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Tough Interview Questions You Need To Know How To Answer

Suzie Finch
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The best jobs don’t come easy, competition can be high and Interviews can be tough, we mean really tough. Listen up people, you need to be on your A Game!

Interviewers aren’t just asking you difficult questions for the sake of it, they want to be satisfied that you can demonstrate the skills listed on your CV, can fulfil the ambitions and expectations of the role and how you react to pressurised situations.

When answering interview questions (especially the tough ones) take your time, consider the questions asked, stay calm and give measured answers. More often than not interviews are not half as bad as you imagine them to be.

So here it goes, the tough interview questions you need to know how to answer...

How do you handle criticism?

Whether you are a seasoned pro or just starting out, everyone needs pointing in the right direction from time to time and will be criticised in the job they do at some point. Positive feedback is great (if delivered in the right way), nobody likes to feel they are being told off. How you are given the criticism is what makes the difference here.

POSSIBLE ANSWER: “At some point we all need guidance and pointers, this feedback is what helps us improve and develop in our positions. In-fact I actively welcome the opportunity to listen to colleagues and take on board any constructive criticism that helps me improve.”.

What motivates you?

Obviously we’re all driven by financial rewards, great benefits and short commutes, but DON’T mention these (it will hurt your chances), employers are looking for more constructive answers. Answering this question is bespoke to you, however our suggestion below would work well for a client services candidate.

POSSIBLE ANSWER: “I’m passionate about customer service and helping clients obtain the best possible experience. Nothing makes me more satisfied than building strong client relationships which contribute towards business growth.”.

Alternatively, perhaps Richard Branson is what motivates you? …

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Are you a team player?

Employers love a smooth sailing ship, teamwork is a crucial factor in creating this. A properly functioning team all pulling together will create a happy, productive and efficient workplace, this is the dream scenario for employers and employees alike. Don’t be the lone wolf, let the employer know you can play well with others.

POSSIBLE ANSWER: “I really enjoy being part of a team, sharing projects and achieving goals, it provides a real sense of comradeship. This said, I can work equally as well on my own and can be trusted to deliver on time and under pressure.”.

How would your current boss describe you?

This could be a difficult one depending on the circumstances you left your last employer. Steer clear of any negativity (however untrue this might be - yes we’re endorsing a little white lie here if necessary) and remember your current boss must have thought highly of you in the first place otherwise they wouldn’t have hired you!

Pull out all the positives you can and keep things professional…

POSSIBLE ANSWER: “My last boss would describe me as reliable, conscientious and organised who was willing to go above and beyond to get things done. During my tenure I achieved a high level of work satisfaction exceeding agreed KPIs. I worked independently most of the time with little supervision.”.

Under employment law it’s not possible for past employers to give you a bad reference, therefore play this interview question safe and by the book.

How do you feel about taking direction from your superiors?

Employers want to know how you’ll react at being given orders, some employees take this in their stride, whilst others throw up barriers and objections. Employers like flexible workers who can help out, take on extra responsibilities and do what is right for the good of the company. Be aware that if employers ask this question then it’s likely that your new superiors are looking for someone they can mould into the position favouring less autonomy.

POSSIBLE ANSWER: “No team can work effectively without the guidance and instruction from their superiors, I actively thrive within an environment offering this.”.

How would your work colleagues describe you?

Employers use this question to gauge what others in a working environment think of you and how you are likely to fit in to an existing team dynamic. Employers are trying to build a picture of your character traits and map this with the requirements of their company and/or team. We would say there is no right or wrong answer here however we’d suggest playing it fairly safe and using generic traits that can be applied to the vast majority of working environments.

POSSIBLE ANSWER: “My colleagues would describe me as a hardworking, organised and enthusiastic employee who is dedicated to the job in hand. I like to think of myself as pretty approachable, so they’d probably say I’m a good person to go to when they need help.”.

Do you feel your career has been a success to date?

This question has no real bearing on whether you are capable of doing the job you are applying for or whether you are even the right person for it. Success can only really be measured by the person who it applies to. What one person thinks is successful another may not. I genuinely feel that very few people actually think their career has been a failure.

