10 difficult interview questions to be aware of

Man on pink background scratching his head looking confused


Most of us have found ourselves completely stumped by an interview question at some point – and it’s an uncomfortable feeling. Being prepared for difficult interview questions is an important part of preparing. We highlight 10 of the trickiest questions, why they are asked and how to answer them.

1. Why do recruiters ask difficult interview questions?

Interviews can be quite formulaic, as there are lots of standard questions and standard ways to answer them. For the recruiter, it can sometimes be challenging to get a real sense of the person they are talking to.

Asking difficult interview questions is a way to see more of an interviewee’s true character, their thought processes and how they respond to challenges. So when you’re asked a tricky question, see it as an opportunity to demonstrate why you would be a good addition to the team.

It’s less about catching you out, and more about giving you a chance to shine. Here are 10 tricky interview questions to be ready for.

1. What’s your greatest achievement?

This is not so much a difficult question as one that needs a little time for reflection. By the age of 50 you will have had many achievements, and it can feel overwhelming to have to mentally sift through your entire career history in a few seconds.

Interviewers often ask about past achievements and things you are proud of, so have a couple of examples up your sleeve.

2. Why are you leaving your current job?

This isn’t specifically a tricky question, but sometimes the reason you’re leaving might not be something you want to mention. Problems with a colleague or workplace stress are common reasons to leave, but you might not want to share that level of detail.

This is a frequent question, so have a straightforward answer ready, for example: “I enjoyed the role but I had been there for x years and feet it was time for a new challenge.”

3. How would you describe your working style?

If this isn’t something you’ve been asked before it can be hard to answer. Typical working styles are idea-oriented, detail-oriented, supportive or logical. These styles tend to align to the type of work you do.

4. What does success mean to you?

This question is more about understanding you as a person and what motivates you. Be honest, but do consider what the interview might infer about you from your answer. Instead of a flippant answer like ‘a Lamborghini’ – take the opportunity to tell a story about a success at work, how it made you feel and how you celebrated it.

5. What is your biggest weakness?

It feels uncomfortable to highlight something negative about yourself in an interview, but again this question is about understanding you as a person. It’s assessing your honesty and self-awareness. Share something that you would like to improve about yourself and any steps you’re taking to address it.

An example might be that you don’t take enough time for yourself in a working week, but you are now making an effort to take a 20 minute walk at lunchtime every day.

6. Can you tell me about your most challenging time at work?

This is an opportunity to talk about a challenge and – importantly – how you overcame it. Again, it’s straightforward as long as you have prepared an example to talk through.

7. What are your least favourite tasks in your role?

There are always tasks that you are less keen on at work, but the key here again is to demonstrate initiative or problem-solving. Have you found a better or faster way to complete the less appealing jobs you need to do?

8. How well do you respond to criticism?

A good response to this question is to say that you don’t take things as criticism – it’s feedback. If someone has taken the time to point out something that needs work, that’s helpful information that will make you better at your job.

9. Tell me about a time you disagreed with a company policy?

The aim here is to find out how you handle conflict. What the interviewer is looking for is for you to explain a situation where you had to take action to address a policy or decision that wasn’t working for you, a client or a colleague.

10. If you were a chocolate bar, which brand would you be?

This is just one example of a nonsensical style of interview question – once popular in ‘cool’ tech companies and advertising agencies. These questions are designed to put you out of your comfort zone and see how you react. The answer you give is not really important, it’s all about how you justify it. An example of a response to the chocolate bar question is to name a brand because ‘I’m full of energy and will help you get through a bad day.’

With any interview, preparation is key, so always give yourself time to think about how you might answer key questions and what you want to highlight about your skills, experience and personality.

Take a look at our article on common interview questions, our guide on how to prepare for a video interview, and further information on interview skills.

Comments [1]

  • Laura says:

    The one that always gets me, and I know it shouldn’t, is the old chestnut “Tell Me About Yourself”. I find I fumble for a sensible answer, going on about jobs in the long distant past as I have many years experience. I just can’t get my head round this one at all, and how best to tackle it.

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