24 difficult interview questions and how to answer them

Difficult interview questions are becoming more common in recruitment processes in an effort to identify the best talent.

The difficult interview questions they ask you are designed to separate great people from exceptional people.

The difference between the two can be bridged by one thing:


We’re going to show you a large sample of potentially difficult interview questions. These can be worded differently to how we present them. Trust us when we say that there is a right answer to every question they ask, as well as a whole host of wrong ones.

1. Why are you looking to leave your current role?

Why this is a difficult interview question: You can trip up rather easily here by badmouthing your current or former employers. They won’t want to be the next company you have negative things to say about.

  • How to answer it: “My current role, while enjoyable, isn’t providing me with the challenge or progression that I need at this stage of my career. I am keen to remain in a similar role, but I am seeking extra responsibilities and new projects, which I believe this role provides.”
  • How not to answer it: “Myself and management just don’t get along. They seem to have some sort of irrational vendetta against me and seem intent on stripping me of all creative freedom. Given that they don’t know as much as I do, I think they’re being quite rude.”

2. What is your passion/what motivates you?

Why this is a difficult interview question: Employers want to know what makes you get out of bed in the morning. They need to know that the role you have applied for will keep you not just busy, but also engaged.

  • How to answer it: “I’m motivated purely by a desire to push myself as far as I can. I need a role where I can learn and challenge myself. I like to surpass targets and hit deadlines early, as it gives me a sense of achievement at the end of the day.”
  • How not to answer it: “The weekend. And money. I want to make it rain come pay day.”

3. Where do you see yourself in 5 years?

Why this is a difficult interview question: It’s very easy to go too far when answering this question. Be realistic with your expectations, and don’t come across as a threat to other people’s jobs.

  • How to answer it: “I see myself as an invaluable worker who is making a visible impact on the way the company runs and the results it delivers. I can see myself having more responsibility and ownership over projects as well.”
  • How not to answer it: “In your seat” is often a poor choice of answer. While it sounds smart, it can come across as you wanting to put the interviewer’s job under threat. Even worse is “Sitting on a beach earning 20%”, though that could win style points for quoting Die Hard, the ultimate Christmas film. 

4. Describe yourself in three words.

Why this is a difficult interview question: The difficulty here lies with two key factors. The first is that a lack of preparation can leave you at a loss for adjectives. The second is relevance and balance.

  • How to answer it: “Diligent, methodical, reliable. I apply myself well, while maintaining a high standard of method, execution and precision and I can be counted on to meet deadlines and be punctual.” It’s also important here to go through examples of diligence, method and reliability; without these, any three words you pick are just that: words.
  • How not to answer it: “Dedicated, straightforward, fearless.” Chances are you’re none of these. Dedicated is one of those “nothing” words everyone uses. Straightforward tends to mean “say it like it is, brutally, and with little regard for other people’s feelings”. And no, you’re not fearless, you’re afraid of heights.

5. No really, what is your actual key weakness?

Why this is a difficult interview question: You’ll always be asked what your weakness is, and you’ll have prepared an answer which turns a negative into a positive. This iteration of the question forces you to admit where you’re really weak, and what you intend to do to improve and develop.

  • How to answer it: Be honest, but pick your mildest weakness. Even here, justify why you are the way you are by inserting as much positivity as you can into your reasoning.
  • “I’m not super-skilled with Java, and I know that this role gives the successful applicant exposure to that. However, I am an assured hand with C+ and other object-oriented languages, so I’m sure I can get up to the speed required quickly.”
  • How not to answer it: “I’m not comfortable with the idea of not being the smartest person in the room. As a result, if I have knowledge that others don’t have about something, I tend not to share it to retain a sense of power.”

6. Why have you been out of work for so long?

Why this is a difficult interview question: Some employers could be really put off by the idea of someone who is work-rusty. You have to explain that your time out of work wasn’t wasted.

  • How to answer it: “I decided to take a short career break. I wanted to take time out to see more of the world, recharge my batteries and learn new skills. You’ll see that during my time out I gained my PRINCE2 qualification, so you can see that I wasn’t spurning my time.”
  • How not to answer it: “The new Call Of Duty came out. Finding work could wait, but I’ve been looking for work since I completed it.”

7. How do you deal with criticism?

Why this is a difficult interview question: During your career, you will constantly receive criticism, both of the constructive and hurtful variety. You have to show them that criticism is something that you can handle.

  • How to answer it: “Criticism is something I’m always welcome to. I know that some of it can be hurtful, but it’s the best form of advice you can receive. I take every word I receive and turn it into action.”
  • How not to answer it: “Criticism is often negative; I’d rather receive praise for what I do well.”

8. What appeals to you the least about the company/role?

Why this is a difficult interview question: The dreaded opposite of “what appeals to you most about the role”. You applied to this role because you enjoy it, so if there is anything that concerns you, you must turn it into a positive.