POSSIBLE ANSWER: “I feel that I have been successful to date and I am more than happy with my career progression. I have always put emphasis on enjoying the job I do and not how much it pays or what benefits I can gain from it.”.

Success is just us learning from our mistakes. Remember it’s OK to screw up!

Has Your Career Been A Success

What part of your job do you dislike the most and why?

As per the ‘what motivates you question’ don’t give answers that are purely motivated by money and benefits (even if that is the case). We all have parts of our job we dislike so be truthful here, but steer clear of any parts of your job that may form part of the job you are applying to! Try to ensure your answer is conversed in a positive and constructive way, your interviewer doesn’t want to hear you moaning about all the things you don’t like.

You could explain how you overcame certain dislikes, i.e.

POSSIBLE ANSWER: “I used to find that producing marketing reports was a difficult and time consuming and I genuinely disliked having to scour for information, it felt like an unproductive use of my time. Then I decided that I would come up with a new system using a series of spreadsheets and tools which streamlined the process and produced better overall reports and in a more timely manner.”.

Or, you could focus on responsibilities you want more involvement with. This is a clever reply as it dodges the direct question of your dislikes and allows you to focus on how you want your career to progress, i.e.

POSSIBLE ANSWER: “I enjoy my current job and I can’t possibly say there are any areas that I outright dislike. However, the company I work for is small and I don’t get much chance to deal with project management very often. This is an area I find exciting and an area I want more involvement with, I feel this opportunity has the potential to offer me that.”.

How have you managed to attend this interview during work time?

Most interviews are conducted during working hours therefore employers will typically use this question to assess your levels of honesty and integrity. It may be that you’re being made redundant or are currently out of work in which case it doesn’t apply. But, if it does, you’re being asked ‘what excuse did you use to get the time off for this interview’. Your answer should show a level of professionalism, avoiding out and out lies like ‘I phoned in sick’ or ‘I told them I had to take my dog to the vets’ these answers won’t cut it here.

POSSIBLE ANSWER: “My existing employer is unaware I’m looking for new positions therefore I’ve told them I have a personal matter to deal with. I gave them a weeks notice and requested that it was taken as unpaid leave, rather than holiday, it didn’t seem right interviewing on company time”.

Why did you leave your last role without having a new role to go to?

If you find yourself out of work whilst applying for new jobs then this question applies to you. Most of us rely on a steady income to pay the mortgage, bills etc., therefore leaving this stability of a job without having anywhere to go is considered irrational behaviour and one that employers will pick up on.

You may have a genuine reason for being out of work, perhaps you were made redundant, were a contractor or needed to look after a sick relative - all genuine reasons. However if the decision was not yours to leave it can go against you, in this instance be sincere, explain the reasons why things didn’t work out and remain positive.

POSSIBLE ANSWER: “I initially joined as a Customer Service Account Manager, however over the last 6 months it has evolved into a pure sales role and one that I’m not comfortable with. I’m happy to handle customer situations and manage sales but our team was purely benchmarked on up-selling products and hitting targets. Customer service suffered as a result of this and I found myself in a highly pressurised sales environment which was not making the most of my skills”.

What is your current salary?

Technically employers shouldn’t ask this question (although many do), they should instead favour the next question which is “What are your salary expectations?”. Businesses are looking to gain the best value for them (rather than always paying what is advertised), therefore your interviewer will ask this question in an attempt to gauge what level of pay rise you are looking for. If the difference between what you are on and what you are looking for is too great then it is likely to count against you. We’d suggest an ambiguous answer here which references what you are looking to earn rather than what you have been earning.

POSSIBLE ANSWER: “My current package falls within the range you are offering. I’d be looking for something towards the top end of the bracket, I’ve been looking at other positions from around £33k so this is my minimum expectation level really.”.

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What are your salary expectations?

Before attending any interviews (or before applying to any jobs for that matter) it’s important to know what your minimum salary expectations are. This will help you with questions like this one but also isolate the right opportunities from the outset (it’s very frustrating for all parties to discover a salary mismatch during an interview and the realisation that everyone’s time has been well and truly wasted).

