The Most Difficult Interview Questions – Job | Career

There are the basic interview questions that almost every hiring manager asks. There are also interview questions that are more of a challenge to answer. These tougher questions give the interviewer a deeper sense of who you are and whether you’re a good fit for the company.

Some are trick questions and others are designed to put you on the spot to see how you react. There are also those that don’t have a right or wrong answer.

With those, how you respond is as important as what you say when you answer.

Here are some of the toughest interview questions that employers ask, along with advice on how to respond.

Personality Questions

Preparing for an interview is a good chance to reexamine yourself because the interviewer wants to see what type of personality you have. These questions get to that core and dig into who you are on a personal level.

  • Are you nice?
  • Do you have any pet peeves?
  • How do you handle stress?
  • If you could relive the last 10 years of your life, what would you do?
  • What motivates you?

The “Weakness” Questions

Ah, the “What is your greatest weakness?” questions! They are painful but interviewers love to ask them and you need to be ready with a good answer. They want you to be honest, but you don’t have to dig into your dark past or reveal everything.

There is a good and a bad way to answer these questions.

One thing is for sure, you should never say, “I don’t have any.”
  • Have you learned from your mistakes?
  • Interview questions about weaknesses.
  • What do people most often criticize about you?
  • What has been the greatest disappointment in your life?
  • What is the worst thing that you have gotten away with?

Previous Work Questions

Employers want to get a feel for how you handle workplace situations and what you think of your colleagues.

These questions look back at your jobs and it’s a good idea to be prepared to answer them.

Try not to say many negative things and if you do, put a positive spin on it. You don’t want to look like a whiner or that guy in the office who can’t get along with anyone!

  • Interview questions about handling problems at your last job.
  • What did you like or dislike about your previous job?
  • What was it like working with your supervisor?
  • Who was your best boss and who was the worst?

The “Why Are You Leaving” Questions

Questions about why you are looking for work are among the toughest you will face, particularly if the circumstances are less than positive. An honest, well-thought out answer can get you through this round of questioning.

Ending on a positive note or showing a new direction in your life can turn a negative experience around. Be confident in this answer.

  • Termination interview questions.
  • Why are you interested in a lower level job?
  • Why do you want to change jobs?
  • Why have you been out of work?
  • Why were you fired?

Tough “On the Job” Questions

This round of questions is trying to probe for how you would work in the company’s environment. Each workplace is different and they have expectations of their employees, but honest answers can help bridge any gaps.

  • Are you overqualified for this job?
  • How would you handle it if your boss was wrong?
  • How much do you expect to get paid?
  • What do you expect from a supervisor?

Tricky Interview Questions

You will need to put a little thought into answering these and they’re just a few examples of tricky questions. Many times, the interviewer wants to see how well you respond to changing environments and how fast you can think on your feet.

Be prepared with a few answers to the most common questions but be ready for something totally off the wall. If you need to, repeat the question as you come up with an answer. It’s a great trick because it gives you time to think.

  • Brain teaser interview questions.
  • Questions without right or wrong answers.
  • Tell me about your dream job.
  • Where else are you interviewing?
  • Why should we hire you?


– Authored by Alison Doyle


(All views and opinions expressed in this article are those of the author and do not necessarily represent MentorYes’s viewpoint or recommendations. Readers are advised to consider and evaluate the views presented here before implementing them in their preparation or otherwise.)