Get Your Free Goodie Box here

50 Toughest Job Interview Questions by Richard Borne - HTML preview

PLEASE NOTE: This is an HTML preview only and some elements such as links or page numbers may be incorrect.
Download the book in PDF, ePub, Kindle for a complete version.

The 50 most Difficult Interview Questions you will ever hear and the Expert Model Answers


By Richard Borne Edited by Dave Reynolds

Version 7.0



There is further detailed information on how you can prepare thoroughly for a job interview and succeed where you have previously failed at……..

There is further detailed information on how you can prepare thoroughly for a job interview and a whole new book of more than 200 model answers. Visit the link below:


Also this particular book is free to distribute but note must NOT be altered as it is subject to copyright. So if you found it useful or know of anyone who you think could benefit from it then send them the link below.



Introduction to the 50 most common and hardest interview questions and their model answers
Without further ado let’s look at the 50 most difficult interview questions and their model answers........

In nearly all cases an interviewer will ask similar questions. It doesn't matter whether you are going for a minimum wage job or a senior position in a Fortune 500 company. It is just a question of context although of course the replies will vary.

Interviewing is not just about answering questions. It is about answering questions well and most importantly showing your self in the best possible light. If you find yourself answering with a blunt ‘yes’ or ‘no’ then you need to realise that you are missing an opportunity to sell yourself.

The interviewer is looking to assess your strengths, weaknesses, professionalism and suitability. IF you give closed single word replies then you stand no chance of persuading them to take the risk on you.

Of course if you get asked a question and you don’t have an answer this will harm your application. So we have prepared the top 50 most common and hardest interview questions which you are ever likely to face.

By reading through these you will find that the way you answer a question is one of the keys to a successful interview. An interview is about selling yourself. A skilled interviewer will continually ask ‘open’ questions which by their nature are probing but will allow you to sell your skills and abilities.

Imagine an interview where the replies were all one word answers or short sentences. It would not be very comfortable for either party to sit through and your chances of getting the job would be almost zero.

You need to show you have personality, enthusiasm and a great team ethic to succeed at interviews. There are basically 5 key elements that the interviewer is looking for in a candidate. These are…..

Can you do the job?
Will you do the job?
What is the problem I am here to solve?
Will you take direction and conform to the team ethic?
Will your behaviour represent the department or manager in a professional manner?

All your answers should be modelled with the view that this is what the interviewer is looking to hear.


The toughest questions are the negative ones

So which types of questions will pose the greatest difficulty? When you enter an interview the interviewer expects you to say how brilliant you are and how perfect for the job you will be. They discount this from the start. They therefore pay much greater attention to those questions which raise negative points. Here are some examples

Q. ‘… Have you ever disagreed or argued with your current immediate supervisor?’
Q. ‘….Presumably you want this job because you are disillusioned with your current employer?’
Q. ‘….You seem to lack experience in area ‘x’


Pay particular attention to these types of questions. Interviews will usually be won and lost with these types of questions.

These types of questions need to be answered with as much positive upside as you can possibly muster. The more you dwell on the negatives of your experience and career the poorer the overall impression of your abilities.

An interviewer will usually discount the positive aspects of your answers and look much more closely at the potential negatives in your career.

You should not be afraid to discuss the negative aspects of your career. However a series of positive focused answers will put you in a strong position. It clears a lot of uncertainty in the interviewers mind and importantly reduces their risk in hiring you.

Always answers in the affirmative.

Never answer a question starting with the word ‘No’. There are two reasons for this. Firstly you never want to disagree with the interviewer. Subliminally this will sound like you are disagreeing and to repeat you never want to disagree with the interviewer.

Secondly you want to keep any answers in positive territory. The more negativity that is expressed in an interview the less likely you are to secure the job.

Conversely if the interview is upbeat and positive you will always perform better and be viewed in a favourable light.

The same questions phrased in a different way.
There are always going to be different ways of phrasing the same questions. Do not be intimidated by thinking you need to learn separate answers to dozen of different questions.

