The Most Difficult Interview Questions (and the Answers)
The job interview can sometimes seem more like an interrogation rather than a friendly discussion about your strengths as a candidate.
While you have quite a few common and straightforward questions coming your way, there are a few tough ones too.
Here’s a list of the ten most difficult interview questions and tips on how to answer them.
At the end of the post, you’ll also get to enjoy a few interview tips and tricks to ensure you land that perfect job!
TELL US ABOUT YOURSELF
While the above is not purely a statement, it’s bound to come up in a job interview.
In fact, you’ll probably get it right at the start. It’s the hiring managers way of getting to know you and to understand why you are sitting in front of them.
The best answer
The best answer is short and story-like. You don’t want to keep blabbering on for minutes – five minutes is a good maximum amount of time to spend on this.
Construct the answer in a story-like format; go back to your past and highlight when you became interested in the industry you’re applying for.
You can then highlight your achievements that relate to the job in question. Always build the answer around the qualities of character needed for the role.
“I’m a southern girl who first dabbled in sales at the age of seven when I launched a lemonade stand at the front garden. For the past five years, I’ve been working a sales assistant.
I’d describe myself as a person with a versatile skill set, a strong work ethic and willingness to help customers feel satisfied by the end of the interaction.
Right now, I’m looking to boost my career progress and that’s why I’ve applied for the role of sales executive.
My ambition is really pushing me towards a role where I can help others improve their sales skills and to work directly with customers.”
WHY SHOULD WE HIRE YOU?
This is another extremely common question and one that’s rather difficult to answer. It’s easy to get this wrong and state something obvious like “I’m qualified”.
You need to show your understanding of the requirements of the role and what the company’s vision and values are about. It’s the hiring manager’s way of testing if you know what they want.
The best answer
You definitely want to rely on the elevator pitch answer here. The elevator pitch is a short one to two-minute sales pitch that highlights your personal unique selling point (USP) and your value to the organization.
Focus on your strengths as a candidate, especially in terms of what sets you apart from everyone else.
Make sure you highlight your passion for the industry but also the company you are interviewing with.
“You describe in the job listing that you’re looking for a sales executive with great management skills.
In my 10 years of working in the sales industry, I’ve dealt with teams small and big. I’ve developed strong motivational skills and been rewarded with the manager-of-the-year award for my innovative strategies.
I can push employees to go the extra mile and I will bring these strategies here to push the company further if selected for the role.”
WHAT IS YOUR BIGGEST WEAKNESS?
The interviewer is looking to learn even more about you and to check if you are able to self-reflect.
The modern employer doesn’t want people who can’t take criticism or who aren’t willing to develop, not just in terms of hard skills but also soft skills.
The question is a way of testing if you can examine your actions and behaviors critically.
The best answer
You don’t want to draw too much attention to a big negative trait with your answer. But at the same time, you shouldn’t avoid answering the question.
There is nothing more unprofessional than claiming you have no weaknesses.
In addition, you definitely want to keep the weakness professional – drinking too much is not a quality you want to highlight in a job interview.
Pick a quality that’s more of a frustration and which isn’t required for the job. If you are applying to be a baker, then you might pick something like not being very technology-knowledgeable.
It’s also clever to point out how you are trying to improve this weakness and ensure it isn’t a problem in your worklife.
With the example in mind, you could say you’re now attending an IT course to rectify the situation.
“I sometimes have a habit of spending more time than needed on a task that I could easily delegate to someone else.
While I’ve never missed a deadline, I’m still making an effort to schedule better and to know which tasks I can assign to others.”
WHY ARE YOU LEAVING YOUR CURRENT JOB?
Employers want to understand why people move from one job to another because it can help them identify how long they can expect you to stay.
It’s not cheap to keep recruiting employees and your answer might reveal a problem in your ability to stay put (along with a patchy resume, for example).
The question is to identify your personality, your career objectives and your ambition.
This definitely isn’t a question calling for full honesty – the real reason might actually make the interviewer think twice.