  • How to answer it: “There’s nothing that concerns me about the role. If there was, I wouldn’t have applied! The location isn’t as glamorous as other offices I’ve seen, but I don’t plan on spending my time looking out of the window. Your products and the challenges offered by the role are enough to engross me.”
  • How not to answer it: “Helping out with ad hoc office tasks. After all, I’m a skilled developer, not an admin!”

9. How do you prioritise your workload?

Why this is a difficult interview question: Employers want to know what you view as not just your most important tasks, but also what’s important to the company.

  • How to answer it: “I like to take a step back and think of the impact each task has on the project. The tasks with greater end-user importance always move to the top of the list, whilst projects with more distant deadlines hold up the bottom of the list.”
  • How not to answer it: “I like doing the fun stuff first and leaving the boring stuff ‘til last!”

10. How do you deal with conflict and confrontation in the workplace?

Why this is a difficult interview question: Every office seems to have one abrasive, confrontational, overbearing jerk. Prove you’re not that guy.

  • How to answer it: “I try not to get involved in conflict, not even as a peacekeeper. Ultimately, I come into work to do my job to the highest standard possible, and getting into petty fights and arguments with my colleagues isn’t going to help me or the company.”
  • How not to answer it: “Left hook, right hook, uppercut, down. I’m like a young Mike Tyson.”

11. Why should we hire you?

Why this is a difficult interview question: It seems like such an obvious question, but it can be so hard to answer if you’re caught on your heels.

  • How to answer it: While your specific answer will be dependent on your own key selling points (number of languages you can code in, level of experience, approach to problems, etc), they’re really looking to see you sell yourself. Plan this answer to last less than a minute, and pick three of four of your best, most unique qualities to use as your elevator pitch. You need to come across confidently and clearly to sound as memorable as possible. I would also pick at least one, meaty example to back up everything you say.
  • How not to answer it: “I got a B in technical drawing!”

12. Give me an example of a time when you failed.

Why this is a difficult interview question: It’s hard to admit failure, for one, but employers want to see what positives you draw from bad experiences, and how you learn for them.

  • How to answer it: You should follow a structure here. It’s all in your leg… or baby cow… or baby dugong… or caribou… you get the idea.
  • Cause: What did you do which resulted in the failure? Maybe you missed some bugs that were in your code, or you designed a product which didn’t take off.
  • Aftermath: What were the consequences of your decision?
  • Lesson: What did you learn from your failure? What would you do differently? What will you do next time?
  • Fallout: How did you handle any repercussions of your failure?

How not to answer it: Something inane, like “I once ate 14 bowls of cereal and felt like I was going to die”, or something seriously bad, “I once sabotaged a colleague’s project to get ahead.”

13. How do you get a giraffe in a fridge? (obscure questions designed to test your ability to think)

Why this is a difficult interview question: Not only physically impossible to get a normal-sized giraffe into a normal-sized fridge, you’re likely to overthink this question and get the answer totally wrong. This question comes in many different forms.

  • How to answer it: “Open the door, put the giraffe in the fridge, close the door.” If you keep things simple, you will go far. Yes, this answer is totally illogical, but it’s also the right answer. I’d prefer “Build a fridge around the giraffe”, as it shows your ingenuity and craft, but whatever takes your fancy.
  • How not to answer it: “Brute force. Ram it in until it fits - it’s going in that fridge whether it wants to or not.”

14. What achievement are you most proud of?

Why this is a difficult interview question: Justifying why you are proud of it is what makes this hard. They want to see how inspiring you are, and whether you’ve done anything worthwhile with your life up until now.

  • How to answer it: “At university, I always tried to fill my spare time with activities that were going to help me in the long run. As someone who invests a lot of interest in the mobile industry, I have developed a number of different apps. One of them was a little platformer game which took advantage of tilt technology, and it actually got put forward for a UK [app] Design Award. Given my relative age and lack of experience, I was so proud to receive such an accolade.”
  • How not to answer it: “Just passing my degree was an achievement in itself!” is an awful thing to say. “I once assembled an IKEA chair in less than 5 minutes”, while mildly impressive, is completely irrelevant and quite minor.

15. How do you feel about reporting to a younger person?

Why this is a difficult interview question: This is a test of respect. If you’re the sort of person who believes that power comes with age and not those who work hard for it, this can be difficult to answer.

  • How to answer it: “Age is just a number; in fact, young people often bring a refreshing attitude and outlook to senior positions. If they are excellent at what they do then I have no problem reporting to them.”
  • How not to answer it: “I don’t like taking instructions from younger people. It’s a bit like your son telling you to go to your room when you’ve been naughty, it just isn’t right.”

16. What would you expect to achieve in your first 6 months?

Why this is a difficult interview question: This question tests your ability to manage your own expectations. You should neither overestimate nor underestimate what you would want to get done.

  • How to answer it: “I’m not expecting to come in and set the company alight on day one. I realise that it could take anywhere from 6 months to a year before my impact is truly felt. However, I do believe I can come in and impress internally, map out my own ways of doing things and have a total understanding of all the products you develop by then.”
  • How not to answer it: “I want to come in and make an impact from day one. Come six months from now, I’ll be a manager here.” or “Passing my probation period is success enough for me!”