Our advice for answering this is to be clear with what you expect as a minimum, you can also add a little mystique by making reference to other interviews and jobs you are applying too.

POSSIBLE ANSWER: “I’ve been interviewing and approaching companies with a salary range starting from $35,000 with the highest being $42,000. Money won’t be my deciding factor, however the former figure is the minimum I would need to consider a move.”.

Aren’t you a little overqualified for this job?

When recruiting, employers will question everything that doesn’t sit right or conform to type, this will include your level of experience if out of balance with what the role requires. Let me tell you, recruitment is a drain, it takes time and resources that distract from other goals, therefore employers look for candidates that will give stability and are likely to stay for a long time. Overqualified candidates may appear as desperate, trying to find any position that will pay the bills and will jump ship when something more relevant appears (this is how employers think).

This can be a difficult question to answer therefore you are going to need a strong back story and conviction in your delivery.

POSSIBLE ANSWER: “I may appear to have a lot of experience however I still feel I have a lot to learn, I enjoy being guided by others and working on tasks which assist the company overall. Joining this great company at a lower level can also provide a better view of the inner workings, so, if I was to work my way up I would have a better perspective on the business as a whole.

Can you sell me this pen?

In this classic scene from the film The Wolf of Wall Street, Leonardo DiCaprio who plays former stockbroker Jordan Belfort takes a pen out of his pocket and challenges top sales executives to sell him that pen. 

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Although you may not work in sales this question has been known to crop up in all sorts of interviews and is well known. The purpose of this question is to see how good you are at selling the benefits of a product rather than the product itself and in order to understand the benefits you need to know also know your buyer (or in this case the interviewer).

Ask open questions to understand why they might need a pen, uncover a problem and then solve it by selling the pen. Sounds easy right, well it’s not especially in a pressurised interview situation.

If you’re looking for a quick shortcut try this clever reply which shows quick thinking and initiative…

POSSIBLE ANSWER: (start by taking their pen) “Yep, sure, but what are you going to use to write down my answer? I have a great pen here that I can sell you..”

How well do you cope under pressure?

All jobs carry with them varying degrees of pressure and stress, typically the more seniority you have the more stress and pressure you have to deal with therefore we all need to develop coping mechanisms for dealing with stress and pressure within the working environment.Most jobs carry an element of stress whether it’s working to very tight deadlines or handling lots of different projects and having to manage your time effectively. Your answer to this question should encompass examples of situations where you have operated well under stress and also point out that you get a buzz out of a working in stressful environment as it keeps you mind focused and it assists you in your performance.

POSSIBLE ANSWER: “I actively love working within demanding situations, it gives me a genuine buzz and pushes me to deliver the best work I can, pressurised situations don’t faze me. If these environments do faze you then I believe you probably don’t have the necessary skills in the first place and are therefore out of your depth.”.

What part of this job appeals to you the least?

This question may come later in an interview and is typically used once you’ve let your guard down a little. The interviewer is trying to probe you, gauging your true opinion on the role and uncovering whether it really is the best fit for you.

Make sure when you answer this question you don’t list any job responsibilities that form a major part of the role. Also remain positive, the question is designed to invite negativity so don’t rise to it, use a positive spin when answering.

POSSIBLE ANSWER: “Overall it all looks great to me, but if you were making me pick one responsibility it would probably be the supplier negotiation. The main reason is I like to really get to know suppliers and build rapport, I secure great deals but at times it can be time consuming and can distract from other duties.”.

What do you think of Donald Trump?

The interviewer may bring up politics to assess your interest in current affairs but also to assess whether you are an opinionated person. Your answer is likely to give your interviewer an insight into your values whether they be moral or otherwise and how you address life itself. Politically correct answers aren’t always the right ones. What you need to do is show the interviewer that you have the ability to see and recognise all sides of a debate, that you don’t see things simply in black and white and that you have the ability to debate a subject properly. What you don’t want to do is jump on your high horse and fire off your own political views.

POSSIBLE ANSWER: “He’s not for everyone, but you’ve got to admire his drive! I think he caught the imagination of working class America with policies that people wanted to hear. Only time will tell but personally I preferred him in Home Alone 2.”.

