertainif you generally have conflicts with people and/orpersonality types. "Secondarily, they want to know howyou can work at your best," Taylor says.

What makes it tricky? You run the risk of appearingdifficult by admitting to unsuccessful interactions withothers, unless you keep emotions out of it. You may alsoinadvertently describe some of the attributes of yourprospective boss. If you say, "I had a boss who held somany meetings that it was hard to get my work done," andyour interviewer turns beet red — you might have hit anerve.

What response are they looking for? "They want to hearmore good than bad news," Taylor says. "It's always bestto start out with the positive and downplay the negatives."You don't want to be evasive, but this is not the time tooutline all your personality shortcomings either. This is an opportunity to speak generally about traits that you admire inothers 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 beenwhere both people communicated very well and set mutual expectations up front."

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If you could work for any company, where would you work?Why do they ask this? Hiring managers want to ascertainhow 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 whomay veer from the core career. You may have heard thatGoogle is a great place to work, but that off­road strategywould spell doom, as you're being given the opportunity totheoretically work at your 'dream job.' The interviewer isn'tmaking conversation here, so stay focused on the job athand."

What makes it tricky? You might get caught up in thecasual flow of the discussion and inadvertently leak outsome well­respected firms, but this is counterproductiveand 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." Aresponse to this might be, "Actually, I've been heavily researching target firms, and [your company] seems like the ideal fitfor my credentials. It's exciting to me that [your company] is doing XYZ in the industry, for example, and I'd like tocontribute my part."

How do you define success?Why do they ask this? "Interviewers ask this to see whatmakes you tick, but to some degree, also to test yourmettle," Taylor says. Your answer gives them insight intoyour priorities: are you motivated by big paychecks? Beingchallenged? Learning new skills? "Or," she asks, "do youtake a more personal, individualistic approach to success?"

What makes it tricky? This one is a minefield, since"success" is highly subjective, and even a perfectlyreasonable response can be easily misinterpreted, Taylorsays. "There’s a fine line between sounding ambitious andappearing as if you’re eyeing the top spot in the office — because you 'really want to advance and make adifference.'"

What response are they looking for? When questions are broad and leave a lot of room for "a virtual inquisition," Tayloradvises keeping your answers relatively unobjectionable. "Try to define success in a way that relates to the prospectiveemployer, based on what you know from the job description and conversation," she says. A good response? "Applying mybrand 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 importantthings,'" says Taylor. Stay specific, and stay job­related.

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Why were you laid off?Why do they ask this? "Employers want to know howyou hold up under pressure and less fortunatecircumstances such as job loss," Nicolai says. "They wantto hear that you are positive and ready to get back to workwith a great attitude. They also want to hear a level ofconfidence — not defeat or anger."

What makes it tricky? For starters, you may be bitter orangry about the layoff, and this question may prompt youto bad­mouth your former employer, which you neverwant to do in a job interview.

"Stay away from finger pointing, desperation, orportraying a victim," she adds.

What response are they looking for? "Provide a level­headed answer that is focused on a business decision bythe company to conduct the layoff," Nicolai says. "Be sureto not cast blame or any discontent. Stay on track with thefacts as you know them."

What would you do if you won $5 million tomorrow?Why do they ask this? They want to know whether youwould still work if you did not need the money. Yourresponse to this question tells the employer about yourmotivation and work ethic. The interviewer may also wantto know what you would spend the money on or whetheryou would invest it. This illustrates how responsible youare with your money and how mature you are as a person.

What makes it tricky? Questions that are out of left fieldcan ambush you, causing you to lose composure. "Theyhave nothing to do with the job at hand, and you maywonder if there is any significance to them," Taylor says."Whether there is or not, the fact remains that you caneasily lose your cool if you don't pause and gather yourthoughts before you respond to a question like this."

What response are they looking for? They want to hearthat you would continue working because you're passionate about what you do — and they want to know you would makesmart financial decisions. If you would do something irresponsible with your own money, they'll worry you'll be carelesswith theirs.

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Have you ever been asked to compromise your integrity by yoursupervisor or colleague? Tell us about it.Why do they ask this? Your prospective boss isevaluating your moral compass by asking how youhandled a delicate situation that put your integrity to thetest, Taylor says. "They may also dig too deeply to testyour level of discretion." Essentially they want to know:Did you use diplomacy? Did you publicly blow thewhistle? Did a backlash ensue? What was your thoughtprocess?