Understand the principles behind what is being asked and then concentrate on accentuating the positive and letting your skills and attributes come to the fore.


You will realise that after reading all these questions you need to prepare yourself for the job interview. You need to know and be able to clearly express your job skills are and also your personality skills.

Your job skills and experience should be reasonably static. What I mean by that is that if you have one years experience in a role or skill you cannot suddenly claim to have 5 years experience.

However with the personality traits the answers are totally subjective. The interviewer does not know whether you are enthusiastic, energetic, a team-player or possess 100 other professional behaviours. It is entirely up to you to convince them. You will notice above that only one of the 5 key elements described at the start of this book actually refers to whether you can do the job. The other 4 all relate to personality. That’s a whopping 80%! Use this to your advantage.

The last big element of your preparation is having suitable examples which show real benefits of your actions. If your answers can contain examples with demonstrable benefits then you will sky-rocket your chances of success. It is just a question of making the answer seem real. Every decent interviewer will ask a question and ask for an actual example of just such a situation in your life.

There is further detailed information on how you can prepare thoroughly for a job interview and a whole new book on 200 of the greatest model interview answers at…..

Also this particular book is free to distribute but note must NOT be altered in any way as it is subject to copyright. So if you found it useful or know of anyone who you think could benefit from it then send them the link. It is constantly being improved so the link will give them the latest copy.

I have one final piece of advice regarding job interviews. An interviewer will NEVER hire someone they do not like. If you do nothing else make sure that you have been pleasant, charming, warm and friendly it makes all the difference.

So let's look at the top 50 most common and hardest interview questions and good luck! They are in no particular order just as you may receive them in an interview.

The top 50 most common and hardest job interview questions and their model answers

Q. Where do you see this industry in 5 years time?

A. Although this is the type of question that would be asked in a more senior position everyone should know something about their industry.

The interviewer is not asking for a prediction but looking to see that you understand the current issues facing the industry and what the future trends may be.

Although possible answers are unlimited and will be tailored to each type of business you may find the following suggestions helpful:
- More industry consolidation into larger corporations
- Move away from retail outlets to e-commerce web selling
- More niche players in the market
- Globalisation of the supplier network
- Stronger sales growth in 3rd world countries
- Wider diversity in product ranges
- Increased reliance on software to run the business A more senior managerial position will require you to have an in depth knowledge of the future direction of the industry. This is because your decisions may have a direct impact on the long term direction the company is taking.

If you are going for a more junior position and the question comes up be grateful. By answering with a full and carefully considered reply it will distinguish your application and elevate you above the competition.

What do you know about our company and its product range?

A. This type of question is likely to be more akin to a sales position. This is where you should have done your homework and understood what the company was all about. Failure to have done this could be a major setback!
Make sure you have prepared your answer by researching the company. Of course these days the internet is the best medium for doing this.

What has attracted you to this job?

A. You may find that you only have a limited amount of information on the role. Your understanding of the role may be limited top what you have read in the job description. You may need to reply to the interviewer looking for clarification about some of the aspects of the job.

Concentrate on describing the challenge, rewarding career, and the experience you will gain. Do not mention money if you can help it. Definitely do not say anything negative about your previous employer/boss and wanting to leave. ‘’I just cannot wait to leave my existing employer’’ will not go down well. However the question will not just be role related but will include the wider organisation. Additionally describe what you perceive to be the forward thinking elements of the organisation and what advantages they appear to offer. For example their use of new technology.


Q. Why do you want to change employer and join our organisation and what as an organisation can we offer that is better than your current employer?

A. It is asking for a direct comparison between your current employer and your future employer. An interviewer wants to hear that you are a valued member in your current / previous role. You have worked for an organisation that has trained you to a high level and you have been providing a strong contribution to their skilled workforce. They hope to leverage these skills in their organisation.

A typical answer which deals with such a comparison should read…….