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Why have you been with your current employer for so long?

This one is designed to question your ambition, however there could be many reasons why you’ve chosen to be loyal. Build your answer around the facts relevant to you, perhaps your personal circumstances have changed or you’ve reached a stage in your life where you need to be pushed further. Whatever it is stay true to yourself on this one.

POSSIBLE ANSWER: “I really respect my current employers, they offer a great company and environment to work which is supportive and promotes training and progression, however in recent years things have plateaued and I feel like I need a change and a fresh set of challenges. I am a loyal person and an environment that rewards this.”.

If we hired you how long would it be before you’d expect to be promoted?

If I had to make a sweeping generalist statement I would say that we all want career progression and we want it in the quickest possible time. However you need to tread carefully on this question, avoid sounding over ambitious as this may scare employers off. The simple advice is to not mention any specific timescales as the expectations employers put on promotion timescales may be vastly different from your own.

POSSIBLE ANSWER: “Promotions are a result of ability therefore it is difficult to put an exact time-frame down. If appointed I would look to prove myself within the company, showcasing my abilities and what I can deliver. A promotion is a reward that comes off the back of hard work and demonstrating my skills. A promotion is not a right but needs to be earned.”.

What sort of people do you struggle to work with?

There are always some people who upset a team dynamic, their either too bossy, too lazy, too much gossip (or all of the above). Your interviewer will know that not all employees are created equal, therefore this question gives you an opportunity to once again turn a negative question into one that has a positive spin.

Try to sympathise with your employer and isolate ‘problem employees’ as the ones you can’t work with.

POSSIBLE ANSWER: “I consider myself a very amicable, easy to get along with person therefore I don’t struggle with anyone, however I like to be very productive at work and can find it frustrating if i’m interrupted regularly with non work related chat. Some employees like to waste time and gossip a lot, this is not for me, in this instance I normally have to disengage from such general chit chat to focus on my duties”.

Do you have many interviews lined up?

This is a really good question as it allows you to highlight to employers your employability and gives the impression that you are in demand. The objective here is to make the employer think that you have a number of options on the table. This approach will help you create urgency around your job application and will speed up the overall process and make you a more attractive prospect.

POSSIBLE ANSWER: “I’ve been attending interviews this week and I have a couple more scheduled for next week. I’m not actively applying for any more positions now, I think I have enough in the pipeline to secure a new position within the next 2 weeks.“.

Remember Guy Goma? He had more interview options on the table than most, he turned up for a job interview at the BBC and found himself in an interview of a different kind…

How does this position compare to the others you’ve been applying to?

This is a great question from an employer’s perspective as it helps them gauge how you rate this position over the others you’ve been applying too. In terms of your answer you need to get the balance right, if you sound too over enthusiastic it may come across as desperate, if you underplay it then it may just seem you’re not interested.

A diplomatic answer can help you stand out here.

POSSIBLE ANSWER: “It’s certainly up there, I’ve been interviewing for 4 days now and have a couple more interviews scheduled for next week, each position offers something slightly different, this one is certainly near the top of the ones I’ve been to so far“

What is the biggest weakness of your current boss?

Let’s face it, most of us would like an opportunity to list all the annoying and unprofessional things our bosses do, however this isn’t the forum to vent these frustrations. Your interviewer is probing your professionalism and how you question authority so keep things strictly on point. Remember the person sitting in front of you just might be your boss one day so the aim is to keep things positive and avoid negation.

One tip here is to reverse the question and actually talk about all the great things you wished they did more of.

POSSIBLE ANSWER: “My boss leads by example, she is a real inspiration for the team and takes a hands-on approach to completing projects and getting the job done. She maintains a high level of rapport with her staff and conducts regular one-to-ones. I wouldn’t say she has a particular weakness however we have a big team environment so it can be difficult to benefit from all her knowledge and training”.


Hopefully this information will help you nail that interview and set you on your way to an awesome new career. Now, to be ultimately prepared make sure you read… 7 Questions you MUST ask in your next interview and How to get a job interview.

As Benjamin Franklin once said “by failing to prepare, you are preparing to fail”.

Good Luck people!