Answering 12 Difficult Interview Questions
Career | 13 Dec 2019 | By Guest Author
Answering 12 Difficult Interview Questions

An interview is not an interrogation, but they have something in common: hard and tricky questions designed to find out the truth about you. Even after practice and preparation, some interview questions will still prove to be challenging.

These are 12 of the most difficult questions you will likely encounter in your interviews. This article is not a cheat sheet, but a guideline to help you understand what’s actually being asked and prepare to answer these questions smoothly, confidently - and most importantly - honestly.

1. Tell me about yourself

This simple yet intimidating question is almost guaranteed to be thrown at the start of the interview. Some people make the mistake of rambling about their life story or simply copy-pasting their résumé. So how are you supposed to answer such an open-ended question?

umm nevermind

What the interviewer is actually asking is a summary of you, your education, and experience. Besides that, this loose question is an opportunity to portray yourself and highlight the strengths that you want to show.

Answer this question like telling a short story: go from the big picture down to the specific points. Stay relevant - talk about the vital aspects of your studies and past jobs, hinting at your strengths. Point at your résumé as you progress towards specific examples in your answer.

Don’t let yourself go, though. 1-2 minutes are enough to convey a concise summary of yourself and drop hints that you can expand in other questions later.

2. What tasks do you not like doing?

The interviewer simply wants to know how you work, or the style of working that fits you best and is more likely to make you more productive. If the question is asking for a negative (like this one), always remember to add a positive side yourself.

Some people like routine activities over spontaneity. You can say, “I’m not a fan of ad-hoc assignments since it disturbs the schedule I organized, but I’m getting used to it.” This way, you’re telling them both the style that works and doesn’t work for you, so the interviewer can have an idea of the ideal work situation for you.

You can also add that despite you don’t like a certain task, you don’t mind doing it if needed. This shows that you don’t mind going outside the comfort zone.

Just make sure you don’t complain about tasks essential to the job. It doesn’t help if you say you hate maths in an accounting job interview.

3. What are your weaknesses?

DO NOT say you’re a perfectionist. That’s a meaningless cliché and doesn’t add anything to your answer.

This is one of the harder question to answer since you have to be honest but also not shoot yourself down. The smart thing to do is to mention a common weakness not essential to the job, and of course add a positive aspect to your answer.

Superman and kryptonite.

Is it kryptonite?

For example, if you get lazy when there’s work to bring home (which means your scored high in Lifestyle in Dreamtalent’s Working Style quiz), you can say that you’re less effective if there’s work to bring home. Then you can add that to prevent this, you tend to finish everything before you go home. This is just an example on how you can spin your weakness into a strength.

If you really are a perfectionist, then say it in a different way. You can say that you tend to collect too much information before starting a task, or something like that.

4. What is the harshest criticism you’ve ever received?

Another version is asking about the criticism you receive most often. Both questions are similar to asking about your weakness, but this one expects more from your answer: how you deal with criticism, and what you’re doing to improve yourself.

It may be difficult to recite a stinging criticism in front of interviewers, so take a breather and stay calm. Being able to accept (constructive) criticism objectively and openly is one thing interviewers look for.

As always, don’t forget to turn this negative question with a positive answer. You can mention your (positive) reaction to such criticism, and the steps you’ve taken to address the issue and your efforts in improving yourself.

5. What is your greatest achievement?

This question can measure you on many levels. Obviously, the first purpose is to see your ability and accomplishments. Interviewers can also learn about your work ethic - what you consider “great”, and your personality, such as tendency to take credit - mainly the Modesty metric in your Dreamtalent results.

You can answer this question with a little storytelling. Start by defining the background situation, what you did, and the results of your contributions that make it a great achievement. Make sure it’s recent (not from 20 years ago). Pretty straightforward, right?

But what if we don’t have an achievement, especially for the fresh grads among us with little to no experience? It’s no problem. An achievement doesn’t have to entail formal awards and recognition, and there are many humble things that can be considered great. It doesn’t even have to be career-related.

