Top 15 Hardest Job Interview Questions and How to Answer Them

Job interviews can be nerve-wracking and facing the hardest job interview questions can leave you feeling unprepared, stressed and disappointed if you fail to deliver good enough answers.

To help you prepare for this, we have compiled a list of the most difficult interview questions that employers ask.

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The Hardest Job Interview Questions

A difficult interview question is a question that is not easy to answer. It can be because of the complexity of the question, or it can be because the interviewer expects a certain answer and we have to do our best to deliver that answer.

You should do your research on the company before you go into any interview. This will help you to know what questions you might be asked and how you should answer them, linking your own skills, knowledge and experience to the job requirements as laid out in the job description.

Not feeling confident before a job interview? Practice answering these questions with a friend or family member and make sure that you are confident in your answers before going into an interview.

What are your biggest strengths?

This question is a great opportunity to sell yourself and make yourself look good.

Do not be afraid to list several strengths when answering, but make sure that you justify each one.

In your preparation for the job interview, you should have learned what the company is looking for in the perfect candidate. Look to detail skills and knowledge that match exactly what the company is looking for.

Consider including the following things for every strength you mention in your answer:

• Why do you consider this a strength?
• How did you develop this into a strength?
• What advantages has this strength brought to your career?
• How have you effectively used this strength in your past work?
• How could you use this strength to your advantage in the role you are interviewing for?

What are your biggest weaknesses?

When people think of the toughest job interview question or the worst job interview question to be asked, this is always top of the list.

It is a tricky question to navigate and many people say it is designed to trap you.

By approaching this question correctly you can demonstrate a strong awareness of your own abilities and flip the question to make yourself look good.

We wouldn’t advise that you provide a long list of things you consider to be weaknesses. You might want to consider just one or two, but give a comprehensive explanation of the choices you have made.

Try to choose things that you have some experience in and would like to develop your skills and knowledge of further. Doing so will enable you to craft a more detailed answer and show an awareness of your own skills and prove that you are committed to developing yourself.

We would advise that you avoid saying skills or knowledge that are essential parts of the job you are interviewing for. For example – do not say you struggle with building relationships if you are interviewing for a sales role.

Consider including the following things for every weakness you mention in your answer:

• Why do you consider this is a weakness? – be gentle on yourself!
• How do you plan on making this weakness into a strength?
• What you have learned from being aware of this weakness and what you do to stop it impacting your performance
• Seek to explain how you feel this weakness will not impact your performance in the job role you are interviewing for

Tell me about yourself

We covered this question in detail in our article How to Describe Yourself in a Job Interview.

This is definitely a question that you can prepare an answer to before your interview and where possible link to the business/industry you are interviewing for.

Interviewers often ask candidates to describe themselves at a start of an interview. It is a good ice-breaker question to get to know more about the person. Delivering a top-quality answer can really help get your interview off to a great start and help you build rapport with the interviewer.

Why are you looking to change jobs?

It is common for people to interview for new job roles when already in employment elsewhere, and there are many reasons for wanting to do so.

Look to explain in your answer the positive reasons for why you are looking to move job roles, rather than focus on the negatives of your current job role.

Talk about these things:

• Promotion prospects
• Learning opportunities
• How the role better suits your lifestyle requirements
• Your interest in the company/industry/type of job
• Other details that attracted you in the job advertisement

Don’t talk about these things:

• Why you dislike your existing job
• Negative relationships with existing colleagues
• Performance related issues you are having

When answering this question you should remain professional and not make negative remarks about your existing employer. However, it is reasonable to discuss things such as progression and learning opportunities that are not available to you that you are seeking to further develop your career.

Why did you leave your last position?

Depending on the reasons for leaving your last job will determine the ease with which you can approach this question.

It is advisable that you be honest and truthful with your answer and give an explanation of what led to you leaving.

Hiring companies want to be confident that the person they hire will stay with them for a long time. Losing staff that recently joined costs a business money in repeating the recruitment process and providing any training.

One of the biggest fears for job hunters is to be judged as a “job hopper”, someone who moves from job to job after only staying for a short period of time.

