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The Hardest Interview Questions


Whenever there is an important interview coming up, some will be fastidious in their preparation, while others will just ‘shoot from the hip’’ and act exactly as they are with no frills. There is no right or wrong way; some prefer to prepare, others don’t.

After all, when it comes to the hardest interview questions, it is impossible to cover every aspect of questioning you are likely to get.

And a further consideration is the interviewer may suspect you have prepared some stock answers. I know; I could usually tell if they had. That would put me off the candidate straight away, as it feels false.

the hardest interview questions

Do Some Questions Have Anything To Do With Your Suitability?

The most difficult interview questions to answer will be those that have little to do with you or your experience in the workplace. You could then argue that they have little to do with your suitability for the position. And you would probably be right.

There is a trend these days to adopt a policy of trying to make the candidate feel uncomfortable at the interview. It is fashionable amongst some companies and their representatives.

Creating the questions…

Companies, self-titled consultancies, have been set up. They are where some people seem to find some pleasure in creating these questions. Designed to make the candidate feel out of their depth and generally bad.

They convince companies looking for staff that these questions and their irrelevant answers are going to ‘sort out the weak links.’ No, they won’t.

hardest interview questions

An Example

This approach to the candidate coming to an interview seemed to start somewhere in the early 70s. Tony, a very good friend of mine, had the experience. We both came out of university, both tried a job which didn’t suit us, and both decided to change our line of work. He was in IT; I was in another field.

He went for an interview with a rather ‘blue’ American computer company. At the interview, they tried this approach, and the interviewer asked him to sell them an ashtray sitting on the desk. He got up, walked to the door, turned, and said, “Have I come here to sell multi-million dollar hardware or cheap and rather nasty glass?”

A Sign Of What Was Coming?

The tables had been turned, and the interviewer was floored. Tony just left. He got a job with a rival company and, within a year, had sold his big-dollar system. ‘Big Blue’ missed out on that one with their ‘trendy’ approach. Perhaps a sign of what was to come for them.


It seems we are stuck with this ‘aren’t we cute’ interviewing technique. What are the questions you need to look out for? Let’s take a look at a few. I have split them into certain categories. Because some questions that could actually be useful for the interviewer, they may therefore be relevant and useful.

Some That May Offer Some Insight Into Your Personality

What are your strengths?

An oldie but quite a reasonable thing to ask.

What are your weaknesses?

Usually follows or precedes the previous question. Again a bit tired but still could have some relevance.

Your greatest achievement?

If you are a young candidate, it’s likely you haven’t had one, so pointless, really. Older candidates may have made a difference somewhere, so it is easy to answer. But don’t over-elaborate. It looks cheesy.

the hardest interview question

Describe a Failure

Once again, the opposite of what you have just been asked. A question I always thought to be a little pointless. If you had one, are you likely to bring it up at any interview? Of course not. So what does it gain?

Why Did You Apply For This Job?

Easy to answer that one; there aren’t any tricks involved.

What Can You Bring to the Team?

Again a relevant question that only takes you to list your strengths.

Why Should We Choose You?

I refer to my previous answer.

Which of your attributes will support you in this role?

I again refer to my previous answer.

Describe a Time When You Worked Under Pressure

You may have one of those situations to recount, though be careful. What you see as pressure they may see as a standard day. You could argue that those questions could be relevant to the success of your application. However, it is also fair to say that by this time in the interview, they may have already made their mind up. I’ll come back to that.

But what about those questions that were concocted on a bad day in Disneyland?

Questions That Have No Relevance To You Or Your Ability To Do The Job

  • If You Were A Vegetable, What would You Be and Why?
  • If You Were a Fruit, What Would You Be and why?
  • Or, If You Were a Flavor of an Ice Cream, what would You Be and Why?

And before we go any further, these are actual questions. But I haven’t finished yet.

  • Using three words, describe yourself. (‘Stupid for Applying’ is not the answer they are looking for or thought that Tony would answer.)
  • Do You Think the CEO likes this company? Not sure how that has any relevance whatsoever.

hardest interview question

Sometimes You Get the ‘Philosophical One’ such as… What Do You Want To Get Out of Life?

But there are some questions you may be asked that are tough to answer that have relevance. They could throw a spotlight on your character. As the hardest interview questions go, these are worth looking at and attempting a basic answer. These include…

How Long Would You Expect To Work Here if Hired?

A tricky one to answer in many ways. Putting a number on it could be counterproductive. Safer to say something like ‘as long as both parties are happy’ should suffice.

Does Anything Irritate You About Co-workers?

