JOB SEARCH

21 job interview questions that are

designed to trick you
Rachel Premack and Jacquelyn Smith October 25, 2018

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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 re ect 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 aws, said Lynn Taylor, a national
workplace expert and the author of “Tame Your Terrible O ce Tyrant.”

“Their real agenda is for your answers to ultimately paint a picture that you are the
perfect t 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 con dently 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.”

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 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 con dent you are in your self-perception, and
whether your work style is a good t 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 ne line between sounding self-congratulatory versus
con dent, and humble versus timid,” Taylor said. “And people are multifaceted, so
putting a short label on oneself can seem nearly impossible.”

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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
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best t 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 ags 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 mine eld.”

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 con dence,” 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 rm for several reasons,”
Taylor said. “But just how you prioritize them reveals a lot about what is important to
you.”

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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 ags.

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 t for your skill set or that there’s something speci c 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?

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desire to run your own company, thus abandoning ship, Taylor said. “No rm 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 ight 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 ful lling to you. You may also enjoy the specialized work in your eld
more than the operational, nancial, 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 o ce
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
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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
con icts with people and/or personality types, Taylor said.

What makes it tricky? You run the risk of appearing di cult 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 exible 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 ow of the discussion
and inadvertently leak out some well-respected rms, but this is counterproductive
and only instills some doubt about your objectives.
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 What response are they looking for? “Your interviewer wants to know that you’re
interviewing at your rst company of choice,” Taylor said.

Try this response: “Actually, I’ve been heavily researching target rms, and (your
company] seems like the ideal t 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
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added, “do you take a more personal, individualistic approach to success?”

What makes it tricky? This one is a mine eld, since “success” is highly subjective,
and even a perfectly reasonable response can be easily misinterpreted, Taylor said.
“There’s a ne line between sounding ambitious and appearing as if you’re eyeing the
top spot in the o ce — 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 de ne 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?

Facebook
Why do they ask this? Reed wrote that the interviewer is really asking, “Is there
Flipboard 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
LinkedIn
yourself — and others?”
Email
What makes it tricky? “Regret is a loaded word: don’t point it your way,” Reed wrote.
Pocket
What response are they looking for? Reed suggested giving the interviewer “a little
Twitter bit of grit,” but says you should try to avoid using the word “regret.”

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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 con dence — 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 nger 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
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 What makes it tricky? Questions that are out of left eld 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 signi cance 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 nancial 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.”

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 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
gure 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 ip 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.

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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 nd the ideal t
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 bene cial to the company as a
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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 nd out if your priorities are in the
right place: current job rst, 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
rst, 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.”

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Black this week.

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 de ne ‘di cult,’ 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 “di cult.”

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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 signi cant professional challenges.

This article rst appeared on Business Insider.

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