How to Answer the 20 Hardest Interview Questions

Reviewed by Melina Theodorou

Illustration of a woman and a man sitting across each other seeming confused

Interviewing is a far cry from a walk in the park; with nerves flying all over the place, and the struggle of maintaining the correct body language, it’s difficult to focus on the important part of the interview; the questions. Aside from the most common interview questions, employers ask their candidates more tricky ones to see if there are any inconsistencies.

Although this can be nail-bitingly terrifying, there’s no need to panic; we’ve listed the hardest questions with suggestions on how to tackle them below, to help you prepare for your interview and bag your dream job

Check out an interview example below:

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

The trap: How you answer this one will tell the interviewer a lot about your character and attitude. It may also be an indirect way of asking about mistakes, failures, and regrets.

How to answer: You could choose something that you wanted to improve on but never got the chance to, or an educational experience you missed; saying something like ‘The one thing that I would change if I could go back in time, would be attending university. Although being thrown into full-time work at a young age allowed me to develop a great work ethic and vital skills such as teamwork and how to use my initiative. I sometimes regret not living like other teenagers and learning useful skills through an educational course.’ 

2. ‘If you die, what do you want to be written on your tombstone?’

The trap: Although this question is completely bizarre, it’s used to figure out what a candidate wants their business legacy to be.

How to answer: The idea here is to say something that shows your business accruements. You could say something simple like ‘I’d want to be known as an iconic leader’. You could also take a gamble with this hard interview question and say something funny like ‘Out for lunch, be back later” to show your humorous side.

3. ‘Everyone has one exaggeration on their job application. What’s yours?’

The trap: The employer is trying to catch out the dishonest candidates. Hopefully, your application is free from any mistruths, and you will sail through this question.

How to answer: You know that you’ve been honest on your CV so make sure this comes across in your answer. You could say that you are confident that your CV accurately represents your experience and work and that ‘they are welcome to reach out to the references provided if you’d like them to vouch for your attributes.’

4. ‘How would you describe yourself in one word?’

The trap: Employers ask this question to figure out what type of person you are, and what your confidence level is, they also try to gauge if you will be a good culture fit. 

How to answer: You have to tread carefully when answering this question and make sure you tailor your response to the job description. If you’re going for a role as a designer or art director ‘creative’ would be a good description, for example.

5. ‘How do you define success?’

The trap: This question gives hiring managers an insight into your priorities; they want to see if you’re motivated by paycheques, challenges or learning new skills. 

How to answer: It’s important to be specific and give a job-related answer to this question. You could say something like ‘Applying my knowledge and skills on building your portfolio through XYZ marketing campaign and seeing the businesses success grow.’

6. ‘What would you do if you won $5 million tomorrow?’

The trap: The point of this question is to judge your work ethic and see if you would still work if you didn’t need the money.

How to answer: Even if you would want to leave work and jet-set around the world – do not tell your potential employer that! They want to hear that you would continue working because you’re passionate about what you do. Showing that you’d be irresponsible with your money is bound to raise a red flag.

7. ‘Have you ever been asked to compromise your integrity by your supervisor or colleague? Tell us about it.’

The trap: This tough question is designed to evaluate your moral compass by asking how you handled a delicate situation and put your integrity to the test. They also want to see how you handle confidential information. 

How to answer: It’s vital that you choose your words carefully when answering this question. Make sure you don’t reveal any sensitive information about your previous employers (if you spill the beans on them, then you’ll be likely to do the same with this company). You could say something like ‘There was an incident where a supervisor had asked me to partake in a project that seemed unethical, I wasn’t happy taking part on something that went against mine and the company’s morals as I was very dedicated to our success.’

8. ‘Tell me about a time you had to deliver some bad news.’

The trap: Hiring managers are looking to see if you have the correct social skills. Dealing with sensitive information like this means you need to be fair and compassionate. 

How to answer: The key here is to describe how you will plan and rehearse your delivery. It’s important to show compassion and be tactful when delivering bad news. If you had to fire someone or give them a warning, use this as an example.

9. ‘What would you do if you found out your best friend at work was stealing?’

The trap: The point of this awful question is to test your loyalty to your friend and company.

How to answer: Before you answer, ask what the severity of the theft is. Then explain that if it’s something silly like a pen, you’ll remain loyal to your friend but advise them to return it as it is company property after all. If it’s something more serious, you’ll have no choice but to turn them in as they are putting your job at risk too.


10. ‘How did you make time for this interview? Where does your boss think you are right now?’

