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Answering Tricky Interview Questions

There’s no hiding the fact that interviews are nerve-wracking experiences – 93% of candidates have experienced interview anxiety during their career. Most of us feel out of practice by the time it comes to our next job interview. However, by following our golden interview rule of preparation, you will be ready to take it in your stride, even with tricky interview questions.

No matter how much research you do about the organisation, the interviewers, and even your own skill set and competencies, if you don’t prepare for the hard interview questions, these can easily catch you out.

10 Tricky Questions to Takeaway

We have put together a list of 10 common tricky interview questions that you should prepare to avoid being thrown in your next interview.

  1. Why are you leaving your current job?
  2. How do you explain the gap in your CV?
  3. What is your greatest weakness? 
  4. Can you tell me about your worst boss?
  5. Tell me about a time you failed
  6. Why should we hire you?
  7. How do you manage conflict?
  8. Tell us more about yourself
  9. What was the worst job you’ve had?
  10. What’s your elevator pitch?

Keep reading to delve into each of these questions and how you should aim to answer them.

Preparing for Hard Questions

Interviews can be like learning a new language. You prepare what you want to say, say it well and then comes the difficult bit – someone questions what you have just said. If unprepared, the interviewer appears to talk fast and catches you unaware, leaving you unsure of how to answer. 

But, with our interview top tips fresh in your mind, will have prepared well for your interview.

You will have researched the company, the role, and what you would bring to the role and you have some positive examples to demonstrate your skills, show how you manage conflict and how you motivate yourself and others. And, then, from reading this blog, you will have also prepared answers to the tricky interview questions too.

1. Why did you leave your last job? 

There may be very easy explanations, for example, relocation, the end of a fixed-term contract or redundancy. However, your situation may be more complex, with a difficult boss or an unmanageable workload (often a result of the first), there might have been bullying or harassment issues. As far as possible, always try to be positive about leaving your role. Do not be negative about the company or individuals within it. Try and flip your situation into a positive one. Instead, say you are looking to advance your career in the way that the new role would offer. 

2. Why is there a gap in your CV? 

Never feel embarrassed about a gap in your CV. Honesty is the best policy here. If you were bringing up a family or planning for a career break, simply explain this. If you have been able to follow any courses or undertake any voluntary work during this time, you can highlight this here.

It may be that you’ve found yourself between jobs. If this is your circumstance, you can communicate this as giving yourself a few months without work so you can concentrate fully on finding your next role. Stress how you have been searching for a position that provides you with ample possibility to grow and add value.

3. What do you see as your greatest weakness?

When and if this is asked, it is an exercise in demonstrating awareness of where you could become stronger professionally. Do not use it to admit to terrible time-keeping or being a perfectionist. Instead, you want to find an example that you can use to demonstrate your self-awareness of a weakness. But, then you want to use it as a prime opportunity to show how you are actively working on this and putting methods in place to challenge yourself. For example, if you are conscious of not always participating fully in meetings, you can explain how you have set yourself the task of contributing one comment, idea or question when appropriate. Or, if your digital skills need updating, you can demonstrate your self-improvement by signing up for an online course.

4. Tell me about your worst boss. 

Don’t get caught out; you have never had a ‘bad’ boss. Yes, you may have examples of moments of bad management, but never identify the person or the organisation. You may want to highlight an example to demonstrate that you recognise that there is an opportunity for improvement. However, this must be done respectfully. You may wish to word it as the observations of someone early in their management career. You have experienced times when communication has been difficult, or work allocation has been unequal, for example. You can use this question as another opportunity to highlight how you adapted, stepped up or used your initiative. It is never an invitation to moan.

5. When have you failed?

As with questions around weakness, it is important to highlight the learning from the failure and what steps you took to lessen the effects of what went wrong. Did you miscalculate the resources necessary for a project? With any failure, talk about at what stage you realised things were going wrong, and most importantly at what stage did you ask for help and/or put things right. This will demonstrate awareness and honesty.

6. Why should we hire you? 

This is similar to Why should we hire you ahead of the other candidates? Or What value can you add? Prepare for this question by looking again at the job specification and your CV or application form. Talk about the experience and skills you have that are relevant to the role. Give an example, tying together your experience and their needs. If the organisation talks about launching new services, talk about a time when you have contributed to the expansion and that you worked successfully under pressure in these situations. Always relate your experience and achievements to the role in question.

7. How do you cope with or manage conflict?

It is best to have a clear example here and illustrate an appropriate response. Are you the unofficial, but very important, peacemaker in the team, gently sorting the issues that arise in any group? Or have you had to deal with significant conflict directly, ensuring processes were followed correctly and a duty of care was and could be shown?

8. Tell me about yourself. 

Broad questions such as this have their own complexity. There is a temptation to answer too broadly or start too early. Try and stay focused on work examples with one or two added extras; add a bit of you to the answer so the interviewer feels they know you better than when you walked in. However, they don’t need to know your memories of primary school!

9. What was your worst job?

Try to keep this to something very early in your career, and again be discrete about the employer. You can give an example of when you felt your career was blocked, but don’t give an impression of impatience or entitlement to promotion. Or there might have been a time when you were considered the go-to person for unpleasant or even dangerous tasks.

10. Give us your Elevator Pitch.

In other words, tell us in 60 seconds or less why we should hire you.  Preparing for this is positive in many ways. It will help you speak with clarity, helping you focus your own mind on why you want to work for this company and in this role. It also helps you clearly articulate how you, your skills and your experience can add value to their organisation.

Things to Remember

Remember, the interviewer is not trying to make you feel uncomfortable by asking tricky interview questions. They recognise that no one is perfect, but they also need to ensure that the person hired will work successfully in the role, contribute to the team and add value to the organisation going forward. Your preparation and honesty will help them make that decision.

Don’t be afraid to ask for some time. Simply remark that they’ve asked a tough question, and ask for a moment to formulate a response. It’s better to take a deep breath and think through your answer instead of rushing and blurting out something that might not make sense. After all, the interviews are there to gain insight into your thought process. 

If you’d like more guidance to help your interview preparation, check out our resources here. For tailored support with your job search, contact our recruitment experts today.


What are the hardest questions in an interview?

The hardest question in an interview varies depending on the individual being interviewed and the company conducting the interview. However, common challenging questions include those that require critical thinking, and problem-solving, or those that assess the candidate’s ability to handle stress or challenging situations.

What are the 5 unusual interview questions?

The five unusual interview questions examples include:

  • If you could have a dinner party with any historical figures, who would you invite and why?
  • What animal best represents your character, and why?
  • Which fictional character would you like to switch places with, and why?
  • What would your slogan be, if you were a brand?
  • What three items would you have if you were stranded on a deserted island?

What are the toughest behavioural interview questions?

Tough behavioural interview questions aim to evaluate the candidate’s past behaviour, reactions, and problem-solving ability in various situations. Some of the most challenging behavioural interview questions are:

  • Tell me about a time you made a mistake and what you learned from it.
  • Describe a time when you had to deal with a difficult coworker or manager, and how you handled the situation.
  • Tell me about a time when you had to make a tough decision with limited information.
  • Give me an example of a time when you had to solve a complex problem, and how you approached it.
  • Describe a time when you failed to achieve a goal, and what you did to overcome it.

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