The best answer
Your answer should always show your current employer in a good light, even if you are leaving out of something negative.
You don’t want to talk bad about your previous employers because it doesn’t look professional and it could make the hiring manager doubt your loyalty and commitment as an employee.
A much better way of dealing with the questions is to make the answer focus on your career objectives and ambitions.
Saying you needed a fresh challenge or you’re looking to push upwards in the career ladder is a good idea. It shows ambition and it doesn’t reveal any conflict.
“I’m looking for bigger challenges in my career at the moment and I feel like I didn’t have them at my workplace. I’ve been looking to change the direction of my career slightly and the current employer just doesn’t have opportunities in those areas.”
HOW DO YOU RESPOND TO CRITICISM?
The workplace is not a place where things always go smoothly and everyone just has nice things to say about each other.
With this question, the interviewer is testing if you understand the place of criticism in the workplace and if you are able to learn from it.
It’s not as much about responding to criticism as it is about knowing why people critique others in the first place.
The best answer
A good answer will acknowledge the importance of criticism. You want to let the hiring manager know you understand it is part of life and highlight your ability to take it as a personal development tool. It shows maturity and professionalism.
You should also talk about your coping mechanism in a form of a strategy.
Outline your steps after you encounter criticism and emphasize your focus on learning from mistakes and the feedback.
“I understand criticism is part of life and I always welcome constructive criticism. I can be rather critical of my own work and therefore, I appreciate when I receive feedback from others.
I was recently told to work a draft document for a new client and I felt a little uneasy, as I’m not generally meant to do this as part of my job.
Therefore, I sought advice throughout and actually welcomed critique. Although my manager was happy with the work, I also received a lot of advice on how to improve the document.
I feel the experience taught me a lot about writing but also about being able to overcome your fear and just try new things.”
ARE YOU A TEAM PLAYER?
This might sound like a simple question to answer compared to some of the others on the list.
But it’s actually not a clear-cut ‘yes’ or ‘no’ question.
It tests your knowledge about the role and the kinds of team structures in place in the organization.
The interviewer asks it in order to get your views on leadership and to see if you are able to work in a team or to lead on.
The best answer
You should give a concrete example of a situation where you showed your ability to be a team player, rather than say ‘yes’.
The example doesn’t necessarily have to be from work – it could be something you did as part of your student life, for example.
The important thing is to build your answer around an example and align it with the requirements of the role.
So, if the job you’re applying for is a team project type of role, give an example of how you’ve handled something similar in the past.
On the other hand, if it’s close to an individual role, you want to highlight how you’re able to be your own boss but also step out of this role and help your teammates.
“I believe working in a team is both beneficial and challenging. When I was part of the football club, I learned a lot about communication and problem-solving. You wanted to make things work and come up with compromises because it meant the experience was more enjoyable.
Of course, it was also challenging because people can have different ways of getting their point across and often your own ways of doing things are challenged. But I definitely enjoy both being part of a team and leading one.”
WHO HAS BEEN YOUR BEST AND WORST BOSS?
This is a tricky question to answer because the interviewer is testing two things.
First, they want to know if you understand what makes someone a good or a bad leader.
But they also want to know what kind of person you are to work with – do you run and badmouth your colleagues as soon as you get the opportunity?
The best answer
Just like you shouldn’t badmouth a previous employer when asked about your reasons for leaving, you don’t ever want to name names when it comes to your favorite and least favorite bosses.
A good answer is not about personalities but more about characters. You don’t need to give an actual example of the boss here.
You can just talk about bosses as collective – state how the bosses have been showing specific characteristics. There’s a good video below on what makes a leader good:
Now, when you are talking about the worst boss, don’t mention personal reasons.
Again, you want to talk about leadership qualities and how perhaps some people have lacked those – for example, the bosses have not always been good at communicating the objectives, which you think is important for a good leader.
