If they're going to cheat, we'll help you cheat right back.

    • Interview questions are often designed to test candidates.
    • Some of these questions are obviously difficult, while others are more subtle traps.
    • Business Insider spoke to two career experts who listed some especially tricky questions to watch out for and how to answer them.


    Savvy hiring managers know exactly what to ask candidates.

    Sometimes, that means asking prospective employees seemingly simple questions.

    These questions may seem innocuous at first, but they're actually trying to get you to reveal information you may have been trying to conceal. Hiring managers often love these queries. Used correctly, they break through the traditional interview noise and clutter to get to the raw you.

    So it's important to learn how to answer questions designed to trick you.

    Here are a few particularly thorny questions — and some suggestions on how to answer them:

    'Can you tell me about yourself?'

    "The employer wants to hear that the candidate did their homework," Tina Nicolai, executive career coach and founder of Resume Writers' Ink, told Business Insider. "The interviewer is also listening for a level of confidence in how well the candidate portrays herself through the information that is communicated."

    So, how can such a straightforward question be a trap? Nicolai said that it's important not to use this question as an opportunity to chat about your personal life. You need to focus on your potential value to the organisation.

    "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.

    Remember, what we tell people about us is what they hear. So stay sharp and convey your top strengths when answering this question.



    'How would you describe yourself in one word?'

    With this question, interviewers are likely hoping to elicit several data points.

    They want to know about your personality type, how confident you are in your self perception, and whether your work style is a good fit for the job, explained Lynn Taylor, a national workplace expert and the author of "Tame Your Terrible Office Tyrant: How to Manage Childish Boss Behavior and Thrive in Your Job

    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 told Business Insider. "And people are multifaceted, so putting a short label on oneself can seem nearly impossible."

    When in doubt, opt for the conservative route. For example, if your coworkers find you both hilarious and reliable, Taylor said to stay on the safe side and emphasise the latter trait.

    But most of all, try to tailor your response to the role or organisation in question.

    "Most employers today are seeking team players that are levelheaded under pressure, upbeat, honest, reliable, and dedicated," she added. "However, it would be a mistake to rattle off adjectives that you think will be well received. This is your 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?'

    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 said. The interviewer wants to see how you speak about other companies or positions that hold your interest — and how honest you are. 

    If you say, "This is the only job I'm applying for," that'll send up a red flag. Very few job applicants apply to only one job — so they may assume you're being dishonest.

    If you openly speak about other positions you're pursuing, however, and you speak favorably about them, the hiring manager may see you as unattainable and pass.

    "Speaking negatively about other jobs or employers isn't good either," she said.

    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," Nicolai said. "No reason to pit companies or to brag." 



    'Can you name three of your strengths and weaknesses?'

    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."

    Exposing your weaknesses can hurt you if not ultimately turned into positives, she 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," Taylor said.

    And, as for strengths, Hiring managers want to know that they will be a direct asset to the new position.

    But the most important thing is to be able to show the interviewer that you're capable of well-thought-out self-reflection.

    "They are also looking for your ability to self-assess with maturity and confidence," Taylor said.



    'Why do you want to work here?'

    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.

    "Clearly you want to work for the firm for several reasons," Taylor said. "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 said.

    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?'

    "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.

    So tread with caution. If you're not diplomatic, your answer could raise further questions and doubts or sink your chances entirely.

    The hiring manager is likely hoping you are seeking a more challenging position that is a better fit for your skill set, according to Taylor.

    "Know that hiring managers don't mind hearing that you're particularly excited about the growth opportunity at their company," Taylor said.



    'What are you most proud of in your career?'

    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."

    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.

    Hiring managers want to see your ability to articulate well and foster enthusiasm in others, as well as your positive energy.

    "But one note of caution: In all your zeal to share your successes, remain concise," Taylor said. "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?'

    The key to answering this question is staying cool.

    You run the risk of appearing difficult by admitting to unsuccessful interactions with others, unless you keep emotions out of it.

    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," Taylor said. 

    You may also inadvertently describe some of the attributes of your prospective boss. 

    "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.

    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 up front."  


    'Have you ever considered being an entrepreneur?'

    In most cases, this question gets at whether or not you're planning to abandon ship and found your own company, Taylor said.

    "No firm wants to sense this, as they will begin to ponder whether their valuable training time and money could vanish," Taylor said.

    Don't get 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.

    It's okay to tell a prospective manager that you once considered entrepreneurship or have worked as an independent contractor.

    Turn the experience into a positive by saying that you've already experienced it or thought about it, and it's not for 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.

    You may also enjoy the specialised work in your field more than the operational, financial, or administrative aspects of entrepreneurship.

    You can further allay their fears by explaining exactly why their company appeals to you.



    'If you could work for any company, where would you work?'

    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.

    "It also helps them weed out candidates who may veer from the core career," Taylor said. "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.'"

    Basically, stay focused on the job at hand. Don't get caught up in the casual flow of the discussion and inadvertently leak out your preference for a well-known firm.

    "Your interviewer wants to know that you're interviewing at your first company of choice," Taylor said.

    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," Taylor said. "It's exciting to me that [your company] is doing XYZ in the industry, for example, and I'd like to contribute my part."



    'Why were you retrenched?'

    "Employers want to know how you hold up under pressure and less fortunate circumstances such as job loss," Nicolai said. "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."

    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 added.

    Instead, talk about the business decision behind the layoff and keep your own feelings about the situation in check.

    "Be sure to not cast blame or any discontent," Nicolai said. "Stay on track with the facts as you know them."


    'What would you do if you won R50 million tomorrow?'

    What's the goal of this out-of-left-field question? The interviewer probably wants to know whether you would still work if you did not need the money.

    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.  Your response to this question tells the employer about your motivation and work ethic.

    Your interviewer also might be testing your ability to handle a somewhat random question.

    "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."



    'Have you ever been asked to compromise your integrity by your supervisor or colleague? Tell us about it.'

    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," she said.

    Essentially they want to know: Did you use diplomacy? Did you publicly blow the whistle? Did a backlash ensue? What was your thought process?

    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," she said. "So it is tricky because you must carefully choose your words, using the utmost diplomacy."

    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," Taylor said.  


    'Can you give us a reason someone may not like working with you?'

    Prospective bosses want to know if there are any glaring personality issues, and what better way than 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 mis-truths," Taylor said. "The negative tone of the question is bound to test the mettle of even the most seasoned business professionals."

    But be careful. 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 trivialising 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 said.

    Taylor suggested leading with the positive: "'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,'" Taylor added. "'Sometimes I feel we must make unpopular decisions that are for the larger good of the company.'"



    'How did you make time for this interview? Where does your boss think you are right now?'

    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."

    The implication is, "How is it searching for a job behind your boss' back?" 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.

    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.

    If asked pointedly, "Where does your boss think you are right now?" be vague.

    Don't say: "I took a sick day." Instead, Taylor suggested you 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."


    'Tell me about a time you disagreed with a company policy'

    The hiring manager is attempting to determine a number of things with this query.

    Namely, your decision-making ability, ease of working with others, and most importantly, whether you will speak up after identifying an area in need of improvement.

    "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."

    While companies want leaders and employees to follow the rules, 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.

    So offer up a real situation that points out a logical and business reason that you were in opposition of a policy, she suggested.

    "Focus on how your idea to rework the policy was beneficial to the company as a whole," Nicolai said. "Speak up on the research that you conducted, the facts that you presented, and the outcome of your attempts to have the policy rewritten."

    Jacquelyn Smith contributed to a previous version of this article.