38 challenging interview questions (with sample answers)

By Indeed Editorial Team

Published 12 July 2022

The Indeed Editorial Team comprises a diverse and talented team of writers, researchers and subject matter experts equipped with Indeed's data and insights to deliver useful tips to help guide your career journey.

Interviews are an opportunity for employers to assess your skills by asking you various questions, some of which can be difficult to answer. In addition to standard questions about experience and skills, employers increasingly ask challenging questions to test your lateral thinking while under pressure. Learning about difficult interview questions can help you to prepare responses to them, which can increase your confidence in your next interview. In this article, we look at 38 challenging interview questions, including general, experience-based and in-depth questions, alongside some sample answers.

10 general challenging interview questions

Below are 10 examples of general challenging interview questions:

  1. How well do you respond to criticism?

  2. What did you dislike about your last job?

  3. What are your weaknesses?

  4. Why should we employ you?

  5. Why do you want to leave your current job?

  6. Tell us a little bit about yourself.'

  7. What are your main weaknesses?

  8. Tell me about your strengths.

  9. What do you know about this company?

  10. What makes you stand out from other candidates?

Related: 31 common interview questions and answers

10 experience-based difficult interview questions

Below, you can find 10 examples of experience-based difficult interview questions:

  1. Give an example of a time when you showed initiative.

  2. Describe a time when you failed and how you dealt with it.

  3. What unique skills can you bring to this organisation?

  4. Give an example of a time when you experienced difficulties with a colleague and how you resolved it.

  5. How would you describe your work style?

  6. Tell me about a time when you had to make a challenging moral decision.

  7. Give an example of when you solved a problem.

  8. Tell me about a time when you disagreed with your supervisor or manager.

  9. Tell me about a time when you worked in a team.

  10. Provide an example of when you used critical thinking.

Related: How to develop effective interview questions: a guide

10 in-depth difficult interview questions

Here are 10 examples of in-depth difficult interview questions:

  1. Tell us what your ideal job looks like.

  2. How do you gain clients' trust?

  3. How do you maintain your motivation when working on repetitive or challenging tasks?

  4. Describe what you think success looks like.

  5. What resources do you consider necessary to fulfil this role?

  6. How long do you think it will take for you to make an impact at this company?

  7. If you were to start your career from scratch, what would you do differently?

  8. Do you think your career has been a success so far?

  9. Tell me about your long-term professional goals.

  10. Tell me what you think is the hardest part of working in a management position.

Related: 8 common personality interview questions with sample answers

8 difficult interview questions with sample answers

Here are eight difficult interview questions, along with an explanation of how to answer them and some sample answers:

1. List five unconventional uses for a paper clip

Interviewers ask this question to gauge your creative abilities. Due to this, the more unorthodox uses you can come up with, the better your response is likely to be. A potential employer may ask this question to see if you can help their organisation by developing innovative solutions to complex problems.

Answer: 'I think that you can potentially use a paper clip as a nail cleaner, jewellery clasp, mini screwdriver, hairclip and compass.'

Related: Why creativity skills are important and how to develop them

2. What is your spirit animal and why?

There's no right or wrong answer to this question. Here, the interviewer is more interested in how you explain your choice. Try to answer this question in a way that provides some insight into your personality, rather than offering a cliched response, as this can help an interviewer to determine whether you'd be a good fit with their organisation.

Answer: 'My spirit animal would be a monkey. The reason for this is that monkeys are nimble and intelligent. They also work well as part of a team and are great problem-solvers.'

Related: Interview question: ‘Tell me about yourself'

3. What are some things you believe in that the majority of other people don't?

This question allows you to demonstrate how you see the world differently from others. Good answers to this question typically demonstrate that you have your own views and that you're not afraid to express them. Moreover, a successful answer would normally relate these views with skills that are essential for the role for which you're interviewing. For instance, if you're interviewing for a role that requires strong customer service and problem-solving skills, you'd aim to link your views with these abilities.

Answer: 'Unlike many, I believe that we're all naturally compassionate and altruistic. That's why I always try to understand the details of why a customer may be unhappy and work with them to find a solution. Once I can empathise with a customer, I find that they're much more amenable to a resolution.'

Related: How to answer the interview question 'how would you describe yourself?'

4. What would you do if you won £10 million?

Interviewers ask this question to determine how motivated the candidate is by money. With this in mind, try to answer honestly while also demonstrating your enthusiasm, motivation and positive traits. When answering, it also helps to outline some of your key characteristics in your response.

Answer: 'The first thing I'd do is pay off any debts I have and donate some of the money to a cause I feel passionate about. I'd also use this as an opportunity to travel widely, as I believe this enriches your understanding of the world and different cultures. Additionally, I'd continue to work as it gives me a sense of fulfilment and purpose.'

5. If stranded on a desert island, what two items would you want and why?

This is a great icebreaker question that allows you to show what you prioritise and can provide the interviewer with insight into your decision-making abilities. When answering, try to provide a balance of practical and entertaining items. By doing this, you can demonstrate that you're resourceful while also providing an insight into your personality.

Answer: 'In this scenario, I'd take a laptop and a solar-generated charger with me. Beforehand, I'd download journals and other useful resources that would help with life on the island. I'd also have access to games, music, pictures and other items I've downloaded to ensure that my resilience stayed as strong as possible.'

6. If you were one of our products, which one would you be?

Here, employers are looking to see how well you know their company. When answering, ensure you provide detailed examples of their products, including their key features and benefits. To prepare for this question, thoroughly research the company before the interview and make a note of some of the organisation's products and why you like them.

Answer: 'While your proofreading app is one I use the most, if I had to choose just one product that aligns with who I am, it'd be your keyword analytics tool. The reason for this is that I enjoy researching topics and finding related keywords and phrases to create the most relevant and interesting content that I can. It's fascinating to me as it's like doing detective work to uncover the most desirable results. Alongside this, it can provide an interesting insight into the target market's search intent.'

Related: 10 common telephone interview questions (with example answers)

7. What qualities do you admire most about yourself?

Interviewers ask this question to assess your confidence levels. A good answer clearly outlines what you consider to be your positive qualities, while also relating these to the role's core requirements. When answering, remember to give examples as to how these qualities help you achieve workplace goals.

Answer: 'I admire the level of dedication I give to completing tasks. In the past, I've had a leading role in complex projects that required a lot of research, which I knew I had to complete to find the right solution for the project. This dedication paid off when I completed the task and I received positive feedback from the clients.'

Related: Smart answers to interview questions (with examples)

8. What is your idea of an amazing day?

Everyone has different ideas on what makes a day amazing. Here, you can demonstrate your positive attributes while also showing the interviewer that you're dedicated to your career. In your answer, ensure that you clearly outline what motivates you and how you stay focused and positive.

Answer: 'For me, an amazing day starts with a morning run to clear my head. After getting ready for work, I then start catching up on the latest industry trends and news to motivate myself for the day ahead. I enjoy meeting with clients to share updates, implement new ideas and answer questions, so an amazing day at work would involve one where I can also connect with others.'

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