The modern workplace is different to that of generations gone by and generally hiring managers are appreciative of reasons for why you might have left recent employment after only a short period, but you should be convincing and thorough in your explanations.

Consider these approaches depending on your circumstances:

Made redundant from your last job – sometimes the manner in which we end up without a job is beyond our control and this is one of those occasions. Redundancies can occur as a result of a business’s performance or a change in the economy, factors that are beyond your control. Explain the situation and present yourself as upbeat and positive about your next challenge.

Chose to leave – There are many reasons why you might voluntarily leave a business, however, some hiring managers find your decision rash if not justified as they will fear you could do the same to them. Explain your reasons for leaving and why you felt it was the right thing for you to do. This could be reasons such as progression, working conditions, lifestyle change, your health.

Fired from your last job – This can be one of the most difficult situations to explain but it is better to be truthful. You might choose to explain the circumstances that led to you getting fired and explain your position. If your dismissal was a result of mistakes you made or performance-related reasons, attempt to spin the answer into a positive one by explaining what you learned from this and the steps you are/have taken to ensure it doesn’t happen again.

Can you explain the gaps in your employment history?

This is a question that hiring managers have asked candidates for years, and one that people with gaps on their résumé dread getting asked.

For a lot of people, there will be a simple explanation such as choosing to go travelling or raising children. These are all perfectly reasonable answers, but where your gaps are of considerable length, expand on your answer by explaining how any relevant skills and knowledge that are required for the job role you have kept up to date with.

For example, industries like digital marketing are fast-moving and knowledge acquired from 5-10 years ago will have gaps in it compared to what the modern digital marketer needs to succeed.

If you are returning to work after a long period, take time to refresh your knowledge and skills of your chosen profession or any profession you are looking to go into. In the interview stage, you could be competing with people who are currently working within that profession and have an up to date set of skills and knowledge, giving them a significant advantage over you.

For some, the reason for a gap in their employment history is because they have struggled to secure new work despite actively job hunting. People in this situation may hate admitting this in a job interview as they feel the interviewer will begin to wonder why other employers haven’t hired you before now.

Take the time to explain your job hunting journey and the positive steps you have taken to secure work in the field you are interested in working in.

This could involve taking on unpaid volunteering positions or studying to learn skills that the job requires.

Showing a devoted and positive attitude towards your job hunt will help you be seen as a proactive person who is serious about finding work, rather than someone who is simply waiting for an employer to hand them a job.

How do you react to stressful situations?

If you are asked this in an interview it could suggest that the job you are interviewing for might bring with it some stressful situations. This could come by the way of tight deadlines, challenging targets or dealing with clients.

In this instance, employers are looking for someone who can keep calm in a pressure situation and perform well. However, apart from the current job interview, you are in, it is impossible for an interviewer to gauge how you react under different conditions.

To support your answer to this question it is best to be truthful over how you personally feel you react to stressful situations and bring with you examples of the types of stressful situations you encountered in your past employment.

Bring forward these examples and explain:

• What made them stressful situations
• How you overcame the challenge
• How you handled the increased pressure
• Any particular measures you put in place to reduce the likelihood of it happening again
• What you learned from it

Describe a time you overcame a challenge

This is one of those questions where you should have an answer already prepared in your head that you can unleash with confidence and quality immediately.

Take the time to think of a significant challenge you faced in your career, preferably one from your most recent job if possible. For youngsters with a limited working background, consider a challenge faced in your education.

Once you have thought of one, consider working these points into your detailed answer:

• What the challenge was
• Why it was important to overcome this challenge
• A breakdown of the steps you took to overcome this challenge
• Any relationships you had to form or rely on to achieve success
• What the end result was
• What you learned from this experience and where possible how that can help you in the role you are interviewing for

What would your co-workers say about you?

This isn’t a question you can expect to be asked in every interview, but it is one of those ones that can catch you off guard when asked.

This question provides you with a free ticket to promote what you are like as an employee and as a team member.

Consider talking about these things:

• The positive things your co-workers would say about you
• Why they would say these positive things
• What you do to support colleagues in the workplace
• Any examples of where you have gone above and beyond to support colleagues or contribute to a team project
• What you enjoy about team working and good working environment with colleagues

Where do you see yourself in 5 years?

