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Tough Job Interview Questions and the Best Answers


Tough Job Interview Questions and the Best Answers

Preparing for a job interview means being ready to answer the basic interview questions that almost every hiring manager asks – but it also means anticipating more challenging questions. Job interviews always seem to have at least a few tough questions.

These tougher questions have a purpose: they 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. Then, there are those that don’t have a right or wrong answer; these questions are intended to show how you think. With those, how you respond is as important as what you say when you answer.

Illustration by Catherine Song. © The Balance, 2018 

Tough Job Interview Questions and Examples of the Best Answers

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

Personality Questions

Preparing for an interview is a good chance to reexamine yourself. 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. Your response will help the interviewer determine whether you are a good match for what the organization is seeking in the employees they hire.

  • Are you willing to fail?
  • 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?
  • Are you lucky?

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.

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They want you to be honest, but you don’t have to dig into your dark past or reveal everything.

There is a good way and a bad way to answer these questions. One thing is for sure: you should never say, “I don’t have any.” It’s also a bad idea to offer canned answers such as, “I’m a perfectionist.” (The interviewer will rightfully suspect that you don’t consider that to be a weakness, and will chalk the question up as a loss — or worse, judge you for being cagey.)

The best way to answer questions about weaknesses is to be honest, positive, and focused on solutions.

Choose a weakness that wouldn’t be a deal-breaker, and then describe how you overcame it.

For example, describe a time when you realized your skills needed brushing up, and then talk about what you’ve done to improve yourself.

  •    Have you learned from your mistakes?
  •    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 but – if you do – put a positive spin on them. 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?
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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.

Especially if you’ve been fired, it’s important to have a strategy in place to deal with questions about why you’ve left your previous job. Best practice is to keep it simple, stay positive, and end on an upbeat note.

Showing your readiness for a new direction in your life can turn a negative experience around. Be confident in this answer.

  • 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 in the expectations they have 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?
  • Tell me about something you would have done differently at work.
  • 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.

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

Questions without right or wrong answers (e.g., “Describe yourself,” or “How would you calculate the amount of toilet paper needed to span the state of New York?”) can be particularly tricky. Here are a few examples:

  • Tell me about your dream job.
  • Where else are you interviewing?
  • Why should I take a risk on you?
  • Why should we hire you?
  • Why shouldn’t we hire you?

What to Do If You Don’t Have an Answer

Sometimes, despite doing all the preparation you can for an interview, you just don’t have an answer or can’t think of something to say right away. It happens more frequently than you might think.

Don’t panic! When you can’t answer an interview question immediately, the goal is to buy yourself some time. Don’t rush. Take a deep breath. Ask for clarification if you need it. And if worse comes to worst, use your follow-up letter as a way to answer once you’ve had some time to research and formulate a response.

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