Again, it could be awkward. The department they are interviewing for might have a tricky member of staff who can upset people. The best answer is also the best attitude in life. Maintain your beliefs and actions but adjust how you handle them and tread softly with some people.

What sort of person would you be looking for if you were hiring?

Ouch, that can be awkward. It is no good just reeling out a list of your own positives. That is too easy to see through. Some, yes, but then also include others that demand a little more experience. Then you could follow up if necessary with your hope to be able to grow into those.

What Did You Think of the Last Company You Worked For?

Simple. Never disparage, but also don’t praise too highly. It may prompt a question like ‘if it was that good, what are you leaving’?

What Would Be Your Dream Job?

Again the need to tread carefully. A ‘blank page’ answer is best here. Just remarking that your dream job would be one where the work is challenging, your colleagues a pleasure to work with, and the management inspiring.

Do You Think Your Working Life Has Been Successful So Far?

You need to answer yes for this one. Otherwise, ‘no’ could be assumed to be an admission of failure. You can pull out some ways where you think what you have done has made a difference and, thus, in your eyes, are successful.

Would You Ever Feel Successful In This Job?

That is being dangled in front of you to see if you’re likely to achieve something and then relax and lower your standards. The answer has got to confirm that you’re not the one that would measure success. You would just keep trying to achieve and improve. It is for others to judge your success.

Those are just a few, but there are a lot more. But these last seven all have some relevance, unlike some of the previous examples.

The Early Minutes

Let me go back to a point I made earlier about the first few minutes of the interview. There is conflicting research, as there usually is, about what happens in the first few minutes of an interview. Some say that the interviewer makes their mind up in the first five minutes. Others say that it can be as short as 90 seconds.

In my experience of interviewing, I would say that within 90 seconds to two minutes, I had formed an opinion. That opinion could change, of course, but it rarely did. It was it based on…

  • Appearance.
  • Positivity in the greeting?
  • A Feeling That They were Relaxed (even if they weren’t).
  • The Clarity of the first few sentences they spoke.

It never relied on what sort of vegetable or flavor of Ice Cream they thought they were or should be.

the hardest interview question guide

The Hardest Interview Questions

These will always be the ones that are relevant to the position you are applying for. If you get the others, you can take my buddy Tony’s stance. Or you can smile and just skip over them.

Employers want professional people who can fill the role. They don’t care whether they are a carrot, an orange, or a chocolate fudge sundae. So, here are some items that can help you as you walk in the door for your interview.

A nice briefcase is always a good start; I would suggest the quality Tassia Luxury Leather Executive Case Attache Briefcase. And if you have to make notes, a nice pen will give you a professional image; something like the Parker IM Fountain Pen always works well.

And don’t get soaked to the skin on the way to the interview by making sure you take the Lilyxin Premium Automatic Compact Umbrella Windproof with you.

Need More Interview Info And Advice?

For your all-important interview, check out my advice on How Would You Describe Yourself, What Are Your Career Goals, Answer Why Best Candidate Position, How Do You Handle Stress, What Are You Most Proud Of, and of course, the Best Questions To Ask In An Interview to help How Do You Handle Conflict,?

Or, how about the Strengths And Weaknesses For Job Interviews, Why Do You Want To Work Here, How To Answer What Are You Passionate About, Answering Tell Me About Yourself In Interview, What Makes You Unique? and my Why We Should Hire You to better prepare.

If you’d like to brush up on your reading, these great books are available online. Try Hiring Squirrels: 12 Essential Interview Questions to Uncover Great Retail Sales Talent, or maybe Amazing Interview Answers: 44 Tough Job Interview Questions with 88 Winning Answers for that final preparation.

It doesn’t hurt to be extra prepared, and reading Get That Job!: The Quick and Complete Guide to a Winning Interview, How to Answer Interview Questions: 101 Tough Interview Questions, or my favorite the INTERVIEW with DESIRE and GET HIRED!: How to Ace the Interview, Sell Yourself & Get Your Dream Job can help ace that interview.

If you’re not quite as prepared as you should be, I found additional advice online on the STAR Method. Simply check out The STAR Method Explained: Proven Technique to Succeed at Interview, or The STAR Interview: How to Tell a Great Story, Nail the Interview and Land Your Dream Job.

And the perfect notebook to prepare for your interview is the STAR METHOD INTERVIEW: Interview Journal: Notebook designed for job seekers to use as a guide for interview prep and as a tool for interview questions and answers during interviews available in 2023.

Final Thoughts

To some, it will be one thing to someone else, something completely different. But just like the first 90 seconds or so of the interview might give them an insight into you. Being asked some of those questions gives you an insight into them and who you might be working for.

All the very best with your future Interviews!

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