Most Difficult Interview Questions and How to Answer Them

Difficult interview questions can trip up the brightest of candidates. Recruiters don’t ask you these questions to throw you off your game, but to get a deeper sense of who you are and whether you’re a good fit for the company. 

But to be forewarned is to be forearmed, which is why we have compiled a list of the trickiest interview questions for you and some advice on how to anticipate and answer them. With some advanced preparation, you'll be able to nail interviews and demonstrate the experience that makes you the ideal candidate to be the company's next new employee.

How to answer these difficult interview questions

1.    Tell me something about yourself

This is probably the most asked question during an interview and usually crops up first. It might seem very simple, but because it’s such an open-ended question, it still brings the best candidates to their knees. There are so many ways to answer this question, which is why it is a good idea to think about the reasoning behind it. 

Hiring managers usually ask this question as a way to break the ice and get a little more insight into your personality and determine whether you are a good fit for the company. The best way to approach this question is in a low-key manner, in order to develop a more personal relationship with your interviewer. It is a great idea to start off with your personal hobbies and then build up to a quick rundown of your education, work history, recent career experience and future goals. 

My name is ABC and I have a great passion for music and design. I recently graduated from DEF and during my education, I worked 2 years at XYZ. Here, I have developed the basic tools needed in my profession and I would love to continue working in this job. I would love to use my skills in a fashion industry, as I believe it’s the fastest growing industry with a lot of opportunities. 

2.    Tell me about the worst manager you have ever had

This question seeks to understand your expectations regarding employers and what communication styles you work well with. However, no hiring manager is interested in hearing you bad-mouth your ex-bosses. 

The challenge is here to remain as professional as possible, even though the interviewer will probably ask you to be more specific. You could possibly do this by mentioning which communication style didn’t work as good for you and why. In order to remain positive, you can add that in the end, you have worked well together, but that it was different than with other managers you have had in the past. 

In my past job, my boss had a very different communication style than I am used working with. Although we worked well together and achieved all our goals, it wasn’t the same as other managers I have had.  

3.    How do you cope with repetition?

Don’t be mistaken – most jobs require a lot of repetitive tasks as well. There is a certain amount of repetition in every job, so the hiring manager is trying to find out how well you handle these repetitive tasks. 

In order to answer the question appropriately, you should make sure that you get a grasp of the level of repetition required for the job you're applying for. Here, it’s usually best to show that you are able to handle this level of repetition, by bringing in experiences from past jobs. 

I don’t really mind doing repetitive tasks that are part of the job. In my last job, I had to update and renew our e-mail database for 2 months, but it was necessary for the bigger project I was working on. 

4.    Doesn’t this job seem too junior for you?

When you are applying for a lower-level job than your qualifications might suggest, there is a big chance that you’ll be asked this question during the job interview. This question seeks to find out whether you will be fully invested in your work and not just looking to take it easy. In addition, this question tries to find out whether you’ll be satisfied working there, or whether you’ll leave as soon as you find something else. When responding to this question, try to build a solid case for moving towards a lower-level job in a strategic way. For instance, you might be looking to work fewer hours in the week. The challenge here is to combine your answers with statements where you’ll show your passion for the current position.    

As a manager of XYZ, I was working 60 hours per week, also on the weekends. I would like to work less hours, as I would like to have more time for my children. I am currently seeking for a job that reduces my work load, but I am still prepared to work very hard for great results. 

5.    What are your long-term career goals?

The hiring manager will ask you this question for multiple reasons. This question is designed to find out whether you have a long-term vision or not. In addition, this question is being asked to ascertain if you are planning to stay in the company or if you are planning to leave at the first opportunity.  It might be difficult to answer questions regarding your future, especially if you do not have a long-term goal. It’s best to stay away from an overly specific goal, as the chances are that that specific goal may not be an option at this company. Begin by setting short-term goals. Right now, your goal may be to get a job. But what kind of job? And where do you go from there?   

My past experiences have thought me that my long-term goals are better achieved when I break them up in shorter goals. So, my first goal is to find a position in a growing company. I want to add value in helping this company move forward. My long-term goal depends on where the company goes. I would like to move into a position eventually where I can lead a team. 

6.    Describe a decision you made that was a failure. What happened and why?

Probably one of the hardest questions to be asked during a job interview is the failure question. Negative experiences are difficult to talk about during an interview, because you are trying to present yourself in the best light possible. However, this question is a behavioural question, where the hiring manager is trying to see how you respond in a rather tough situation.  For this question, it doesn’t really matter what type of failure you talk about. The point of this question is to show how you responded to a setback, thought about it and grew from it eventually. Here, it’s more important how you talk about the failure, rather than the circumstance of the failure itself.   

In my first year as a sales executive, I have been in a situation where I had problems addressing complications to my client. In the end, I couldn’t manage my client’s expectations, which is why I lost him. Now, I never let an uncomfortable conversation prevent me from communicating the status of a project transparently. 

7.    What is the worst job you have ever had?

This question is asked to get to know what type of work doesn’t motivate you. In addition, the hiring manager probably wants to find out whether you did anything to fix the problem.  You have to be very careful when answering this question. When you describe the worst job that you’ve ever had, you don’t want to accidentally describe the environment of the company you’re applying for. For that reason, it might also be better to not be too specific when answering this question. And always try to describe what you did to fix the situation.

I once had a job at a theme park where I really had to look for things to do in order to not be bored. I can see why others could strike that job as boring, but I never let that happen to me. I’m a hard worker, so I always looked for things that needed fixing or for things to clean. That is how I managed to always be busy and never get bored. 

8. If you could change anything in your past, what would that be?  

Interviewers often ask this question to examine how you look at your life and accomplishments. The theory here is that the way we think about ourselves usually says a lot about the type of person we will be in the office. Additionally, this question might reveal some juicy responses when the candidate hasn’t prepared to answer it. Try to give the interviewer an easy answer here, so that your response won’t be held against you. It is usually better to answer this question by going into more detail about your educational background, rather than your work history.  In addition, it is always good to mention that in general, all experiences have helped you grow into the person that you are right now.  

If I could change one thing, I would have probably chosen to study Human Resources earlier on during my bachelors. However, my education in Accounting still helps me in my daily work. In general, all experiences in the past have helped me grow into the person that I am today. 

9.    What on your resume is closest to a lie?  

This question is probably being asked to actually detect whether you have been totally honest on your CV. However, if you quickly answer that nothing is a lie on your resume, you might look overly defensive. As if you are actually trying to hide something.  Hiring managers are aware that everyone is trying to present their best side of themselves on their CV. So, the best way of approaching this question is by mentioning that the point of a CV is to show yourself in a good light, however, that you believe that lying and even exaggerating is wrong and then steer the conversation to something positive again.

I believe that to point of a CV is to show yourself in a good light. However, I believe that lying or overexaggerating is wrong, so I personally would not do that. But as you can see on my resume, I have highlighted my achievements at company XYZ to make them more prominent on my CV.  

Final note:

The main reason hiring managers come up with these tough interview questions, is to evaluate your non-verbal communication. This says a lot about how you behave in tough situations and whether you are speaking the truth. Preparing for an interview can therefore be very helpful. These guidelines can help you in your preparation. However, remember that it is also very important to stay truthful and respond honestly.