27 Tough Interview Questions and Answers: How To Ace Any Interview

This is the ultimate guide to answering tough interview questions!

In this video and blog, Richard McMunn gives you his 27 Top Tough Interview Questions and answers which are designed to help you pass any interview!

Whether you are going for a project management interview, a customer service, interview, a leadership interview, or even a teamworking interview, the questions and answers in this video will help you during your preparation.

List of Tough Interview Questions! 

Below is Richard’s list of TOUGH interview questions that you need to prepare for, if you are to pass any interview. The reason these questions are so tough is because they are designed to make you think, long and hard, about your own experience and situation! Take a pen and start preparing for each and every one of these tough interview questions – the more prepared you are, the better your chances of success.

  1. Tell me about a time when you didn’t get on with a work colleague?
  2. What are you most criticized about at work?
  3. What area did you have to improve on during your last appraisal?
  4. Describe a time when you failed in a work situation?
  5. Describe a time when you changed how you did something following feedback from someone else?
  6. Who’s the worst boss you’ve ever had?
  7. How do you think your co-workers would describe you, both good and bad?
  8. What’s the first thing you would do in this job if you are successful?
  9. What’s your biggest weaknesses?
  10. Describe a time when you failed whilst working as part of a team?
  11. Why do you want to leave your current job?
  12. Why are there some gaps in your employment?
  13. Where do you see yourself in 5 years’ time?
  14. Describe a time when you concentrated for a long period?
  15. Describe a time when you solved a difficult problem?
  16. Tell me about yourself and why you are a match for the job description?
  17. What’s the most challenging thing you have ever done at work?
  18. What is the biggest mistake you have ever made?
  19. Describe a time when you failed to reach a goal you set yourself?
  20. How do you handle stress at work?
  21. Describe a time when you solved a difficult problem whilst at work?
  22. What do you know about our company, our products and services?
  23. Explain a situation where you had to communicate a difficult message to a group of people?
  24. What’s your biggest regret in life?
  25. What’s the last piece of personal development work you undertook?
  26. Describe a time when you dealt with a difficult or frustrated customer?
  27. What did you most dislike about your last job?
In this blog, we'll give you a guide on how to answer tough interview questions

Sample Interview Questions: Colleague Relationships

Q1. Tell me about a time when you didn’t get on with a work colleague?

What not to say:

Don’t say it was their fault and that they were the ones who had the problem, not you.

What to say:

Do say you looked at this as an opportunity to build bridges and resolve the situation with a positive outcome to the benefit of the company.


“In a previous job I can remember a member of staff within the office taking a dislike to me for some reason. He appeared to not involve me during conversations, and when I tried to contribute, he dismissed my views and opinions.”

Whilst it wasn’t a pleasant situation to be in, I knew I had to be the one who resolved it. I started out by trying to speak to him on a one-to-one basis and would sit with him during coffee and lunch breaks. I would always talk to him positively and ask how he was and what he had been getting up to at weekends. He was continually cold towards me, and so I decided to ask him outright whether there was an issue.

As soon as I confronted him on the issue, his attitude changed. Although he didn’t say it directly, I felt he knew he hadn’t been particularly nice towards me. However, since that day we have got on really well and our relationship has progressed to the point that we have met up for a coffee on a couple of occasions outside of work.

This has been beneficial to the team, because we can now work together more productively on important projects. Whenever a negative situation occurs, I will always try my hardest to turn it into a positive one.”

Sample Interview Question: Dealing with Failure

Q2. Describe a time when you failed in a work situation?

What not to say:

Don’t say you are perfect and that you have never failed in a work situation. We all fail at times!

What to say:

Explain how you failed, the impact it had on the team and what you did to put it right.


“When I initially started out in my previous job, I was given an important task by my manager that had a tight deadline. Because I was keen to impress, I started working hard quickly to get the job done and to the right standard.

However, due to my hastiness, I had failed to read one part of the brief correctly, which meant the project wasn’t completed to the right specification. As soon as I realized I had made the mistake, I informed my manager, apologized and looked to put it right.

 I learnt a lot from that experience, and every since then, I ensure I adopt a thorough, analytical approach to all tasks I undertake.

I don’t make mistakes often, but if I do, I will always react positively, take responsibility and learn from the experience.”

Customer Service Interview Questions and Answers

Sample Interview Question: Respect for Authority 

Q3. Who’s the worst boss you’ve ever had?

What not to say:

Don’t say you’ve had lots of bad bosses. This will make the interview panel think it’s you who has the problem!

What to say:

If you have had a negative boss, say you kept your opinions of them to yourself as it’s important you respect their decisions and instructions.


“To be truthful, most of my bosses and managers have been brilliant. There has only ever been one boss where I didn’t agree with the way that he did things, but I was still very much respectful towards him, and I kept my views and opinions to myself.

The only reason why I felt he wasn’t particularly great as a boss, was that he continually changed his mind about how we should tackle certain projects, and he didn’t appear to be confident in his choices.

Having said that, I understood that he must have been under pressure from senior managers, so I always did all I could to help him out and do my own job to the best of my abilities.”

Sample Interview Question: Workplace Reputation 

Q4. How do you think your co-workers would describe you, both good and bad?

What not to say:

Don’t say anything that is a bad match for the job description.

What to say:

  • Do say a number of good things your co-workers would say that are a match for the job description.
  • Say one bad thing and three good things!


“That’s a difficult question, but I guess if I am really honest they would most probably say the one bad thing about me is that I am sometimes not very good at delegating team tasks when we are all working together on an important project. It’s only because I care so much about the finished project that I try to do a lot of the work myself. Having said that, I am learning to let go and trust my work colleagues as they are just as important as I am, within the team.

In respect of the good things, I believe they would say I am reliable and can be trusted to complete a task professionally. I am a loyal and hardworking person and an invaluable asset to the team. And finally, I am someone whom they could rely on in their hour of need, or if they ever needed support in a difficult situation.”

Learn situational interview questions and answers, in our guide.

Sample Interview Question: Your Future Plans

Q5. What’s the first thing you would do in this job if you are successful?

 What not to say:

Don’t say you would sit back and take your time to become accustomed to the role.

What to say:

  • Do say you already have a plan in place of what you intend to do.
  • Break it down into 3 things – learning the role quickly, fitting into the team and making an immediate impact!


“I would want to hit the ground running, and in order to order to achieve that, I would do three things. Firstly, I would learn the job as quickly as possible and in order to achieve that, I would take comprehensive notes and spend time reading up on the role during the evenings, once I got home from work.

Secondly, I would introduce myself to the team and get to know everyone as soon as possible. I feel it’s important that I fit in with the team quickly.

 Finally, I would want to undertake an important project or task to show you what I am capable of doing. Because you would be putting your trust in me, I would be keen to repay that trust by showing you what I am capable of doing within the role, quickly.”

Get access to more tough interview questions and answers via our online course, at: https://www.how2become.com/free-online-interview-training-course/

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