What makes it tricky? Interviewers want to know howyou manage sensitive matters and are also wary of thosewho bad­mouth former employers, no matter how seriousthe misdeed. "They will be concerned if you share toomuch proprietary information with the interviewer," shesays. "So it is tricky because you must carefully chooseyour 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 anyinternal 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 thatseemed unethical, but the problem resolved itself. I try to be as honest as possible early on if a project creates concern forme 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 knowif there are any glaring personality issues, and what betterway than to go direct to the source? "They figure that theworst that can happen is you will lie, and they may feelthey're still adept at detecting mistruths," Taylor says. "Thenegative tone of the question is bound to test the mettle ofeven the most seasoned business professionals."

What makes it tricky? You can easily shoot yourself inthe foot with this question. If you flip and say, "I can'tthink of a reason anyone wouldn't like working with me,"you're subtly insulting the interviewer by trivializing thequestion. So you have to frame the question in a way thatgets at the intent without being self­effacing. "Hiringmanagers are not seeking job candidates who have self­pity," 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 thenearest exit. "Conversely, you can lead with the positive and go from there: 'Generally I've been fortunate to have greatrelationships at all my jobs. The only times I have been disliked — and it was temporary — was when I needed to challengemy staff to perform better. Sometimes I feel we must make unpopular decisions that are for the larger good of thecompany,'" Taylor suggests.

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Why have you been out of work for so long?Why do they ask this? "Interviewers are skeptical bydesign," Taylor says. "Sometimes you're guilty untilproven innocent — until all the perceived skeletons in thecloset have been removed." This is a daunting question inparticular because it can seem offensive.

The implication is that you might not be motivated enoughto secure a job; you are being distracted by other pursuits;your skills set may not be up to date; there is an issue withyour past employers, or a host of other concerns.

What makes it tricky? The way it's worded is naturallydesigned to test your resilience. The key is not to take thebait and just answer the intent of the question in a calm,factual manner.

What response are they looking for? The hiring managerwants be assured that you possess initiative even when unemployed, as this drive and tenacity will translate well in acorporate setting.

Sample responses: "I have been interviewing steadily, but want to find the ideal fit before I jump in and give my typical110%," or, "I'm active in my job search, and I keep my skills current through [courses, volunteering, social media, businessnetworking groups]." "If you took off time to take care of a personal matter, you can certainly state that without giving a lotof detail," Taylor says.

Make sure you're accountable. Don't blame the unemployment rate, your market, industry, or anything else. This is abouthow 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 decision­making ability, ease of working with others, and mostimportantly, whether the candidate will speak up afteridentifying an area in need of improvement.

What makes it tricky? "To say, 'I've never disagreed witha company policy' is tough to believe from even the mostamenable employee," Nicolai says. "This also sends amessage that you may just accept anything that you aretold to do without thinking through all possible outcomes."While companies want leaders and employees to followthe rules, they also want people who are going to reviewpotential outdated policies and have the courage to pushback and propose changes to maintain a current,competitive edge and productive workplace.

What response are they looking for? Offer up a realsituation that points out a logical and business reason thatyou were in opposition of a policy, she suggests. "Focus onhow 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."

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How did you make time for this interview? Where does your boss thinkyou are right now?Why do they ask this? Hiring managers want to find outif your priorities are in the right place: current job first,interviews second. "They know that the habits you follownow speak to your integrity and how you will treat yourjob at their company should you undertake a future jobsearch," Taylor says. "They also want to know how youhandle awkward situations where you cannot be truthful toyour boss. Ideally your interview is during a break that isyour time, which is important to point out."

What makes it tricky? The implication is, "How is itsearching for a job behind your boss' back?" For mostemployed job seekers, it's uncomfortable to lie about theirwhereabouts. So they're vague and treat it like any otherpersonal matter they handle on their time.

What response are they looking for? It's wise to explainthat you always put your job first, and schedule interviews before or after work, at lunchtime, during weekends ifappropriate, and during personal time off. If asked pointedly, "Where does your boss think you are right now?" be vague.Don't say: "I took a sick day." Instead, Taylor suggests you try something like: "My boss understands that I have certainbreak 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? Describe it to us.What do they ask this? This gives hiring managers a lotof information in one fell swoop, explains Taylor. Theywant to know "not only know how you handle stressfulsituations, but also how you think through problems, howyou define 'difficult,' and what courses of action you takewhen faced with any form of adversity."

What makes it tricky? It's easy to interpret this as aninvitation to brag about the success of your turnaround.Don't fall for it. "The emphasis is really on how yougenerally problem­solve under pressure," Taylor explains."Do you illustrate any signs of stress as you describe theevent? Were you creative, resourceful and prompt in itsresolution? Did you follow a logical path in doing so?"Choose your examples extremely carefully, since they'llgive 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 placea premium on those who can think clearly, remain professional when under the gun — and those who can recover quicklyfrom setbacks." To ace the question, be sure you go into the meeting with a prepared with a few examples of times yousuccessfully overcame significant professional challenges.

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