‘My current organisation has been a great career move for me I have learned many new skills eg. x. There is a great team ethic and I feel I have made a strong contribution to their sales team / office / project team etc. However I see your organisation and the role on offer as a new challenge which can leverage my skills and allow me to challenge myself set new goals and further my career in a way that the current organisation perhaps doesn’t offer.’’

Of course this answer needs to be tailored to meet your particular circumstances. Start by listing what you like about your current organisation and the experience you have gained. Compare this with the list of skills and benefits you expect to find in the new organisation. Use this list to tailor your answer.

Stay clear of talking about money. The sub text of this question and so many others like it is the interviewer is asking ‘What’s in it for me?’

You should be replying I am making a contribution and this is how………include examples of how you can make the contribution, which backs up your claims. By saying you want to leverage your skills in the new role and show how you can make a strong contribution is precisely what the interviewer wants to hear.

If you say or even imply the reason for the new job is that you are looking for more money or additional benefits, then this does not imply you are making a contribution to the new organisation. You are in fact saying this is ‘’what is in it for me’’ and does not address the interviewers needs!

What do you dislike about the role being offered?

A. This is an unusual question but reeks of negativity. Keep the answer neutral by saying there is no elements that appear to be of any concern. Then try to keep the reply upbeat by saying you are thrilled to be considered for such an exciting position which is a great opportunity to advance your career.

What have you learnt most from your past career?

A. Another chance to talk about your successes but a truly open ended question. You should talk about your specific skills and experience that you can offer. Remember the skills need to be transferable to the new employer.

A closing statement like the one below will also add value, it will distinguish your answer and elevate your application......‘I have learnt many things as you can imagine. But one point always rings true. Every one needs to be treated with respect, their opinion should be valued and they should be encouraged to contribute to the good of the organisation.’

What would you most like not to do in this role?

A. Dangerous question. The interviewer is probing for things that you didn’t previously like and then they can ask a follow on question about why you didn’t like them. Beware of this trap. Turn the question round and give a ‘model answer’. ….’In an ideal world…..I would like to avoid any bureaucracy or red tape which can delay decisions. Like anyone I am always keen for good progress to be made at all times and everything to run smoothly’. ‘I would like to avoid the situation in the last role where we had tight deadlines and 3 of my staff went off on long term sick with the winter flu last year. Although we achieved our targets it was only through hard effort, team-work and long hours’.

See how these answers portray you in a good light and turn a negative into a positive. Make sure you have prepared an answer otherwise you could see yourself stumbling!


Q. Why personal qualities or attributes will you bring to the role or job and ........Why should I hire you? (is the same question just phrased differently).

A. This is where you need to have a personal pitch of 2 -3 sentences pre-prepared. This needs to relate to the job description. Go through the qualities listed line by line. Then add in the additional personal qualities that you bring to the role.

It is always worth using a qualifying phrase such as ‘colleagues have said of me…I am a great motivator/team builder/technician etc.’. It sounds better if there is a 3rd party endorsement. It doesn’t sound like you are bragging but a colleague is speaking on your behalf.

In addition you will need to have relevant examples which you can offer to expand on. The personal qualities for the role will be attributes such as hard-working, motivating, good communication skills, desire to succeed

You should end your answer with a statement such as ‘ do you think these qualities are what you are looking for from a successful candidate?’. It plants a seed in the mind of the interviewer that they are.

If they reply that they were expecting other qualities then discuss them and offer examples of how you have these and examples of these in action. You need to leave the interviewer in no doubt you have the skills and can demonstrate this with examples.

Have you ever refused to do something at work that you were asked to do?


A. Straight rebuttal. No interviewer wants to hear that you may be a trouble maker?


How long would it take for you to start making a real contribution to the organisation?

A. There is no point in blurting out an answer here because the contribution could be anywhere and you could go off in the wrong direction. Bat the question back to get a more precise idea. ‘’In what particular area of my responsibilities did you have in mind?’’ ‘’Of course there will be a short learning curve while I get up to speed but in the past I have prided myself on being a quick learner who can make an effective contribution in a short space of time. I see this opportunity as no different although I accept it will be a challenge.’’

