top 5 tricky job interview questions and how to answer them

25/10/2018 14:23:01

Job interview questions: they can be pleasant - “Tell me about your greatest achievement” - and they can be challenging - “What was your worst experience with an employer?”. However, they’re all designed to test how you think about work and how you respond in difficult circumstances.

There are some particularly common job interview questions that can trip up even the most experienced interviewee - but prepare for them and you could set yourself apart from the other candidates. Here’s our guide on the best ways to answer some of the most asked tricky interview questions:

  • tell me a little bit more about yourself
  • what is your biggest weakness?
  • why do you want to work for this company?
  • tell me about a time you 've failed
  • where do you see yourself in five years?

tell me a little bit more about yourself

This is a common opening interview question. Instead of launching straight into the job interview, your interviewer asks you to introduce yourself. Since this question is so broad, what they’re really asking is “how well do you express yourself?” Though there are many ways to answer this question, we recommend you give a brief overview of your career. Things to include: recent jobs, skills, and certifications.

You can cap off your answer with a little insight into your personal hobbies, but it shouldn’t be the focus of your answer. This is not the time to get too personal. The best way to be prepared for this question? Have a short (1 minute or less) work bio ready. You’ll be amazed at how often it comes in handy. Chances are once you’re finished, something you’ve mentioned will lead to your interviewer’s next question.

So explain what your current position is, briefly discuss your previous experience - making sure to tailor it to your potential employer - and and finish with what you hope to do.

Although it may not initially seem like a difficult job interview question, this is one where you could blow your shot at quickly getting the interviewer’s attention. Mess this one up and it could set the tone for the rest of the meeting.

what is your biggest weakness?

This one can tough because you can’t reveal anything too damaging that will be a deal breaker. In this case, being too honest can be an issue. For instance, saying you’re a procrastinator prone to missing deadlines might not go over too well. Instead, try to think of constructive criticism you’ve received in the past that you’ve successfully addressed. Always make sure to note how you’re working on overcoming the issue.

What’s your biggest weakness is a particular favorite of many interviewers as it allows them to test you. The advice has always been to frame a positive as a negative, which is why the cliche about being a perfectionist exists.

However, hiring managers don’t want to hear that anymore. As with all answers, you should provide the interviewer with a story when you answer what your biggest weakness is. This allows them to put it into context. Explain what you struggle with - whether that’s organization, presenting, whatever it may be - and give a description of a time when it caused a problem. But then make sure you have a solution ready to discuss so you highlight how you’re working to overcome the issue.

The ideal answer here is one that shows you’re self-aware, understand where you struggle in a professional setting, and adds what you’re currently doing to improve on that weakness.

why do you want to work for this company?

This is another of those seemingly innocuous job interview questions, but which could really dent your confidence if you don’t give a strong answer. This is why it’s extremely valuable to expect this one and prepare an answer for it ahead of the interview.

You need to go beyond the obvious - the company has a vacancy you’re qualified for - and really impress the interviewer with your knowledge of their business. You should use this opportunity to show that you've done your homework on the company and how you might fit into the open role. And very important: don't forget to mention why you would match with the company culture!

Explain to the interviewer how your experience and abilities will help their business move forward and attain its goals.

tell me about a time you failed

No one likes to be reminded of occasions when things didn’t go according to plan, but interviewers want to know how you dealt with failure to gain an insight into how you work.

Show “a growth moment". This means you have to explain what you learnt from the failure and how you use what you learnt today. The more you can show that you learned from the mistake, the better you can communicate to the interviewer that, despite this previous failure, you won’t make that same mistake in this job because you understand what went wrong.

where do you see yourself in five years?

This question is asked to determine how the job you’re applying for fits into your long-term career plan. Will you be gone in a few months? Do you have unrealistic expectations of where the role is headed?

To answer this question, like many common job interview questions, stick with honesty. If you hope to move into a more senior or management role, say so, but be realistic. Most interviewers will appreciate your ambition; after all, 5 years is a long time. This can be one of the trickiest job interview questions, since you’re interviewing for the job you want now, not in five years. However, there are clever ways to get around the fact you’re not a psychic.

Hiring managers want to know that you’re setting realistic goals for your career, as well as gauge your ambition and whether or not the role aligns with your goals and your plan for growth. When preparing for the job interview, set out some career objectives and weave them into what the company you’re interviewing at does. If you can describe how your plans for the future fit with the firm’s, you’ll give yourself a great chance at standing out from other candidates.

It’s an opportunity for you to convey your enthusiasm for the position and to explain how you hope to make a significant impact within the organization.



Of course, not every interview question can be prepared for - think “If you were a vegetable, which would you be and why?”. In cases where you’re stumped, it’s okay to tell the hiring manager that it’s a great question and you’ll need a second to think about it. Most interviewers aren’t out to get you so they’ll usually be accommodating enough not to press you.

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