PRO-TIPS: Most Difficult Interview Questions and How to Answer Them


According to a recent study that interviewed 6000 job seekers, over 30% of people felt nervous or even lost their composure during an interview. What’s more, over half said they felt anxious when asked the following questions:

  • “Why should we hire you?”
  • “What is your greatest weakness?”
  • “Tell me about yourself” (see previous article)
  • “What challenges did you face in your last job?”
  • “Where do you see yourself in 5 years?”
  • “Why did you leave your last job?”

Here is what is really behind these questions, and how to answer them:

1. Why Should We Hire You?

What you’re really being asked here is “What can you offer the company?” and “What value will you bring to the role?”.

There are areas to cover when answering this question and the more you cover, the better the chance of securing the job.

Area 1: Match Your Answers to the Job Description

Tailor your answers to align with the skill requirements in the job description as well as relevant qualifications and experience, you should provide one or two real life examples where you’ve applied the skills and aptitude that this job requires.

Area 2: Show Your Uniqueness

Identify qualities or experiences that you can draw you interviewers’ attention to, these could be commercial or cultural events you’ve hosted or participated in, or specific projects you worked. The idea here is to gain extra points by standing out from the crowd.

Area 3: Go Beyond the Job Description

Companies ultimately hire good people to solve their problems and clear obstacles that lie in the way of their success. So - this is a great opportunity to demonstrate that aside from the day to day responsibilities, you’re keen to help the company achieve its goals. To demonstrate this, you can ask “Are there any particular challenges that need to be resolved or efficiencies that can be made?”

Example Answer:

I know you’re looking for someone who can manage a sales team of 15 people. I led the sales team for my previous employer and attained 20% growth, meeting sales targets several times and received “A Best in Class” award for my region. My experience of working with multi-national companies makes me a good fit for this role, as well as my ability to connect with management. Will there be opportunities to improve your current sales processes?

2. What is your great weakness?

At a basic level, interviewers are looking for you demonstrate three main qualities in your answer: self-awareness, honesty and self-improvement.

The traditional advice is to identify a strength that can be portrayed as a weakness, however this is too common and interviewers expect it. Give an answer like that and they’ll think you’re avoiding the question.

Instead, what’s important is that you show you’re open-minded and have a growth-mindset.

Example: My greatest weakness is that I sometimes find it hard to share responsibilities if I’m not convinced the task will be done well enough. It tries my patience when it’s clear something isn’t being done properly. Right now, I’m focusing on learning to trust others more by investing time in their training.

3. What challenges did you face in your last job? And how did you overcome them?

This can be one most the most challenging questions because most people find it difficult to clearly structure their answers. In order to deliver your scenario clearly and concisely to an interviewer you can use the STAR technique, as it will keep your response organized.


As a customer service office, you’re currently handling a complaint.

  • [S]ituation - A client complained that it’s been two weeks and they still haven’t received a response to their enquiry.
  • [T]ask - To find out what went wrong and provide a satisfactory answer to the client.
  • [A]ction - Inform management that a key client has complained and get back to the client within 1 hour. Then investigate the root cause. In this case, there was a typo in the contact information stored for this client. Apologise, provide an appropriate response and offer a discount or goodwill gesture.
  • [R]esponse - The client is satisfied with our response and continues to do business with us.

The STAR technique ensures the examples you give are clearly presented and easily understood by your audience. Remember to start by stating the crisis and then describe how it was resolved.

4. Where do you see yourself in 5 years?

This can be a tough one, but the good news is that you can be honest and still tell your interviewer that you don’t know yet. You should use this as an opportunity to state the broader goals for your career and align them to the prospects of the role you’re applying for. Behind this question, you should be answering:

  • Do you have realistic expectations for your career growth?
  • Are you ambitious?
  • Does this position align with your growth expectations overall?
  • How does this position align with your broader professional goals?

You can point out how this role will help you achieve your career objectives, for example: “I hope to be in a managerial position within five years, as this role will expose me to management and leadership responsibilities across a number of large scale projects”.

5. Why did you leave your last job?

Interviewers are especially interested in knowing why you quit your last job as they’re concerned you might leave their company for similar reasons. As a rule of thumb, you shouldn’t make negative comments about your previous employers, whether you enjoyed your time there or not. Instead, identify some positives about your previous employer that have equipped you for the future, for example “I left my previous job to join a company with more opportunities for professional growth, I’ve learnt a great deal but the focus has been moving operations offshore and I would like a role that offers new challenges and career paths across multiple geographies”.

Team Vanna

Vanna's expert writing team

4 min read

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