This question is designed to understand your career ambitions and what you would like to achieve in the job role you are interviewing for. It is a great opportunity to demonstrate ambition but it can also be a trap.

It can be difficult to give a truly accurate answer to this question without knowing a good deal about the company’s organisational structure and promotion opportunities that will be available to you.

The answer you give should reflect your honest intentions of how you would like to progress in your career over time, but not make any wild claims. Saying you want to be the CEO or Vice-President within 5 years when starting from the bottom is highly unlikely and could make you look naive.

In your answer look to cover points such as:

• How open you would be to promotion opportunities
• How open you would be to training and learning opportunities
• Your long term career goals beyond 5 years
• How you intend on achieving your career goals, do you have a career plan?
• What you would like to learn in order to achieve your goals
• Where you see yourself now in your career

Why do you want this job?

This is a direct question and one that can really make or break your interview.

Failing to show enthusiasm around the job, the company or industry could dent your chances of getting hired over other candidates you are competing against.

Try to avoid giving saying that you are only interested in the pay on offer and look to mention points such as these:

• What interests you about this job
• Why you think you would be good at this job
• How this job fits into your overall career plan
• How interested you are in the future opportunties that this job could create
• What you like about the company
• What you like about the industry

You might also choose to mention any additional perks the employer offers, but do not overemphasise the importance of them.

Perks like remote working are great for improving your work-life balance and it is understandable why people would appreciate having that, but discussing a shiny new company car you would get might be best to avoid.

Why do you want to work for this company?

This is a very similar question to “Why do you want this job?”, but it has more of a focus on the company rather than the person interviewing.

To answer this question confidently and convincingly it is important to know as much about the business as possible.

Check out: What Should You Research About a Company Before an Interview

Your answer should refer to your findings and detail what it is you like about the company. Consider discussing:

• What you like about the company
• What you like about the industry they operate in
• The business culture they cultivate
• Are they an organisation that gives back to the community or charities?
• Career development and training opportunities available with this business
• Future promotion prospects
• Is the company a growing business with big ambitions?

Why should we hire you?

The themes to this answer and the previous two questions are very similar and the answers you give will involve the same elements.

If you happen to be asked these questions in an interview, don’t be afraid of repeating your reasons, providing you give justified reasons for the points you make.

When answering this question it is a golden opportunity to promote yourself as the right person for the job and demonstrate any key skills and knowledge that hasn’t yet been discussed.

Consider mentioning these things in your answer:

• The interest and passion you will bring to the job
• Matching your skills and knowledge to the job requirements as defined in the job description
• What extra skills, knowledges and experience you feel you could bring that would benefit them
• Your ambitions to build a career with them (and not leave after six months)
• Why you think you are a good fit for their organisation
• How you think you would fit in with their company culture
• Your past experiences working in similar roles and industries

What are your wage expectations?

This is one of those awkward questions that a lot of people don’t know how to approach. Sure, in our heads we know how much we’d like to be paid, but communicating that can feel awkward for many of us.

Many organisations will not ask you this question as there is already an agreed rate of pay for the job, but experienced job seekers will be familiar with job roles advertised with a salary bracket or with the letters DOE (dependent on experience).

For the type of job roles where the salary is negotiable based on experience, as a job seeker you need to have a good understanding of what someone in that profession and seniority level typically gets paid.

It is not unreasonable to expect a company to know this information too, but having your own knowledge will protect you from receiving a salary offer below the market rate.

When providing your answer be truthful and fair to yourself. Some people might think proposing a lower salary will improve their chances of landing the job, but this isn’t the case. Companies want the right candidate, not the cheapest.

Companies may be willing to negotiate with you and for the right candidate to improve on what they had originally set out to pay.

Just because the answer you give doesn’t match up with what the employer had in mind, doesn’t mean you won’t be successful. However, if the answer you give is far apart from what the employer had in mind, they will be cautious that you could leave their organisation after a short period, in search of the money you want. The best way to combat this is to do your research ahead of time for what is a reasonable salary for this job role.

Check out online salary check services such as Salary.com and PayScale.com.