Rocky Balboa on the Rocky Steps from Rocky (1976).

Getting straight A’s is ordinary, but doing that while juggling side jobs shows that you’re hard working and good with time management. Running a department is nothing special, but leading a team while raising twins and studying for exams is an achievement.

6. Describe a difficult situation at work that you went through

What they actually want to know is how you made it through the challenges. While this question be used to measure what you consider “difficult”, interviewers are less interested in the details of the challenges itself and more to the solution you presented.

Your answer should be focused on results. After briefly explaining the background of the problem, make sure you put more details into the process of your solution and finish strong with solid results. It’s even better if you present numbers or testimonies from co-workers, supervisors, or clients.

Don’t go overboard in complaining about the situation itself, finding faults in others, etcetera. Remember, these questions are hard because they measure more than one thing, and this one can tell interviewers if you’d rather work towards a solution or shift the blame.

7. How well do you handle pressure?

This question may hint that the job you’re interviewing for may bring a lot of pressure, so interviewers are particularly interested if you can take the heat. And of course, the ideal answer should be that you can handle pressure well.

To prove this, you can give an example or scenario from your experience where things were tight and busy. Then, describe your thought process and the steps you take to keep your cool and deliver under pressure. However, saying that you put your headphones on and ignore everyone is not showing that you can handle pressure.

If you feel that you’re struggling with pressure, as many others do, just be honest with your answer. As always, be sure to end with a positive note. For example, you can say that since you’re not comfortable with overwhelming tasks, you tend to finish things before the last minute and don’t shy away from asking for help.

8. How many golf balls can you fit inside this room?

Trick question! This one is actually designed to see how you handle pressure from an unexpected challenge, just like the question before. Both you and the interviewers won’t know the answer, but they’re more interested in your thought and logic process than golf balls.

Stay calm. Show them that you can handle pressure coolly without panicking. It doesn’t matter how many balls you think can fit, but still try to give a proper estimate. After all, this question is one where the process matters more than the answer itself.

9. How do you handle conflict with people?

Translation: am I going to enjoy working with you? This question aims to find out your style in working with other people, such as being a team player, dealing with disagreements, and if you’re going to be a pleasant co-worker or a difficult member of the team.

If you’re interviewing for jobs like Human Capital, customer service, or sales, this question can double as a skill assessment since conflict resolution and empathy are essential abilities in those people-centric jobs.

In the end, a good answer ideally shows the balance between respecting others and the ability to make the best decision. As always, it’s always helpful to provide an example from your experience.

10. What about this 3 month gap in your resume?

Have you been doing anything worthwhile in your time between jobs? It’s understandable that you may have difficulties getting a new job or if you decided to take some time to breathe. If there are any extenuating circumstances, such as medical or family matters, just be honest about it.

If you made good use of your time, you won’t feel like this.

Otherwise, what interviewers want to hear is how you made the most out of your free time. Are you staying productive by taking classes, doing side jobs, or learning the ropes of a small business? Filling your resume gap with experience is a good sign of your productivity.

11. Why should we hire you?

This question usually appears nearing the end of the interview. What can you offer that other candidates can’t? Why should the company bother spending time and resources in hiring you?

This is where you summarize your strengths, your potential, and other load - experiences, skills, and such. You would want to tailor your answer to be more practical and refer to the requirements and challenges presented in the job description, and how you can contribute to those.

Show your confidence and enthusiasm. Lift yourself up, but don’t shoot others down. This question is a big chance to deliver a strong finish to your interview and make the recruiters more confident that hiring you is a good decision.

12. If payroll got mixed up and employees received incorrect amounts of compensation, what would you do?

A scenario question like this one will measure your ability to think fast and your actual capability for the job itself, in this case for a payroll position. Make sure you did a thorough research of the job description and practiced beforehand, and you’ll be fine.


This guideline is meant to accompany the preparations for interviews that you can see in the part 1 and part 2 of the articles. These questions may be difficult, but once you learn what’s actually being asked, and with enough preparation, you can turn them into your advantage. Good luck!