The trap: Hiring managers want to know if your priorities are in the right place. They want to see if you’re truthful to your current employer, so they know how you will act with them if you decide to search for a job after they hire you.

How to answer: Never tell them that you’ve taken a ‘sick day’ (even if you have). Be vague with your answer and say something like ‘I am using my personal time for this interview; my boss doesn’t ask for further details. He/she is most interested in my results.’

11. ‘Are you the type of person who checks email during your vacation?’

The trap: This is a tricky one. You want to show that you are dedicated to the job yet, understand the importance of work-life balance and can arrange your time to succeed at work and time where you can switch off and relax, too.

How to answer: You could explain that you’re extremely dedicated to going above and beyond, but understand that it’s important to relax and not work on personal time off. You could say ‘Before I leave for a vacation, I always make sure all my duties are covered before signing off, and I do make sure my supervisor has my personal phone number should an emergency arise.”

12. ‘Will you try to take my job?’

The trap: Your potential employer wants to see how ambitious you are, but whether you are the kind of character to throw someone under the bus to get there too (and let me tell you, nobody likes that kind of colleague).

How to answer: You could say something like ‘Maybe in about twenty years, but by then, I suspect you’ll be running the entire company and will need a good, loyal lieutenant to help you manage this department.’

13. ‘What didn’t you like about your last job?’

The trap: Regardless of how much you hated your last job, this isn’t a counselling session where you can ramble on about all the reasons why you were desperate to move on. This question is designed to highlight your weaknesses and eliminate whiney employees.

How to answer: A perfect answer would be: ‘I did not feel my responsibilities were challenging enough or that there were opportunities for professional advancement’. This just shows your passion and dedication to progress – which is never a bad thing.

14. ‘Tell me one thing you would change about your last job.’

The trap: Similar to the above, this is to see where your strengths lie. If it was something that was in your power to change, it would go against you. Take a minute and think of a wise reply.

How to answer: Don’t overshare or make derogatory comments to your former manager. You must show that you can vocalise your opinion when a problem arises. You could say something like ‘I would change the system we were working on as I believe if it was faster, we would have all been a lot more productive.’

15. ‘Tell me about a time you disagreed with company policy.’

The trap: Employers want to see from past experience how you would behave at their company and whether you would be disruptive.

How to answer: It’s no good saying ‘Nothing.’ as it indicates that you’re a bit of a push-over and won’t stick up for what you believe in. On the other hand, the reason for your disagreement needs to be valid. Use a logical reason to describe why you disagreed with the policy and provide feasible solutions, too. You should also mention the steps you took to address this policy or at least the attempts you made. 

16. ‘How do you respond to stress and pressure?’

The trap: Hiring managers ask this question to see if you crumble or thrive under pressure.

How to answer: ‘I don’t generally tend to feel stressed since I follow an organised plan to ensure that my work is delivered on time. That said, if something goes against schedule, I will focus on finding a solution rather than stressing out about it.’ 

17. ‘Do you have any regrets?’

The trap: Employers might ask this question to see if you’ve had any shortfalls in your life. Tread carefully when answering to ensure that it doesn’t hinder your chances of success. 

How to answer: My only professional regret is that I didn’t discover what I truly wanted to do until I was 25 years old. Although I learnt transferable skills in my previous roles, I would have benefited by having more time working in this industry. 

18. ‘Why weren’t you promoted during your time at the last company you worked for?’

The trap: Hiring managers want to see how ambitious you are and whether you’d like to develop your career with their company. 

How to answer: ‘The company was going through financial struggles during my time there, and I was one of the few that wasn’t made redundant. However, I didn’t feel it was right for me to approach the topic of a promotion when I knew that the company couldn’t afford it.’ 

19. ‘How many hours a week do you usually work?’

The trap: Some employers ask this question to identify if you manage your hours effectively, while others want to see that you’d be dedicated and put in extra work if needed. 

How to answer: ‘I’m committed to my job and would work extra hours to help out the team if needed – that said I praise myself on completing my tasks to a high standard during my regular working hours.’ 

20. ‘What are a couple of the most courageous actions or unpopular stands that you have ever taken?’

The trap: Employers ask this question to see if you can stick up for yourself or something that you believe in. 

How to answer: ‘I overheard someone making a discriminatory remark towards another colleague, so I went over to their desk and asked them to stop and apologise; otherwise I would go directly to HR and report their actions. While it did take courage to stand up to them, it was the right thing to do.’ 

Have you ever been asked any of these questions in an interview? How did you answer them? Let us know in the comments section below!

This article is an updated version of an earlier article originally published on 10 November 2017.