“I can honestly say I’ve learned from every boss I’ve had. My best bosses have been those who’ve allowed me to take more responsibility as I’ve developed in my jobs. I’ve had others with a more hands-on management style but I feel I’ve flourished under the ones who’ve let me have more responsibility.”
DO YOU HAVE ANY REGRETS?
The interviewer will also want to dig deeper into your past.
Again, the question is about self-reflection and your ability to identify past mistakes.
This can be a question to learn more about yourself but the interviewer might also be checking if you want to clarify gaps or issues in your resume – for example, that you regret travelling around the world even though it taught you a lot of things.
The best answer
You have two options in terms of answering the question.
You could go down the personal route and talk about how you wished you’d spent more times with your nephews or your gran who could have taught you more about life. You could also keep it non-personal and state things like you wish you’d studied harder in high school so that you didn’t have as much catching up in college.
The key is to not just state regret with your answer but to highlight the power of learning from the past.
You want to say that even though you might do things differently now, you’ve still learned from the mistake and used it as an opportunity to become a better worker or person.
“Although I’m overall happy with my life, the one aspect I likely would have changed would have been focusing on this career path earlier.
I’ve really enjoyed working in the field and I wish I had taken more time at university to really focus on my professional development.
However, I feel like my passion is pushing me forward and I’ve quickly gained experience.”
HOW MUCH DO YOU WANT TO BE PAID?
It’s rather likely the interviewer will bring up money and this can be a tricky situation. If you ask too much, you might be excluded from the role and if you ask too little, you might end up with a low salary – the employers always remember!
Talking about money is never easy but it’s important to prepare for this question.
The best answer
You don’t want to throw out a number at this point. The actual salary negotiations should take place later and you might find your answer bite you in the end.
It’s important to conduct research prior to giving your answer – you want to have an idea of the industry standard for that specific role. Consider using a bracket around industry averages.
“Well, according to my research on the industry, the average is between $50k to $80k and I believe my skills and competencies fall along this range. I’m just interested in finding a challenging role that fits my qualifications and I’m confident you can offer a competitive salary.”
TOP TIPS FOR ANSWERING TOUGH INTERVIEW QUESTIONS
The above are the most difficult questions you have to answer during your job interview.
In order to prepare for them and to other job interview questions, here are three golden rules to keep in mind.
Prepare for all sorts of questions
Be prepared for anything. While there are common interview questions most hiring managers ask, each hiring manager, role and company are different. They can have their own interview style and you can get a question you’ve never seen mentioned in any guide – so be prepared.
Research the company well. Understand what the company is looking for by deciphering the job posting and examining the company website for more information. Know the industry and the key trends shaping it.
Understand your own strengths especially in terms of the role. Think about different examples in your life that showcase your suitability for the role.
In order to calm the nerves and to get familiar answering questions, get your friend to interview you. Practicing the interview situation like this can be extremely helpful.
Take your time
When you do hear the question, don’t rush to your answer. Always take a deep breath before you start and compose the start of your answer before you begin talking.
Keep your answer short and sweet and don’t try to talk like a machine gun.
Remember to ask for clarification if you need it. You can even ask the interviewer to repeat the question if you want a bit more time to think your answers.
Don’t fret a bad answer
Now, no matter how much you prepare for the job interview, you never know what might happen. Sometimes your answer just might not come out the way you want and you can feel like you’ve ruined it. Do not panic if this happens.
It’s often possible to return to things you’ve said during the interview right at the end of it.
The interviewer will often give you an opportunity to ask questions or to go over any unclear things – you can use this as an opportunity to return to an answer. For example, you could say something like “I just wanted to go back to when you asked me about my weaknesses. I think…”.
So, when you’ve given an answer and you feel it wasn’t quite as good as you wanted but the interviewer is moving onwards, just breathe. Calm down and focus on the next question – return to the issue later if you feel like it’s still bothering you.
Don’t forget you can also get back to things in the follow-up note you should send after the interview. It’s a great opportunity to get back to anything that took place during the interview and for you to rectify the situation.