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Top 10 Hardest Job Interview Questions and Sample Answers 

What tough questions might you hear from an employer during a job interview? Further in the article, you will find the ten hardest interview questions and examples of answers.

Want to successfully pass the interview and get a job? If you properly prepare for the interview, the vacant position will be yours.

Why Does an Employer Ask Tough Questions in an Interview?

During the job interview, in addition to common questions, the employer can ask the applicant a couple of tricky ones. It is not out of malice. Using this tactic, the interviewer wants to confuse you, and follow your reaction and your train of thought.

All of this will help the employer to make a more accurate picture of ​​the applicant for the position.

The employer is well aware that you most likely were preparing for a job interview, and that all the answers to common questions (like “Tell me about yourself”) have been brought to perfection.

But a tough question will surely make you reflect a little. This will help the employer learn more about your communication skills, and your professional background and understand how you can present yourself in a new job, and what to expect from you.

You need to know that there are no right or wrong answers to tough interview questions. First of all, the interviewer is interested in your reaction to the question, your train of thought, and your point of view.

In the article, you will find the top 10 difficult questions for the applicant that may be asked at the interview and sample answers.

10 Tough Job Interview Questions: Sample Answers and Advices

10 tough job interview questions
Most Difficult Job Interview Questions

1. What other vacancies are you considering?

The purpose of this question is to understand what activities you are considering for yourself. Your response will allow the employer to learn more about your professional experience, ambitions, plans, and career goals.

In addition, the interviewer will be able to understand what professional skills and strengths you have. And then he will conclude whether you are suitable for this position or not.

Advice. Do not list all vacancies and companies to which you have sent your resume.

Yes, at first glance, it may seem that with different skills and abilities, you look like a multi-professional to the employer. But it is not so. First of all, the employer is interested in how you will cope with your work and your job responsibilities, and the fact that you also “know how to cross stitching” does not care much for him.

Therefore, name the employer two or three of the same or related vacancies, and the companies where you sent your resume. It will be quite enough.

Sample Answer to the Tough Interview Question “What Other Vacancies Are You Considering?”

“I am looking for a job in the field of human resource management, so I am not considering any other areas. It is exactly what I am interested in, what I want to do, and what I plan to develop as a professional.

The description of the vacant position in your company, the requirements, and job responsibilities correspond to my professional experience, and skills and coincide with my interests.”

2. One of the Toughest Job Interview Questions Is “What Are Your Weaknesses?”

Purpose. Your weaknesses are not so important to the employer as whether you accept the fact of their existence and whether you are going to change something, develop and work on yourself in the future.

Read more “What Are Your Strengths and Weaknesses: Best Answers to an Interview Question.”

Advice. Try not to delve into the question. Just name one or two of your weaknesses that will not affect the performance of job duties at this place of work.

Steer the conversation to your strengths and highlight your desire to change and become better.

Sample Answer to the Hard Interview Question “What Are Your Weaknesses?”

Weakness: fear of public speaking. 

“To complete a project and prepare a presentation is a mere trifle for me. But when I need to speak in front of colleagues or potential investors, all my confidence evaporates somewhere.

The boss was aware of this problem and usually asked someone from the team to present the project to the public. And one day, while listening to my colleague’s speech, I realized that only I, its author, can present my project, my brainchild in all details, with all nuances.

I began to prepare for the presentation in advance, rehearsed, and even recorded myself on video. These helped me look at myself from the side and notice mistakes – the voice trembled, the intonation was wrong, or there was no eye contact. Now the more I speak in front of an audience, the more confident I become.”

3. Tough Job Interview Question “If You Could Work for Any Company, Which Would You Choose?”

Purpose. By asking the question “If you could work for any company, which would you choose?”, an employer wants to understand how interested you are in getting the vacancy. 

Advice. Do not tell the interviewer the company you dream of working for (and you may have even sent your resume there).

The best thing you can do is to emphasize that the company you are currently interviewing for is a priority for you.

Sample Answer to the Interview Question “If You Could Work for Any Company, Which Would You Choose?”

“While looking for a job, I researched many companies where I theoretically would like to work. But your company has become my number one priority. I support your goals, the mission of the company, and its values. Therefore, I am sure you have a working environment where I can develop as a professional and succeed.”

4. One of the Hardest Interview Questions “Why Do You Want to Work in Our Company (Here)?”

The purpose of the question.

Why is this question so important? Put yourself in the shoes of an employer: would you like to hire an employee who has researched the company, knows its mission, upholds its values, and is willing to work for the benefit of the company, its customers, and consumers?

By asking the question “Why do you want to work in our company?”, the employer wants to make sure that you spend a little of your time and do your “homework”: find and study the basic information about the company.

Advice. The key to the correct answer is right in front of you. All you have to do is turn around the question from “Why do you want to work for the company” to “Why should the company hire me?.

In other words, you need to focus not on what the company can offer you, but on what you can offer the company and why the employer will benefit from hiring you.

Sample Answer to the Tough Job Interview Question “Why Do You Want to Work in Our Company?”

“I have purchased products (used the services) of company X several times and have always been satisfied with the quality. Therefore, I would love to work as part of your team. Moreover, I have five years experience in the manufacturing sector and the necessary knowledge for this…”

5. “Where Do You See Yourself in 5 Years?”

