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Trick questions cut through "interview clutter" to get to the "raw you."

17 interview questions that aredesigned to trick youJACQUELYN SMITH AND RACHEL SUGARJUN. 29, 2015, 10:01 AM

Savvyhiringmanagerscan glean aton 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 getyou to reveal information you may have been trying to conceal. In other words: they'retrick questions.

"To uncover areas that may reflect inconsistencies, hiring managers sometimes ask thesetricky questions," says Tina Nicolai, executive career coach and founder of ResumeWriters' Ink.

But they're not just about exposing your flaws, says Lynn Taylor, a national workplaceexpert and the author of "Tame Your Terrible Office Tyrant: How to Manage Childish

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Boss Behavior and Thrive in Your Job." These types of questions can help hiringmanagers break through the "traditional interview noise and clutter," and get to the "rawyou."

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

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How would you describe yourself in one word?Why do they ask this? Thequestion is likely being asked toelicit several data points: yourpersonality type, how confidentyou are in your self perception,and whether your work style is agood fit for the job, Taylorexplains.

What makes it tricky? Thisquestion can be a challenge,particularly early on in theinterview, because you don'treally know what personalitytype the manager is seeking."There is a fine line betweensounding self­congratulatoryversus confident, and humbleversus timid," Taylor says."And people are multifaceted,so putting a short label on oneself can seem nearly impossible."

What response are they looking for? Proceed cautiously, warns Taylor. "If you know you'rereliable and dedicated, but love the fact that your friends praise your clever humor, stick with theconservative route." If you're applying for an accounting job, the one word descriptor should notbe "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. However, it would be a mistake to rattle off adjectives that youthink will be well received. This is your opportunity to describe how your best attributes are agreat match for the job as you see it."

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How does this position compare to others you areapplying for?Why do they ask this? They'rebasically asking: "Are youapplying for other jobs?" "Thehiring manager is first trying tofigure out how active you are inyour job search," Nicolai says.Then, once you open up, theywant to see how to speak aboutother companies or positionsyou're interested in — and howhonest you are.

What makes it tricky? If yousay, "This is the only job I'mapplying for," that'll send up ared flag. Very few jobapplicants 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 favorablyabout them, the hiring manager may worry that you'll end up taking another job elsewhere, andthey won't want to waste their time. "Speaking negatively about other jobs or employers isn'tgood either," she says.

What response are they looking for? It is appropriate to say, "There are several organizationswith whom I am interviewing, however, I've not yet decided the best fit for my next careermove." "This is positive and protects the competitors," says Nicolai. "No reason to pit companiesor to brag."

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Can you name three of your strengths and weaknesses?Why do they ask this? Theinterviewer is looking for redflags and deal breakers, such asinability to work well withcoworkers and/or an inability tomeet deadlines. "Each job hasits unique requirements, so youranswers should showcaseapplicable strengths, and yourweaknesses should have a silverlining," Taylor says. "At thevery least, you should indicatethat negative attributes havediminished because of positiveactions you've taken."

What makes it tricky? You can sabotage yourself addressing either. Exposing your weaknessescan hurt you if not ultimately turned into positives, she says. "Your strengths may not align withthe skill set or work style required for the job. It's best to prepare for this question in advance, orrisk landing in a minefield."

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

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Why do you want to work here?Why do they ask this?Interviewers ask this becausethey want to know what drivesyou the most, how well you'veresearched them, and how muchyou want the job.

What makes it tricky?"Clearly you want to work forthe firm for several reasons,"Taylor says. "But just how youprioritize them reveals a lotabout what is important to you."You may be thinking toyourself, "I'm not getting paidwhat I'm worth," or, "I have aterrible boss," or, "All thingsbeing equal, this commute isincredibly short" — none of which endears you to the hiring manager. "You're also being testedon 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 toresearch 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 acan­do attitude; that you are high energy; that you can make a significant contribution; that youunderstand their mission and goals; and that you want to be part of that mission.

