8 Tough Interview Questions and How You Can Answer Them

By Indeed Editorial Team

Updated 3 November 2022

Published 2 August 2021

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.

While certain interview questions are conventional and predictable, others may catch you off guard. It's critical to plan as much as possible for unanticipated situations. Challenging interview questions vary greatly by industry, but there are a few tough questions that employers frequently use to discover more about you as a candidate. In this article, we discuss why hiring managers ask tough interview questions, explore some frequently asked questions and assess what they're looking for in your answer with some examples to help you prepare your own.

Related: How To Prepare for an Interview

Why do hiring managers ask tough interview questions?

Hiring managers ask tough interview questions for various reasons. One objective is to understand you better. While delivering a concise, compelling description of yourself may be challenging, being able to do so provides a background for employers and makes it easier for them to understand you. Hiring managers may also ask challenging interview questions to assess your degree of experience and familiarity with demanding tasks. This is more frequent in technical positions like engineering, computer programming, or accountancy. To prepare for these kinds of questions, ask friends or coworkers in your field for samples of test questions they've received.

Lastly, hiring managers can ask difficult interview questions to learn more about your cognitive thought processes. For instance, they may ask you an unusual and abstract question like, "If you were a flower, what kind of flower would you be?" The hiring manager is not seeking a specific solution here. Rather, they're assessing whether you can think quickly and substantiate your response with logical reasoning.

Read more: Common Interview Questions and Answers

Common difficult interview questions with sample answers

To prepare for difficult interview questions, it can help to explore some typical questions with tips for how to answer them and examples of strong answers to use as a guide. These questions can vary based on your industry, but there are some common questions you may come across in any interview, such as:

1. What sort of critical feedback do you most frequently receive?

This is akin to asking, "What is your greatest weakness?" Employers ask this question to see if you're self-aware and actively working on self-improvement. To effectively answer this question, consider a genuine piece of criticism you've received or a flaw you're conscious of. Give a concise explanation of the criticism and a description of the legitimate steps you've taken to improve yourself.

Example: "I've been informed in the past that I often speak over other people in meetings. While I'm enthusiastic and passionate about the projects I'm committing to and love working with others, I also recognise the importance of active listening and acknowledging the different ideas offered in the room. I've made it a point to actively listen by taking notes. I've also tried to be the last one to contribute while others are speaking."

Read more: How To Assess Yourself (With Self-Evaluation Examples)

2. Tell me about a moment when you conquered a challenge

Employers ask this question to learn how you react to adversity. When addressing behavioural and situational interview questions like these, you can apply the STAR technique. The STAR technique is a systematic approach to answer a behavioural interview question by specifying and detailing the particular situation, task, action, and result of the scenario you're describing. Give a concise explanation of the scenario, your part in it, the action you took to remedy the problem, and how the problem was resolved as a consequence.

Example: "I worked as a retail manager at a department store during graduation season. A client bought a dress online and had it brought to the store, where it was mistakenly bought by another customer. Before contacting the original buyer, I discovered the same dress at a different store nearby. I had it brought to her house the morning before her graduation, along with a gift card to thank her for her undying support."

3. How do you handle stress?

Hiring managers want to be reassured that you may be able to manage stress productively and positively to preserve a conducive corporate culture. You can answer by describing your normal response and providing a descriptive example to substantiate it. To respond to this question, try to focus on your positive actions and not your negative thoughts.

Example: "In tough situations, communication is imperative for me, even if over-communicating is required to ensure that my entire team is on the same page. In my previous job, I was working on a big project with another department when I discovered duplicate work was being performed. We pushed the project ahead and ended up contributing by arranging a weekly meeting and maintaining clear communication and honest feedback with our teams."

Related: What Are Resilience Skills? And How to Improve Them

4. Can you tell me about your best and worst management experiences?

Hiring managers may ask you this question to understand what you like and dislike about different management styles. Your response may assist them in assessing whether you would be an ideal fit for their organisation's particular management style. Respond to this question as truthfully and respectfully as possible.

Example: "One of my previous employers, while extremely brilliant, had a tendency to strictly supervise the work of my team with limited freedom in how things were conducted. It undermined my self-confidence, and I felt like there wasn't much potential for personal growth and improvement. Fortunately, my most recent manager was excellent at listening to my needs and assisting me in obtaining the resources I required to attain my objectives. I thrive in environments where management fosters collaboration."

Related: 10 Employability Skills You Can Develop (With Definition)

5. Why did you leave your previous position?

Hiring managers can greatly benefit from understanding this information. It helps them determine if the position may be a better fit, whether they can offer you what your previous company lacked or whether you may have had a role in contributing to an unpleasant work experience for you and your previous employer. Answer this question truthfully, but avoid going into too much personal or unpleasant information.

Example: "While I appreciated my experience at my former firm, there are no longer many advancement opportunities that match my professional aspiration. I believe that this role at your company is an excellent fit for my skill set and career goals."

Related: How to Explain Your Reasons for Leaving a Job

6. Why do you want to work here?

Employers frequently ask this question to ensure that you've thoroughly considered and researched your decision to work for their company. The hiring manager would like to see how your skills suit the position, why you're passionate about the position, and how you may fit into the corporate culture. This inquiry is especially pertinent if you're moving sectors or job positions.

Example: "When I started looking for a new job, I deliberately searched out organisations that value ethics, sustainability, and innovation, and your company is at the forefront of the list. Your company has always been forward-thinking in using technology to improve customer experience, and I'm searching for a position where I can put my love for excellent UX to work."

Read more: A Guide to Singapore Work Culture

7. Why should we hire you?

Employers may ask this question to learn what sets you apart from other candidates they may be interviewing. Explain how your experience, talents, and characteristics make you the greatest match for the job in your response. Make sure you thoroughly read the job description ahead of time to understand what traits they're searching for.

Example: "I am a great fit for the role because of my passion for organisation and demonstrated talents in workplace efficiency. In my prior position as an administrative assistant, I devised a strategy for reorganising the office supplies cupboard by category. We placed fewer purchases and saved 30% on office supplies in the next year because products were easier to discover. I'm thrilled to apply my abilities to this position."

Related: Interview Question: 'Why Should We Hire You?'

8. Do you have any regrets?

Hiring managers may ask this question to get a self-evaluation of your potential flaws and shortcomings. To respond to this question, you may reply that you have no regrets in life for a specific reason. Make it a point to tell them that while you have made errors, you have learned from them in order to become a better person. If not, you may choose a regret or a fault that you were still able to overcome in some way.

Example: "I often wish I had known what I wanted to achieve much earlier in my career. Having additional years to grow and improve would allow me to be a better employee. However, in my former job, I gained abilities that I would not have learned otherwise and that benefit me in my current position."

Read more: 20 Common HR Interview Questions and How To Answer Them

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