top 5 tricky interview questions and how to answer them

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 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 questions.

Tell me a little bit about yourself

One of the first things the hiring manager is likely to ask you is to tell them about yourself. This is not the time to get too personal and explain where you grew up and what you like to do on Saturdays, but is the perfect chance to sell yourself while giving them a bit of background.

Although it may not initially seem like a difficult 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.

Career development specialist at MIT Lily Zhang recommends using a formula for this answer. According to Zhang, “one way to structure this answer is to start with your present, go into your past, and finish off with your future”. 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.

What is your biggest weakness?

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.

Sharon Florentine, senior writer for CIO, suggests that “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 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. Monster contributor Carole Martin advises that “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”.

Meanwhile, workplace culture consultant Steve Langerud adds that those who “can move beyond an attractive culture or lifelong dream and put their skills into the context of a deliverable to the employer will move beyond other candidates”. 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.

According to Startup Institute’s Christine Zimmermann, the best answers to this interview question will show the interviewer how you acknowledge failure, show how you reacted and show “a growth moment”.

This means you have to explain what you learnt from the failure and how you use what you learnt today. Glassdoor’s Isabel Thottam adds that “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 can be one of the trickiest 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.

Florentine explains that “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 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 also a chance for interviewers to establish whether you plan to stay the distance with the company, according to Zhang. 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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