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Why do you want to leave your current job?Why do they ask this? "Yourprospective boss is looking forpatterns or anything negative,especially if your positions aremany and short­term," Taylorexplains. They may try todetermine if you currently haveor had issues working withothers leading to termination, ifyou get bored quickly in a job,or other red flags.

What makes it tricky? No onelikes talking about a job theydislike and why. If not answereddiplomatically, your answercould 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 challengingposition that is a better fit for your current skill set. "Know that hiring managers don't mindhearing that you're particularly excited about the growth opportunity at their company."

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What are you most proud of in your career?Why do they ask this?Interviewers ask this becausethey want to understand whatyou're passionate about, whatyou feel you excel at, andwhether you take pride in yourwork. "How you describe yourfavorite project, for example, isalmost as important as theproject itself," Taylor says. "It'sassumed that if you can speakwith conviction and pride aboutyour past work, you can do thesame during importantpresentations at the newemployer."

What makes it tricky? Managers may assume that this type of work is what you really want todo most or focus on in the future. It can make you sound one­dimensional if you don't put it in thecontext of a larger range of skills and interests.

What response are they looking for? Hiring managers want to see your ability to articulatewell, foster enthusiasm in others, and your positive energy. "But one note of caution: In all yourzeal to share your successes, remain concise," Taylor suggests. "You want to showcase yourability to present well once on the job."

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What kind of boss and coworkers have you had the mostand least success with, and why?Why do they ask this?Interviewers are trying toascertain if you generally haveconflicts with people and/orpersonality types. "Secondarily,they want to know how you canwork at your best," says Taylor.

What makes it tricky? Yourun the risk of appearingdifficult by admitting tounsuccessful interactions withothers, unless you keepemotions out of it. You mayalso inadvertently describesome of the attributes of yourprospective boss. If you say, "Ihad a boss who held so many meetings that it was hard to get my work done," and yourinterviewer turns beet red — you might have hit a nerve.

What response are they looking for? "They want to hear more good than bad news," Taylorexplains. "It's always best to start out with the positive and downplay the negatives." You don'twant 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 appearflexible enough to work with a variety of personality types. For example: "I think I work wellwith a wide gamut of personalities. Some of my most successful relationships have been whereboth people communicated very well and set mutual expectations upfront."

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Have you ever considered being an entrepreneur?Why do they ask this? Theinterviewer is testing to see ifyou still have the hidden desireto run your own company, thusabandoning ship, Taylor says."No firm wants to sense this, asthey will begin to ponderwhether their valuable trainingtime and money could vanish."

What makes it tricky? Mosteveryone has considered beingan entrepreneur at some point intheir lives, but to varyingdegrees. This question is trickybecause you can unwittingly belured into talking about yourone­time desire to be your own boss with too much perceived enthusiasm. An employer may fearthat you still hope to eventually go out on your own, and they'll consider you a flight risk.

What response are they looking for? It's okay to tell a prospective manager that you onceconsidered entrepreneurship or have worked as an independent contractor. It can easily be turnedinto a positive by stating that you've already experienced it or thought about it, and it's not foryou. 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 ismost fulfilling to you. You may also enjoy the specialized work in your field more than theoperational, financial, or administrative aspects of entrepreneurship. You can further allay theirfears by explaining exactly why their company appeals to you.

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If you could work for any company, where would youwork?Why do they ask this? Hiringmanagers want to ascertain howserious you are about workingfor them in particular, versus thecompetition, as well as yourlevel of loyalty, Taylor says. "Italso helps them weed outcandidates who may veer fromthe core career. You may haveheard that Google is a greatplace to work, but that off­roadstrategy would spell doom, asyou're being given theopportunity to theoreticallywork at your 'dream job.' Theinterviewer 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 andinadvertently leak out some well­respected firms, but this is counterproductive and only instillssome doubt about your objectives.