What is your typical working week in hours?


A. Whatever it takes to get the job done

‘’I like to think I am and effective and efficient worker who gets through a full workload each week. However there are times when I need to work late and weekends and this is fine. This is often due to uneven demands on my time. I will put whatever effort it takes to complete my role.’’

Candidate x has these skills how do you feel your skills match theirs?

A. A ridiculous comparison question. Don’t be drawn on making comparisons with other candidates, it is a golden rule. Stay away from saying anything negative.

However it does raise an important point in the preparation you need to do. Know your strengths but job related and personality related. These should be part of a 3-4 sentence personal summary statement which summarises why you should get the job.

‘I cannot comment on the other candidates and their abilities. All I know is I have these qualities both job related and behavioural (then list them with examples).’

If I said for example another candidate had more experience than you how would you react?

A. A less ridiculous comparison question. However still don’t be drawn on making comparisons. It is important to show your application in the best most positive light not discuss other fictitious candidates

‘There is little to be gained from me trying to compare myself with other candidates.


All I know is I have these qualities both job related and behavioural (then list them with relevant examples).’



Q. I see from your resume that you have never actually been in this role in any of your previous companies. How are you going to manage?
A. Firstly this is an obvious weakness. Weakness means risk to an employer and they are looking for re-assurance that you will adapt to the new environment.

Relate your previous experience to similar situations where you moved departments and had a new role or were faced with new technology which you had to learn quickly. Turn this into a positive about ‘how you are able to adapt to changing circumstances and have a flexible approach. How you pick up new skills quickly. How you enjoy the challenge of the ever changing technology’.

Try to broaden the answer by saying ‘we are all faced with a fast moving and changing environment which constantly presents new challenges. I have always been able to rise to these and perform effectively despite tight deadlines and little support’.

Importantly, then go on to list examples of similar experiences where you have demonstrated such skills. This should close the issue in the interviewers mind and paint a positive picture.

What would you do if you failed to meet your sales target?

A. Don’t be drawn on a specific answer. Sidestep the question. ‘’I will be giving my very best efforts to ensure this scenario never occurs. Throughout my career I have prided myself on my sales achievements to date and see no reason for me failing in the future’’

Are you going to be the best salesman in the company?

A. Another odd question that sometimes gets asked just to see the reaction it causes.
‘‘That is a goal which I will be working very hard to achieve. However I am primary focused on ensuring I exceed my own sales targets, I am not necessarily looking at the success of other salesmen but am sure of my ability to compete with the best salesmen in the company’’

Take the opportunity to talk about your previous successes. It backs up your argument and paints a picture of success.


Are you going to be ambitious to succeed in the role?

A. Over ambition suggest that you will not stay in the role too long before looking to move onwards and upwards. Under ambition suggests you are lacking enthusiasm or drive. 'This is a fantastic opportunity for me. If offered the role I am ambitious to succeed and look forward to performing to the best of my ability with drive and enthusiasm.’


Q. Where do you see yourself in the next 5 or 10 years? A. Answer needs to show ambition but also a commitment to the role on offer. This is a difficult juggling act where a very neutral answer is most appropriate. ‘My first goal is to secure this role and I am ambitious to succeed in it. I am not really looking beyond this. I suppose if pressed I would be looking for career progression like anyone else but 5-10 years is a long time away and I am sure I have many challenges ahead in the current role.

That is a difficult question that would need some thought’. You are unlikely to get pressed further in explaining yourself.


. What do you think the organisation will expect from you in terms of responsibilities?

A. The interviewer is looking for personal skills. Hard work, enthusiasm, professionalism, passion, honesty. Additionally you can express your enthusiasm for the companies products and services and comment on how you see your responsibilities as adding value or increasing sales/profits/turnover. Of course your answer will need to be tailored to the situation.

Close your answer by asking the interviewer if that was what they were expecting or asking what they feel the main responsibilities are apart from those listed on the job description.

You seem to be a bit young for this job.

