The10 Most Difficult Interview Questions (and How to Answer Them) (2024)

Interviews can be stressful and nerve-racking, but the better you prepare, the more confident you’ll feel. Here is VHR’s list of the top 10 most difficult interview questions and how best to approach them under pressure.

1. ‘What do people most criticise about you?’

It can be challenging to best answer weakness-related questions like this one. The key is to be honest and choose a situation which ends on a positive note. ‘No one ever criticises me’ will be considered a poor answer, as this response demonstrates that you do not take criticism well and have a lack of awareness of how others perceive you.

However, interviewees will also want to avoid suggesting that they receive regular criticism during a job interview, so it’s important to find a balance. Refrain from choosing a quality that could be considered to affect your performance in the job you are applying for, and instead prepare to speak about a skill that is unrelated to your ability to excel in your desired role.

2. ‘Why do you want to change jobs?’

Interviewers want to ensure that you are changing jobs for the right reasons, such as better opportunity, more challenges and career growth rather than an undesirable current work situation. The best way to approach this question is to mention how your prospective employer’s company culture is suited to your values, offer how you want to progress in your career or mention an external reason for your decision to move. It is essential that you do not talk badly about your current job – this never reflects well, no matter the justification.

3. ‘What do you do when you know your boss is wrong?’

The third on the list of most difficult interview questions allows the interviewer to decipher how you handle difficult situations and how you see your relationship with your boss. When answering this question, it is advisable to use an example explaining what approach you used when you spoke to your boss about an error, as well as the outcome.

4. ‘Why should we hire you?’

Ultimately, this question aims to find out what you can bring to the role. Read the job description to pick out the qualities which apply to you and prepare specific examples of how you have used these skills in your current and previous roles. Consider your strengths and how these will help you become a top performer in the role and a beneficial asset to the company. Also ensure you mention any experience or qualification that puts you at an advantage in comparison with other applicants and why this would be valuable to the company.

5. ‘What do you like or dislike about your previous job?’

A moderate combination of honesty and respect will help you to best answer the fifth of the most difficult interview questions. Although reflecting on your favourite moments at your previous job are quite straightforward, talking about the aspects which you disliked can be tough. Answering positively shows that you are not holding any grudges and evidences a great attitude and outlook, creating a positive impression in the eyes of the interviewer.

6. ‘Why was there a gap in your employment?’

Despite the difficulties that are often encountered in the current job market and economy, any gaps in employment could be considered negative. With this question, the best approach is to be direct and honest as well as to discuss what you have achieved during this period of unemployment and how this experience will add to your new position. Examples can include volunteering, pursuing certifications and blogging: just ensure you mention the exact skills you used when completing these activities and explain their relevance to the job you are applying for.

7. ‘Where do you see yourself in five years?’

This question aims to find out your ambitions for your career and your future. It is important not to give an over-the-top answer, but also not to undersell yourself or give an unambitious response which suggests a lack of motivation. The best response to the seventh most difficult interview question will demonstrate a desire to grow in the company, progress in your career and enhance your skills and knowledge.

8. ‘How do you handle stress?’

Of course, everyone feels stressed at points during their career, so it is important to think of a few good examples before your interview. Do not mention an occasion that was needlessly stressful, such as prolonged procrastination on your part; a better answer would be a time when you had a difficult assignment to complete within a strict and sudden timeframe. Emphasise how you dealt with the stress well and even how you thrive in stressful situations whilst working, if this is the case.

9. ‘Describe a decision you made that failed. What happened and why?’

Knowing how best to answer failure-based questions can be testing: you want to portray yourself in the best light and discussing your faults is not ideal. Your example response is not the focus of this question, but the way you responded is. Add what you learnt from this experience to illustrate your growth.

10. ‘If you could change anything in your past, what would it be?’

Last on the list of most difficult interview questions, but by no means least, this question allows the interviewer to evaluate your true character and what you think about yourself. Generally, it is more favourable to discuss in detail your educational history rather than go into errors or misjudgements in your work history. Ensure you mention that you have learned from your regrets and that such experiences have allowed you to develop further professionally and personally.

Want more advice on interviews? Here are the 10 Biggest Interview Mistakes. Or, read VHR's Complete Guide To Job Interviews.