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25 Tough Interview Questions and their Types

25 Tough Interview Questions and their Types

Congratulations on having found the needle in the haystack. You have already made it farther than many struggling job seekers. You are now getting ready to face the panel of seemingly harmless individuals – the interviewers. You have made copies of your resume, neatly filed all your degree certificates while carefully camouflaging the transcript with an excess of Ds, and practiced your suave smart look a million times in the bathroom mirror. You have read about the job description, you have had enough years of preparation about your field and you have even read up a few commonly asked interview questions.

Then why the knot in the stomach still?

Well, ‘coz there is an extremely unnerving quality about interviews. It’s unpredictability!

No matter what you do and how well you prepare, there could always be a few doozies out there that can make your head go for a spin, and not in a good way. Then what’s the point of this apparently discouraging spout? To let you in on an interviewer’s handbook of horrors!

Let’s start with a claim – interviewers are just people! Keep telling yourself that and you will realize that they too are probably just relying on experience and well hashed techniques of finding who fits in Cinderella’s shoes. They have a fixed amount of time and only a certain number of ways whereby they can assess your talents. And that it is not necessary for you to read their minds but rather enough to be confident and honest about your responses. Remember you are just competing with people who are probably suffering from similar heebie-jeebies as you are.

So let’s talk about the different kinds of interview question categories, there could be, and move on to a few examples of the real testers gathered from other’s experiences.

Types of tough interview questions with examples


All about you

Why should we hire you? What is the worst weakness you have which is really not a disguised strength? What happened to your grades in your third year first semester? Why were you fired from your last job?

You know your background. So you know how it got shaped the way it did. So be prepared with quick and honest responses. Hesitation and dilly dallying will indicate deception.

Behavioral questions

How do react to situations?

Are you a team player? How did you handle a disagreement? What are your complaints about your last job? What would you say if we told you we won’t be able to promote you in the next five years?

These questions test your response to society, which in this case is your workplace. Your responses should be aimed at working with others and resolving conflicts with diplomacy while not getting pushed over.

Technical questions

You are being interviewed for a particular position which requires a specific kind of an expertise. Like your ability to teach a class when you are interviewing for an instructor position, your know how on computer programming when hoping to fill in a coder position, your talent at making a sale when looking at a Marketing position and so on.

These questions will be designed to test your knowledge of the subject matter and shouldn’t be scary really as long as you have had enough of studying and experience under your belt. And honestly, if you don’t know a response, just say you don’t and move on. And whatever you do, never lie on that resume of yours. Being caught red handed is worse than playing dumb!

Problem Solving

The panel will most likely try to test out your ability to come out of a pickle, not literally ‘coz that would be weird – why waste all that pickle!

Anyway, the aim is to find out your thinking process when you are trying to find a solution to a problem. Do you attack it with brute force? Do you try to come up with creative ways to resolve it?

These problems may have nothing whatsoever to do with your future job. So prepare yourself to put on your thinking cap and when asked, think aloud. Really, most of the time they don’t care about the solution as much as they do about your approach.

  • Can you think out of the box?
  • Can you think fast?

Try this one that an applicant was asked while interviewing for Apple. If you were a pizza delivery man, how would you benefit from scissors?

The answer is hidden somewhere in this article. Yes we want you to read the whole article!

Market Sizing and Case Questions

This is a toughy and is usually there to test out your logical and analytical skills. They hand you a real life problem and ask you to solve it using your training thus far. Mostly employed in Consulting, Tech and Investment Firms, the idea is to test your intelligence and the ability to handle the stress of pressure.

As with many other question types, they really don’t care about the solution as much as they do about your thinking style. Like when Goldman Sachs decided to quiz a candidate with this one – How many square feet of pizza is eaten in the US each year? (Glassdoor).

On its face it sounds like an absurd question ‘coz really what business is it of yours to know what your neighbor is having for dinner!

But really if you started thinking aloud and began with the number of people who live in the country, how much of an entire pizza is one person likely to consume and how many times in a month are they likely to buy pizza, you would be getting somewhere logical. Just guesstimate the size of an average pizza and there you go, you are suddenly a marketing wiz!

Tricky questions

Sometimes they may throw a few questions in to gauge your response to a curve ball. Think on your feet and respond such that you don’t come off as plastic while also staying away from being brutally honest.

If you don’t get this job, what’s your backup plan? (Quora)

Getting on my knees and begging! No, please don’t say that. Just let them know that it would be disappointing since this is your first choice and that you will continue looking for another position.

They are just looking for a smart, believable and positive answer.

Bottom line. Don’t ever try to appear to be someone you are not. It is hard to dislike a candidate who is not just well prepared but is also honest (to a reasonable degree!). Who needs a manipulative coworker anyway!

Moving on to taste the thunder of some brainteasers out there. (Read Top Fresher’s Interview Questions and Funny Interview Questions)

Samples of Tough Interview Questions


All about You

  1. Tell us about yourself.
  2. What’s the most interesting thing about you that we wouldn’t learn from your resume alone? (Vault)
  3. What are you looking for in a job?(Dougsguides)
  4. How would you explain a gap in your employment?
  5. Where do you see yourself in the next five years?
  6. Tell us about your proudest moment in your employed life.


Behavioral questions

  1. Describe a situation in which you were able to use persuasion to successfully convince someone to see things your way.(Clairmont Graduate University)
  2. Tell us about an instance when you had to deal with a difficult boss or a coworker.
  3. Describe a long-term project that you managed. How did you keep everything moving along in a timely manner? (The Muse)
  4. Give me an example of a time when you had to make a split second decision. (Clairmont Graduate University)
  5. What do you prefer – close supervision or loose supervision?


Technical questions

  1. If ads were removed from Youtube, how would you monetize it? (Google Interview for Associate Account Strategist – Glassdoor)
  2. What technical websites do you follow? (Information Technology Technical Questions –
  3. Describe the most complex project you have managed. (Quora)
  4. What skills do you need to have, as a teacher, to make teaching more effective?
  5. How would you explain your research to a 10-year-old?


Problem Solving

  1. Teach me something I don’t know in the next five minutes. (Quora)
  2. Would you rather fight a horse-sized duck or fifty duck-sized horses?
  3. What do you want to be when you grow up?


Market Sizing and Case interviews

  1. Your nephew runs a lemonade stand. Yesterday was Monday and he was open from 2pm – 5pm, and sold 2 cups. What should he do differently tomorrow? (Mckinsey)
  2. How would you go about advising a hypothetical client on commercializing a teleportation device that they have invented? (Vault)
  3. How should a nuclear plant deal with waste products? (Vault)


Tricky questions

  1. What is it about this company that you think needs improvement?
  2. How long are you willing to fail at this job before you give up? (US News)
  3. Do you prefer learning or earning? (Glassdoor)

Giving an exhaustive list of questions would be like being able to read the minds of every person on this planet. In other words, impossible. However, with what you have read so far, you probably have a fair idea of the different directions you can expect your interviewer to wander off to.

So get smart and research the company and job type you will be appearing for and walk in that room with a big smile, an air of confidence and a halo above your head. They’d be signing up to join your fan club by the end.

Good Luck and the answer is just as much as anyone else would need a pair of scissors!
Sources: 1,2,3,4,5,6,7,8

Watch this video to learn how you can become an entrepreneur at a young age

Rakhi Acharyya
About Rakhi Acharyya
Rakhi is a freelance writer, a Physics PhD from Michigan State University, an ex-teacher and a former employee of Corporate America. Follow her on Twitter.

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