A. If the interviewer really thought you were too young then they wouldn’t be interviewing you. However they may have concerns even though they think you have something to offer. You will again need to fall back on your personal skills and experience.

Explain what you bring to the role? As for your age politely disagree with the interviewer that although you are younger than other candidates it does not mean you do not have the necessary skills. After all it is up to them to decide.
Turn the question round and say youth is an advantage as you are open to fresh ideas, probably have more energy and ambition and are likely to be more satisfied in the role. On most occasions it is the personality traits such as enthusiasm drive, team work and professionalism that will override experience. Of course a good combination of both is ideal! Play on these traits if your experience is lacking.

You seem to be over qualified for this position. Are you going to find the role a bit demeaning?

A. This is a complement. Your skills are highly regarded and the interview is going particularly well. A good trick is to smile, confirm this is a good thing and ask the interviewer to clarify why they are thinking. This gives you some time to compose yourself and also to set the interviewers concerns in context.
The interviewer will probably say you could get bored, you might not be challenged enough and look to move roles quickly if you get a better offer. This is a concern for you. The way to convince the interviewer is to express your desire to work for the company. The more you have taken the trouble to understand the company its product ranges and shown enthusiasm for joining them the more convincing you will be.

You will want to focus on the challenges the company will offer you and how they will provide a rewarding career for you. This can mark a changing point in the interview. The interviewer is saying that effectively you are an excellent candidate more than capable of doing the job. Your focus now is on convincing them that you see the company as your next major career step.

If you can additionally add that you do have other options for your career and this role is still your first choice then so much the better. It reinforces what you are saying.

You have been working as a temp as so many different places. Why is this?

A. The implication is that you do not fit in or get bored easily. Turn the answer round. Talk about this being a deliberate plan. List the wide range of experiences you have gained working for different companies. They all have different methods of working. Note the fact that you are able to adapt to a new working environment easily and learn new methods of working. You are therefore flexible and adaptable. Back this up by referring to your references from these employers and saying how pleased they were with the work you had performed. This gives you another chance to cement your skills and abilities and all round strong candidacy to the interviewer.

. If you had to pick one quality you had what would be the best one?


A. It is difficult to pick one but it would have to be my honesty or integrity.


What would your job references say about you?

A. Try to make sure that any job references have been sought and written before you go interviewing. This is not always possible.

Where you do have job references then you can say you have references and they are very complimentary around a number of aspects of your work.

It is not a problem if you don’t have references and the question implies that you would probably imagine what they would say.


You may also like...

  • Successful Career Skills
    Successful Career Skills Career by Vivek Singh
    Successful Career Skills
    Successful Career Skills



    Jan 2022

    “You will never change your life until you change something you do daily”, said the popular televangelist Mike Murdock. Once you arrive at the torturous decis...

    Formats: PDF, Epub, Kindle, TXT

  • Virtual Assistant
    Virtual Assistant Career by smita
    Virtual Assistant
    Virtual Assistant



    Jan 2022

    Most people think you can’t generate money from YouTube unless you have thousands of followers, but small companies are paying remote workers to upload their ...

    Formats: PDF, Epub, Kindle, TXT

  • Landing Your Dream Job In 5 Easy Steps
    Landing Your Dream Job In 5 Easy Steps Career by Anita Jelstad
    Landing Your Dream Job In 5 Easy Steps
    Landing Your Dream Job In 5 Easy Steps



    Sep 2021

    DO YOU WANT TO FIND THE DREAM JOB? Wouldn't it be nice to wake up in the morning and actually be looking forward to going to work - at a position where you wo...

    Formats: PDF, Epub, Kindle, TXT

  • 23 Thoughts For A Successful Career Experience
    23 Thoughts For A Successful Career Experience Career by Ryan D. Neely
    23 Thoughts For A Successful Career Experience
    23 Thoughts For A Successful Career Experience



    Jul 2020

    Are you in search of a job? Are you wondering if your education level or lack thereof is sufficient enough to get you hired? Are you having thoughts about wha...

    Formats: PDF, Epub, Kindle, TXT