What are they seeking? "Your interviewer wants to know that you're interviewing at your firstcompany of choice." A response to this might be, "Actually, I've been heavily researching targetfirms, and [your company] seems like the ideal fit for my credentials. It's exciting to me that [yourcompany] is doing XYZ in the industry, for example, and I'd like to contribute my part."

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What would you do if you won $5 million tomorrow?Why do they ask this? Theywant to know whether you'dstill work if you didn't need themoney. Your response to thisquestion tells the employerabout your motivation and workethic. They may also want toknow what you'd spend themoney on, or whether you'dinvest it. This tells them howresponsible you are with yourmoney, and how mature you areas a person.

What makes it tricky?Questions that are out of left field can ambush you, causing you to lose composure. "They havenothing to do with the job at hand, and you may wonder if there is any significance to them,"Taylor says. "Whether there is or not, the fact remains that you can easily lose your cool if youdon'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'd continue working becauseyou're passionate about what you do — and they want to know you'd make smart financialdecisions. If you'd do something irresponsible with your own money, they'll worry you'llbe careless with theirs.

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Have you ever been asked to compromise your integrityby your supervisor or colleague? Tell us about it.Why do they ask this? Yourprospective boss is evaluatingyour moral compass. They wantto know how you handled adelicate situation that put yourintegrity to the test, Taylorexplains. "They may also digtoo deeply to test your level ofdiscretion." Essentially theywant to know: Did you usediplomacy? Did you publiclyblow the whistle? Did abacklash ensue? What was yourthought process?

What makes it tricky? Interviewers want to know how you manage sensitive matters, and arealso wary of those who badmouth former employers, no matter how serious the misdeed. "Theywill be concerned if you share too much proprietary information with the interviewer," she says."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 youranswer, without revealing any internal practices of prior employers. "You have nothing to gain bydivulging private corporation information."

Something like this might work: "There was one time where a fellow worker asked me to getinvolved in a project that seemed unethical, but the problem resolved itself. I try to be as honestas possible early on if a project creates concern for me about the company, as I'm very dedicatedto its success."

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Can you give us a reason someone may not like workingwith you?Why do they ask this?Prospective bosses want toknow if there are any glaringpersonality issues, and whatbetter way that to go direct tothe source? "They figure thatthe worst that can happen is youwill lie, and they may feelthey're still adept at detectingmistruths," Taylor explains."The negative tone of thequestion is bound to test themettle of even the mostseasoned businessprofessionals."

What makes it tricky? You can easily shoot yourself in the foot with this question. If you're flipand say, "I can't think of a reason anyone wouldn't like working with me," you're subtly insultingthe interviewer by trivializing the question. So you have to frame the question in a way that getsat the intent without being self­effacing. "Hiring managers are not seeking job candidates whohave self­pity," she says.

What response are they looking for? You don't want to say, "Well I'm not always the easiestperson 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 thepositive and go from there: 'Generally I've been fortunate to have great relationships at all myjobs. The only times I have been disliked — and it was temporary — was when I needed tochallenge my staff to perform better. Sometimes I feel we must make unpopular decisions that arefor the larger good of the company,'" 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 theperceived skeletons in the closethave been removed." This is adaunting question in particularbecause it can seem offensive.The implication is that youmight not be motivated enoughto secure a job; you are beingdistracted by other pursuits;your skills set may not be up todate; there is an issue with yourpast employers, or a host of other concerns.

What makes it tricky? The way it's worded is naturally designed to test your resilience. The keyis 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 be assured that you possessinitiative even when unemployed, as this drive and tenacity will translate well in a corporatesetting. Sample responses: "I have been interviewing steadily, but want to find the ideal fit beforeI jump in and give my typical 110%," or, "I'm active in my job search, and I keep my skillscurrent through [courses, volunteering, social media, business networking groups]." "If you tookoff time to take care of a personal matter, you can certainly state that without giving a lot ofdetail," Taylor says.

