Tricky interview questions and how to prepare for them

By Indeed Editorial Team

Published 10 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.

It's important to make a good impression in your first interview for a job. Interviewers ask awkward questions that may seem difficult to answer but when you understand the reason for them, you can answer these questions with confidence and inspire the interviewer to consider you a potential employee. There are ways to prepare for those tricky questions that enable you to respond with desirable, appropriate answers. In this article, we look at some of those tricky interview questions, explain why they're asked and provide tips on how to answer them.

Related: Values-based interview questions and sample answers

Why do employers ask tricky interview questions?

You've probably rehearsed your answers to the more traditional questions, which is why recruiters and employers ask cunning interview questions, not to get a right or wrong answer but to evaluate how you respond. Questions might range from hypothetical scenarios to logic puzzles. Whilst these questions may seem irrelevant to the job you're interviewing for, your responses help the interviewer understand your personality, identify skills not listed on your CV, gauge how you process information and how well you function under pressure.

Preparing for your interview gives you a head start on handling these tricky questions calmly and comfortably. Preparation includes researching the company to gain an understanding of what the company does and what its core values are. Review the job description to ensure your qualifications and work experience meet the requirements. You might also want to establish the salary range for similar roles in the industry.

Related: 6 brain teaser interview questions and how to answer them

How to answer tricky interview questions

Below is a list of steps you can take to prepare for and answer questions that might catch you off guard:

1. Prepare for the interview

Consult online resources and review tricky questions prior to your interview. This gives you an idea of the questions that may arise. The interviewer may not ask these exact questions, but this preparation helps.

2. Listen to your interviewer

Listen carefully to the interviewer's questions. Pay attention and wait for the interviewer to finish asking the entire question before responding. This ensures you don't misunderstand the question.

3. Ask questions if necessary

You might ask the interviewer to clarify a complex question to ensure you've understood it properly. You can ask the interviewer to repeat the question if need be. You could also rephrase the question yourself, for instance, Are you asking …?' to ensure your response is appropriate.

4. Explain your thought process

Talking through your thought process to arrive at an answer helps the interviewer gain insight into your critical thinking skills. Explain the maths or logic you used to solve a puzzle. Even if your answer is incorrect, it's the method you used to arrive at the answer that's important.

5. Keep calm

Keep your composure and approach tricky questions with good humour. Don't rush your answer. Nod your head to acknowledge the question and let the interviewer know you're taking a moment to think. Interviewers don't ask tricky questions for no reason. These questions serve a purpose for the interviewer to learn more about you as a person than your CV reveals.

Related: 13 Ways to Calm Interview Nerves

Examples of tricky interview questions

It's hard to prepare when you don't know what to prepare for. The following are examples of questions an interviewer may ask, along with how you can plan your answer:

Have you ever faced an ethical dilemma at work?

This question is a test of your integrity and your ability to analyse and solve problems. It could be a dilemma about reporting an error or betraying a colleague, or offering a loyal client a better deal or making a bigger profit for the company. You could answer something like, 'Ethical issues in the workplace are rarely straightforward. I'd consider all the ways to address the issue and its consequences and, if appropriate, I'd consult with my colleagues before making a decision.'

Have you ever stolen stationery from work?

Since very few people can truthfully answer 'No', an interviewer may be testing you to see how honest you are. If you say that you've never taken so much as a paperclip from work, the interviewer may consider you dishonest. A suitable answer is something like, 'I once had an urgent letter to post to meet a reply cut-off date, so I used a company stamp and posted it during my lunch break. I replaced the stamp the next day because it's against my nature to steal.'

Have you ever considered owning your own business?

While a desire to become an entrepreneur may label you as ambitious, it doesn't endear you to an interviewer. An employer who invests time and money into training you and helping you achieve your career goals expects a return on their investment in the form of loyal service. Be positive. Explain that you're committed to the role for which you're applying and plan to be with the company for a long time.

What task do you dislike doing?

This may seem an innocuous question but it's actually quite tricky. Rather than specify a particular task that you don't enjoy doing, it's a good idea to say that you do what has to be done. You can add that if any task is particularly arduous or unpleasant, you try to complete it right away and get it over and done with.

If you could invite five people for dinner, who might they be and why?

Your answer to this question reveals a lot about your character and how you interact with people from diverse backgrounds with possibly disparate beliefs and opinions. It's a way for the interviewer to discover the people you find interesting and the conversation topics you enjoy. It helps to mention people who are household names, so the interviewer knows who you're talking about. Some examples are:

  • 'Stephen Fry, because he's intelligent and amusing and the dinner table conversation is likely to be lively.'

  • 'Gyles Brandreth, because he's lived such an interesting life, has met some fascinating people and his stories and anecdotes are both informative and amusing.'

  • 'My paternal grandfather, because he died in another country before I was born and I have questions I wish I could have asked him.'

  • 'Ian Smith, ex-prime minister of Rhodesia, now Zimbabwe, so I could ask him if he'd do anything differently if he had to do it all again.'

Related: 8 Common Personality Interview Questions With Sample Answers

If you won the lottery, how do you think you might spend it?

The interviewer is trying to establish, first, if you're more interested in the job itself or the pay cheque and, second, how responsible you are with money. Quitting work to retire in luxury indicates that the job itself isn't a priority for you. Buying a luxury customised vehicle may be considered irresponsible. It's a good idea to say you'd spend your winnings on something like buying your first house, establishing a trust fund for your children's future education or investing in a blue-chip retirement fund.

Can you start tomorrow?

Your answer to this question tells the interviewer whether you're a responsible and loyal employee or not. Unless you're between jobs, if you're ready to start a new job immediately, you're probably prepared to leave your current employer without notice. It's advisable to say that you're obliged to fulfil the terms of your contract by working the required notice period and completing any handover tasks and are available to start the new job after that.

Have you exaggerated anything on your CV?

This is easy. Don't lie or exaggerate on your CV. You can then answer truthfully, 'My CV is an accurate record of my work history, experience and qualifications, as I am sure will be backed up by my references.'

What can I expect your references to tell me?

There is little to concern you about this question. If you suspect that someone might be less than complimentary, it isn't smart to offer them as a reference. Anyone who has agreed to provide a reference is likely to say positive things about you. Simply say that you expect their testimonials to illustrate your work achievements and positive attitude.

If I searched you online, what might I find?

Be honest. The interviewer has probably conducted an online search on your name already. If you've written any articles or blogs that you've published online, you may as well mention one or two. Your social media accounts are generally not for public consumption and some content may be inappropriate in terms of your professional image. It's advisable, prior to submitting your job application, to protect your social media accounts and set privacy levels accordingly.

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