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The 20 toughest interview questions

Back view of female job applicant make good first impression at work interview in office, millennial woman candidate talk, impress HR managers or recruiters at hiring. Employment concept
Interview questions can range from the bizarre to the complex. Photo: Getty

The 20 toughest questions and challenges that have been posed in interviews by UK companies has been revealed.

Job site Glassdoor analysed hundreds of thousands of interview reviews left on the site to create the list, which ranges from the bizarre to the complex. All the questions come from recent interviews with UK companies, including Asda, Airbnb, Ovo Energy, and Morgan Stanley.

Jo Cresswell, careers expert at Glassdoor, offers advice on how to answer some of the toughest interview questions:

What one thing would you take to the moon?

This bizarre question was asked to a candidate interviewing for a job at supermarket giant Asda.


Cresswell says: “Depending on the role you’re going for, you need to consider what you want to convey in your answer. Do you want to come across as practical, sentimental or something else? For practical answers, consider items such as moon boots, an oxygen mask/tank or first aid kit for survival. For sentimental answers, consider items such as your favourite book, photo of your loved ones or a diary to capture your experience.

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“You’ll want to have an item in mind and a reason as to why you’d take it to the moon. Make it relevant to the role you’re interviewing for, but ensure you remain authentic to yourself.”

If you had £50,000 to start up a new company where would you put the money and why?

This tricky question was asked at a graduate interview at financial services company Admiral Group.

Cresswell says: “First up, prepare yourself with an idea of what new company you would want to start; what industry and what problem you’d be looking to solve or value you’d be looking to add.

“Demonstrate your business acumen by acknowledging the priority areas in which investment needs to be made when starting a business. You might want to consider overheads such as office space, equipment such as computers, costs of any product development or marketing requirements.

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“This doesn’t need to be a complete scientific answer, but you will need to demonstrate an adequate level of business awareness and be prepared to respond to any follow-up questions.

“This could be a good way to demonstrate your values — for example, would your company’s mission be related to a social or environmental cause that you feel passionate about? Would your new enterprise be designed to help a certain segment of the population? How does it relate to your current career path?”

How do your friends describe you?

This thought-provoking question was posed at an interview with online fashion retailer ASOS.

“Try to avoid cliched, one word answers such as ‘helpful’, ‘trustworthy’, ‘reliable’,” Cresswell says. While these may all be true, you can guarantee that every other candidate will be saying the same thing.

“Instead, paint a picture of a few different scenarios which demonstrate how your friends see you. For example, the time you were able to support your friend with their business plan due to your strong knowledge of a certain business issue. Or when one of your friends was struggling with a personal problem, and turned to you as she sees you as honest and dependable. These short stories will make you far more memorable to a recruiter and allow your personality to shine.

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“Maybe you could consider actually asking your friends and colleagues what they think of you before commencing an interview process, so you are basing this response on real world examples?”

The top 20 toughest interview questions:

The Bizarre

  1. Tell us two truths and a lie.

  2. If you could have a superpower, what would it be and why?

  3. What one thing would you take to the moon?

  4. Should you choose to jump from an aeroplane or climb a mountain? Explain why?

  5. If you won £10m, what would you do with it?

The Complex

  1. If you had £50,000 to start up a new company where would you put the money and why?

  2. How many windows do you think there are in London?

  3. How many taxis are there in Oxford? Derive your answer mathematically, not anecdotally.

  4. Is a Jaffa Cake a cake or a biscuit?

  5. Estimate the annual revenue of an outdoor swimming pool.

The Thought-Provoking

  1. What do you consider a challenge for the world and what do you do to solve it?

  2. Name a minimum of 15 qualities that define a great leadership.

  3. What makes you happy?

  4. If you were inventing a product based on a fruit, what would it be and how would you market it?

  5. How do your friends describe you?

The Physical

  1. Build a bridge on a table using straws and cardboard in a team.

  2. Solve a Rubik’s cube.

  3. Can you make a tower using marshmallows and spaghetti to hold one of these cans?

  4. Play a ping-pong game app.

  5. Design a car park.

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