The purpose of the question. The employer wants to make sure that you are planning to stay with the company for a long time. No one wants to invest time and money into training a new employee every six months. 

Furthermore, the employer wants to understand how goal-oriented you are and, of course, make sure that your expectations are realistic.

Advice. You do not need to reassure the employer that you want to work in one place for 10 or 20 years. The main thing is to show him your interest in further development and growth in the chosen field. 

In the answer, you need to demonstrate to the interviewer your understanding of industry trends, as well as your ability to grow and be flexible.

You can describe the skills you would like to develop in the future and the goals you would like to achieve.

Sample Answer to the Job Interview Question “Where Do You See Yourself in 5 Years?”

“In five years I would like to become an expert in my field. I would like to teach and mentor young and emerging designers. I plan to take a refresher course to improve my skills, and also want to gain more experience working with clients.

And, of course, I aspire to work with a team of designers and marketers on large-scale projects.”

6. Tough Job Interview Question “Tell Me About a Time You Had a Conflict Situation at Work”

Purpose. This question allows a potential employer to understand how stress-resistant you are, whether you can easily cope with difficulties, and how you interact with others. Everyone wants to hire the perfect “team player”.

Advice. Convince the employer that you approach resolving the conflict situations professionally: focus on events, not on personalities. 

Your answer to the question about a difficult situation at work built according to the scheme:

Description of the situation – > problem or difficulty – > actions to solve the problem – > result. 

Sample Answer to the Interview Question “Tell Me About a Time You Had a Conflict Situation at Work”

“I managed the creation of a new website which we were supposed to launch in three weeks. (Description of the situation)

One of the programmers found a serious bug in the code and wanted to push back the deadline. But I knew that upper management would be, to put it mildly, dissatisfied. (Problem) 

The programmers insisted on postponing the website launch date. They were categorical and did not want to concede and listen to my arguments. But I realized that the project was extremely important for the company. 

I didn’t want to put too much pressure on the team, so I decided to focus on how I could help them. I convinced them to make a list of tasks that need to be done first. We decided to temporarily postpone everything else and finalize after the launch of the site, albeit not perfectly. (Actions to solve the problem)

As a result, we launched the website on time. It allowed us to increase the number of orders by 15% only in the first week after its launch. Over the next two weeks, our team finalized all the imperfections.” (Result)

7. The Interview Question “Why Did You Quit Your Last Job?”

The purpose of the question “Why did you quit your last job?“. This question lets the interviewer know a lot about you, such as:

  • you quit your last job or you got fired;
  • about the reasons for your dismissal;
  • have a good relationship with your previous employer and colleagues or not.

Your answer will help the employer understand how you can behave in the workplace, what kind of character you have, and what are your values and career goals.

Advice. Give an honest answer that will reflect your specific circumstances, but it must sound positive.

Now is not the time to tell the interviewer what a terrible boss you had and how much you hated your last job.

Sample Answer to the Hard Job Interview Question “Why Did You Quit Your Last Job?”

“To be honest, I was not going to change jobs, but a friend told me about a vacancy. I am interested in the position and, in general, the company. What you offer to your employees sounds intriguing and promising. The vacancy suits me perfectly and matches my work experience and qualifications.” 

8. Tough Interview Question “What Is Your Biggest Regret?”

The purpose. The employer asks this question to learn about your weaknesses and failures and to understand how self-critical and honest you are.

Advice. You can say that you have no regrets. Or, be more forthright and tell your employer about your career blunder.

If you chose the last option, then talk about a setback that will not directly affect or interfere with your ability to do your job.

Sample Answer to the Question “What Is Your Biggest Regret?”

“I regret that at the beginning of my career, I did not know what I wanted to do. But I am sure that my work experience and all the skills I acquired in previous jobs will come in handy for me.”

9. Hard Job Interview Question “What Is Your Greatest Professional Achievement?”

The purpose of the question. The employer wants to know which of your achievements you consider the most important and valuable.

Advice. Talk only about your professional (and never about personal) achievements. And do not be shy.

Sample Answer

“Last year the team I worked for received an award for developing innovative technology to optimize the production process.

My task was to brainstorm with our team and then select the best ideas. Then we tested three projects and implemented the one that gave the maximum result.

The developed technology allowed to reduce the duration of the production process by 20%, which made it possible to double the number of products.”

10. Tough Job Interview Question “What Did You Like Least About Your Last Job?”

The purpose of the question “What did you like least about your last job?” is to find out how high your level of satisfaction from work is, and how demanding and picky you are.

Advice. Never say anything negative about your former boss or colleagues, or about low wages, short vacations, etc. Instead, focus on the circumstance that prevented you from succeeding.

Sample Answer to one of the Toughest Interview Questions “What Did You Like Least About Your Last Job?”

“I liked my job. There have been many interesting projects and tasks during these four years. 

But the problem was that the deadlines for the delivery of projects and the main goals that had to be achieved were constantly changing, without prior warning or discussion.”

Read the post “How to Pass A Job Interview Successfully: 17 Tips.”

Good luck!


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