Make sure you're accountable. Don't blame the unemployment rate, your market, industry, oranything else. This is about how active and excited you are to be making a contribution to theemployer.

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How did you make time for this interview? Where doesyour boss think you are right now?Why do they ask this? Hiringmanagers want to find out ifyour priorities are in the rightplace: current job first,interviews second. "They knowthat the habits you follow nowspeak to your integrity and howyou will treat your job at theircompany should you undertakea future job search," saysTaylor. "They also want toknow how you handle awkwardsituations where you cannot betruthful to your boss. Ideallyyour interview is during a breakthat is your time, which is important to point out."

What makes it tricky? The implication is, "How is it searching for a job behind your boss'sback?" For most employed job seekers, it's uncomfortable to lie about their whereabouts. Sothey'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, andschedule interviews before or after work, at lunchtime, during weekends if appropriate, andduring personal time off. If asked pointedly, "Where does your boss think you are right now?" bevague. Don't say: "I took a sick day." Instead, Taylor suggests you try something like: "My bossunderstands that I have certain break periods and personal time — he doesn't ask for details. He'smost interested in my results."

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What's a difficult situation that you turned around?Describe it to us.What do they ask this? Thisgives hiring managers a lot ofinformation in one fell swoop,explains Taylor. They want toknow "not only know how youhandle stressful situations, butalso how you think throughproblems, how you define'difficult,' and what courses ofaction you take when faced withany form of adversity."

What makes it tricky? It's easyto interpret this as an invitationto brag about the success ofyour turnaround. Don't fall forit. "The emphasis is really onhow you generally problem­solve under pressure," Taylor explains. "Do you illustrate any signsof 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, sincethey'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 problemsolver, Taylor says. "They place a premium on those who can think clearly, remain professionalwhen under the gun — and those who can recover quickly from setbacks." To ace the question, besure you go into the meeting with a prepared with a few examples of times you successfullyovercame significant professional challenges.

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You’ve worked for yourself for a number of years. Howdo you plan on acclimating to our company culture vs.being your own boss?Why do they ask this? Ifyou've spent time as your ownboss, you've almost certainlypicked up skills that wouldmake you an asset to theorganization. But Nicolai saysthat your entrepreneurial pastcan make you intimidating tosome hiring managers, who mayquestion your commitment totheir cause. "Many employers,particularly those who havenever been their own boss, tendto shy away from individualswho have worked forthemselves," she observes.

What makes this tricky? Toprove that you're not"intimidating" or "threatening,"you can be tempted to water down your achievements — but underplaying your skills is generallynot the best way to prove you're the best for the job.

What response are they looking for? "The employer is looking for the candidate to talk aboutcommitment to the company and expressing a desire to become part of a larger team where thecandidate can make a contribution," Nicolai advises. If even any part of you misses being part ofa larger organization, now's the time to stress it. "The employer wants to be needed by thecandidate," she says. Accordingly, this is an opening to express how much you want the gig.

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How do you define success?What do they askthis? "Interviewers ask this tosee what makes you tick, but tosome degree, also to test yourmettle," Taylor says. Youranswer gives them insight intoyour priorities: are youmotivated by big paychecks?Being challenged? Learningnew skills? "Or," she asks, "doyou take a more personal,individualistic approach tosuccess?"

What makes it tricky? Thisone is a minefield, since "success" is highly subjective, and even a perfectly reasonable responsecan be easily misinterpreted, Taylor says. "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 advanceand make a difference.'"

What response are they looking for? When questions are broad and leave a lot of room for "avirtual inquisition," Taylor advises keeping your answers relatively unobjectionable. "Try todefine success in a way that relates to the prospective employer, based on what you know fromthe job description and conversation," she says. A good response? "Applying my brand expertiseto the strategic marketing goals you’ve established for XYZ company, building on your existingsuccess."

"That’s in contrast to a thinly veiled: 'Being in your amazing position, thus freeing you up to doway more important things,'" says Taylor. Stay specific, and stay job­related.

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