Tricky Interview Questions
and How to Answer Them

See also: Interview Skills

It is not easy being interviewed. Interviewers are likely to ask a job candidate difficult and confusing questions to find out whether they are suitable for the position, not to make them feel silly! If the interviewers are experienced, they know that candidates are likely to have been coached for the interview and can easily answer the more traditional questions.

Experienced interviewers may therefore use trickier questions to gain an understanding of a candidate’s experience, aptitude and skills.

The following ten questions are meant to test you and so it is worth knowing how you might answer them in an interview.

An interview between a young man and woman.

Will you check the emails during your vacations?

The trap: The trap here is that you do not want your interviewer to think that you are not dedicated to the job but, on the other hand, you also do not want them to assume that you will not take enough rest, which can cause problems in your overall performance at the office. Burn-out is a reality, and you need to be aware of it.

The technique of answering: Try to convince your interviewer of your dedication to the job, while also conveying the idea that you are aware of the importance of taking care of your health.

Are you considering any other jobs similar to the position you are applying for here?

The trap: The trap here is obvious:  the interviewer wants to find out whether you are also applying for other roles in other organisations. In addition, the question can also help the interviewer find out if you have previously worked in a similar position.

The technique of answering: The best option is to give a general answer to this sort of question. Do not give a detailed answer by telling the interviewer about all the different positions you have applied for as it might give the wrong idea if your interest and skills are spread all over the place. If you are an author applying for the position of a project manager, do not mention anything about applying for a writing job or your writing career.

an you please say something about your biggest weakness?

The trap: The interviewer wants to find out if you are comfortable in admitting that you have weaknesses, as this awareness is usually deemed the first step to fixing the problem. Another goal of the interview is to learn whether you look forward to making changes and plan to turn any such weaknesses into strengths.

The technique of answering: It is alright if you mention a few of your skills that require polishing. The key point here is that you need to understand that while answering this question, you must not degrade yourself, rather try to focus on telling the interviewer about your plans to make changes.

Where would you like to be employed if you could work for any company?

The trap: It is a difficult question to answer as most of the candidates get confused about whether to keep quiet or mentioned their dream companies. The interviewer here is trying to find out if you are serious about their company or not. Moreover, the interviewer might also need to know if you are applying to other companies or not.

The technique of answering: Imagine you are on a date and your date ask you ‘Who would you date if you could date anyone in this restaurant?’ While answering this type of question, think what you would like to hear if you were to ask the same question of your date. Please answer similarly to your interviewer and try to convince them that the company you are interviewing with is your priority right now.

Tell me some of the reasons you would like to work for our company

The trap: This question is asked by the interviewer to find out whether you have done your research about their company.

The technique of answering: While answering this type of question, make sure that there is a genuine meaning behind it. Do not simply say that you want to work there because the office would provide you with free gym access and has a casual dress code. Work your answer around the company’s mission and core values and how you would like to connect with them.

In five years, where do you see yourself?

The trap: The employers are not interested in candidates who are not serious about their job and are not planning on sticking around. Do not give the interviewer the impression that you might want to change your career path in the future. This may make the employer feel that you will not be committed to the role that you will be appointed to at their company.

The technique of answering: Self-motivation is one of the most important things to consider when answering this type of question. As was stated by the investigators, employers need to find out if you can grow and develop within your field. You do not need to tell them that you see yourself working for them in five years as well, rather discuss the goals that you would like to achieve within the upcoming five years.

The Skills You Need Guide to Getting a Job

Further Reading from Skills You Need

The Skills You Need Guide to Getting a Job

Develop the skills you need to get that job.

This eBook is essential reading for potential job-seekers. Not only does it cover identifying your skills but also the mechanics of applying for a job, writing a CV or resume and attending interviews.


We have tried to offer some tips as to how you might answer these tricky questions in an interview situation. The interviewers are really not trying to trick you, just trying to get beneath the surface of your CV or resume and understand you better as a person and a job candidate.

Do your research and think about how you would answer these, and other possible tricky questions that might be asked, well ahead of the interview. You can look through the questions provided above repeatedly to make sure you are confident that you can answer in the right way. For questions that are not covered here, use the same process and try to break them down into the trap and how you can answer them. Your chances of success at interview depend on how you answer these tricky questions so make sure you are well prepared.

About the Author

Adrian Lomezzo is a freelance writer who loves travelling. He works with different websites as a content manager and teaches students and adults to improve their skills. By becoming a writer, he could travel and yet remain close to everyone, sharing precious information from all corners of the world.