17. What three skills do you have that make you a perfect candidate for this role?

Why this is a difficult interview question: This is about selling yourself as a unique candidate, but also prioritising your skills to match the needs of the company. It’s important to back up everything you say with examples, too.

  • How to answer it: “I would say that I am versatile in the sense that I can program in a variety of different languages full stack. I have proven over time to be highly competent across C+ and Java. I also have the necessary communication skills to effectively communicate with both internal and external clients, as well as members of my team, and my previous experience proves this. Finally, I am a logical thinker; I’m able to take that extra step back and look at problems from as wide a view as I can in order to find the best, most creative solution.”
  • How not to answer it: “I’m a great coder, I’m a hard-worker and I always get to work on time.”

18. Have you ever had to make a tough decision for the benefit of the company?

Why this is a difficult interview question: This is a test of your decision-making metal. In life, you can’t please everyone and you’ll have to make unpopular decisions for the betterment of the company. Those who have backed out of the harder decisions may not be leadership material.

  • How to answer it: “In my view, the toughest decisions affect people. In my last role, I was senior enough to have to make the decision of who to make redundant and who to retain. We were going through a period of instability in the wake of the recession and we couldn’t afford to keep everyone on the books. The decision wasn’t easy, and was emotionally heart-wrenching, but I did my best to help those who I made redundant find work through recommendations and an excellent reference.”
  • How not to answer it: “There was a developer on our team who hated the glare of sunlight in his eyes. I took it upon myself to swap seats with him. It was a tough decision with many consequences, but his quality of life at work has drastically improved.”

19. Do you consider yourself to be a leader?

Why this is a difficult interview question: It’s hard to define yourself as a leader; it’s normally a title bestowed upon you by someone else. In other words, you’re only a great leader if those around you think you are.

  • How to answer it: “I would say that I have many qualities that good leaders possess. As previously discussed, I have it in me to face tough decisions head on, and in my previous positions I was always looked up to for guidance. I always make myself available for people and that really helps keep morale high. My peers would say that I am selfless, which is the most underrated leadership quality one can have.”
  • How not to answer it: “Yes. I’m the loudest voice in the room and I can organise the hell out of a bar crawl.”

20. How would you react if you didn’t get promoted within, say, 3 years?

Why this is a difficult interview question: This question is designed to provoke your real motivations and career aspirations, as well as your patience.

  • How to answer it: “There are reasons for everything. If I didn’t receive a promotion when I felt like I deserved one, the last thing I would do is suspect foul play. I’d take a look at myself, look at the work I have done and focus on the positives. I would request a performance review to see where I am at and to see where I can improve and focus on the future rather than the present.”
  • How not to answer it: “I’d leave. If I feel like I deserve a promotion, I should get one!”

21. How do you measure your success?

Why this is a difficult interview question: People shouldn’t be satisfied with aggressive mediocrity. How achieve and measure a “success”?

  • How to answer it: “First of all, it is important to clarify my definition of success. Success is going above and beyond what is expected of you, and is much more than just making your superiors happy. As a web developer, Google Analytics allows me to measure how well a new site is doing compared to the former version, and surveys and reviews of a positive nature let me gauge the usefulness and effectiveness of site features. Sales figures are also important, and anything that I do to increase profits adds to the successes I have.”
  • How not to answer it: “If my boss is happy, so am I.”

22. Why do you want to work for us over a rival organisation?

Why this is a difficult interview question: Have you done your research? It shows here if you haven’t. You shouldn’t just know the company you are interviewing for, you should also know who their competition is.

  • How to answer it: “Your main rivals are using technology that I would consider outdated and unexciting. I think your technology is innovative and I would relish the chance to work with it. I also enjoy the atmosphere and company culture you have developed and I think that really helps your developers focus and relax.”
  • How not to answer it: “Who are your rivals?”

23. What trends do you predict for our industry?

Why this is a difficult interview question: You need to keep your fingers on the pulse of the industry at all times. You need to come across as someone who has astute observations to make about the industry as a whole.

  • How to answer it: “With the advent of ‘Mobilegeddon’, I think we can expect to see a big shift away from traditional website designs. Soon, all new websites will be designed for mobile devices first before they are designed for the web. Nearly 1/3 of the FTSE100 companies weren’t prepared for the mobile era. The paradigm is shifting, and it will be interesting to see how and if big corporations will adapt to changing consumer needs.”
  • How not to answer it: “There’s going to be more developers and stuff.”

24. Don’t you think you’re a little overqualified for this role?

Why this is a difficult interview question: This isn’t a question designed to condescend you or make you think differently about the role, but it gives you a chance to justify why you want to make a step down.

  • How to answer it: “If I want to get to where I want to be in my career, I need to take one step back before I can take two steps forward. This is a glorious opportunity to progress my career and I’m willing to accept lower pay and lower responsibility to develop the skills necessary to proceed.”
  • How not to answer it: “Of course, but I just really want (NEED) this job.”