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25 Job Interview Questions Designed To Stump You

Every so often, interviewers will ask questions that are going to stump you. Whether or not this is their intention, there is nothing worse than a deafening silence in the middle of an interview. To help you out a bit, we have compiled a list of these questions and how you can quickly recover when you’re met with one of them.

1. Can you tell me about yourself?

The interviewers ask these questions in order to determine how the candidates are going to see themselves as it pertains to the position. The key here is to keep your answer professional. Despite the vagueness of the question, interviewers do not want to know about your personal life. The responses they are looking for are focused, laser-sharp answers that will show your value to the organization and department. To perfect this response, the key to it is focusing on positivity and what you bring to the role, rather than why the job might benefit you.

2. How would you describe yourself in one word?

The interviewers ask this question to elicit several data points from you. For example, for your personality type, how confident you are in your perception of one’s self and whether your working style will fit the job. This can be tricky because you don’t really know what the manager is looking for in someone’s personality. Ultimately, this question is asked in order to reveal your true character, so it’s very important to respond with sincerity and to consider what it could say about you. A lot of people have gone to great schools or they have very good connections—perhaps, on paper, they are better than you. This is a good chance to show them what kind of colleague or employee you are going to be and what sets you apart from the crowd. That’s what the interviewers want to invest in.

3. How does this position compare to others you are applying for?

The interviewers ask this question in order to know how active you are in your job search. You should openly speak about other positions you are pursuing, but you should not give too much away. An appropriate answer to this question is something along the lines of, “[…] There are several organizations with whom I am interviewing, however, I’ve not yet decided the best fit for my next career move.”

4. Can you name three of your strengths and weaknesses?

The interviewers ask this question to look for red flags and deal-breakers; such as not being able to work well with others, or an inability to meet deadlines. Keep in mind that exposing your weaknesses can hurt you, but it can also be made into a positive thing. They want to know that your strengths would be a great asset for the new position and that none of your weaknesses would be able to hurt your ability to perform well.

5. Why do you want to work here?

The interviewers ask this question because they want to know what drives you to them and how much you want the job. It is tricky because you are being tested on your level of interest for the job. They want a response that they will know that you have taken the time to research company and understand the industry, not just that you are looking for career stability or a solid paycheck.

6. Why do you want to leave your current job?

They ask this because they are looking for patterns or anything negative, especially if you have jumped from job to job in a very short time period. Your answer could raise questions and doubts or even sink your chances entirely. Their ultimate hope is that you are seeking a position that is challenging and has a better fit for your skill set.

7. What are you most proud of in your career?

The interviewers ask this to know what you are most passionate about, or what you feel that you excel at or whether you take pride in your job. Managers would assume that this type of work is what you want to do or focus on in the future. They want to see your ability to articulate well and foster positive vibes to others, as well as your positive energy.

8. Have you ever considered being an entrepreneur?

They are testing you to see if you have the desire to run your own company. The question is tricky because you can unwittingly be lured into talking about that one-time you desire to be your own boss. Your employer might fear that you will go out on your own and compete with their interests. They might consider you as a flight risk.

9. Have you ever stolen a pen from work?

They ask this question in order to get a better sense of your integrity. Here is an appropriate response they are looking for, “Well, I’d be lying to say I haven’t ever absentmindedly 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.”

10. What kind of boss and coworkers have you had the most and least success with, and why?

They ask this question in order to see if you generally have conflicts with people or personality types. It is tricky because you are running a risk of appearing difficult by admitting to unsuccessful interactions with others, unless you are able to keep emotions out of it. They would want to hear good news rather than bad news.

11. If you could work for any company, where would you work?

They would want to know how serious you are about working for them in particular, against other competitions. They are also looking to check the level of your loyalty. You might get caught up in talking because of the casual flow of the discussion and inadvertently leak some well-respected firms. They would want to know that you are interviewing at your first company of choice.

12. How do you define success?

This question is asked to know what ticks you off, but to some, to test your mettle. It is tricky because “success” is highly subjective, and even a perfectly reasonable response can be misinterpreted. A good response is that your answers should relatively be unobjectionable.

13. What career regrets do you have?

What the interviewer is really asking is, “Is there 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 yourself — and others?”. You should give the interviewer a little bit of grit. Also avoiding the word “regret”.

14. Why were you laid off?

They ask this question in order to know how you are going to hold up with pressure and less fortunate circumstances such as job loss. This question is tricky because this question may prompt you to bad-mouth your former employer, and that is a big no no. You should provide a level headed answer that is focused on a business decision by the company to conduct the layoff.

15. What would you do if you won $5 million tomorrow?

The interviewers would want to know if you would still work if you did not need the money. This question is tricky because questions that are out of left field can ambush you and cause you to lose composure. They would want to hear from you that you would want to continue working and that you are passionate in what you do.

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

They ask this question to evaluate your moral compass  by asking how you handled a situation that is delicate that your integrity was put on a test. It is tricky because they would want to know how you manage sensitive matters and are also wary of those who bad-mouth former employees. They would want you to be wise, clear, concise, and professional in your answers.

17. Can you give us a reason why someone may not like working with you?

They would want to know if there are any glaring personality issues in you. This question is tricky because you can easily shoot your own foot with this question. Conversely, you should lead with the positive attitude and go from there.

18. Why have you been out of work for so long?

The implication of this question is that you might not be motivated enough for you to secure a job. It is tricky because the way it is worded is naturally designed to test your resilience. They want to be assured that you possess initiative even when you are unemployed.

19. Tell me about a time you disagreed with a company policy.

This question is asked to determine your ability in making decisions, ease of working with others, and most importantly, whether the candidate will speak up after identifying an area in need of improvement. It is tricky because to say ‘I’ve never disagreed with a company policy’ is tough to believe from even the most amenable employee. You should offer up a real situation that points out a logical and business reason that you were in opposition of a policy.

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

They ask this question in order to know if your priorities are in the right place. Current job first, interview second. The implication for this question is that How is it searching for a job behind your boss’ back?”. It is wise to explain that you always put your job first and schedule your interviews before or after work.

21. What’s a difficult situation that made you turn around? Describe it to us.

They ask this question because it gives them a lot of information in one fell swoop. It is tricky because it is easy to interpret that this is an invitation to brag about your success of your turn around. But don’t fall for it. They would want to see that you are a good problem solver.

22. Are you the type who checks email during your vacation?

They ask this question to make sure that you are smart about taking care of yourself even though you are outside of your office. It is tricky because you  want to frame yourself as someone who is dedicated to work, and at the same time they know that your health and wellness is a key factor to success. They would want to confirm your dedication to getting the tasks that were given to you finished.

23. Is this position a similar role to any other jobs you are considering?

They ask this question to have a better idea of your experiences in the past and your future goals in life. It is tricky because the interviewer might have two goals in mind. You should present yourself as the best fit for the job that you are applying for.

24. What do you think your references will say about you?

They ask this question in order to see if you’re insecure about your references and if you are going to volunteer any negative information about your experiences or in your ability to succeed in your role. You shouldn’t fall for the trap. Be modest, but don’t offer up any negative information. Your references wouldn’t have agreed to be your references if they have nothing good to say about you.

25. Which part of the job sounds most challenging and why?

They ask this question to know if your strengths will align to their greatest needs. The best way to answer this question is to be honest. Also use the answer as an opportunity to present yourself as a candidate that loves a challenge.

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