Difficult Interview Questions

Difficult Interview Questions

When The Heat Is On—How To Stay Cool Answering Hot Interview Questions

After you’ve gotten through the standard questions, get ready to take some heat.  Interviewers like to see you sweat, so they have some tricky, difficult questions up their sleeves to see how you react when the pressure is on.  With social media, they also know a lot more about you than you may suspect. If you’ve had some strange phone numbers with no voicemail on your phone lately, it could be a prospective employer checking out your voicemail message.  While you were doing your homework checking out the company website, they have been checking up on you, too.  Here are ten tough made-to-make-you-squirm interview questions and tips for great answers.

  1. “Why were you fired from you last job?”  If you were supplying your home office with company copy paper and pens or drinking on the job, it will most likely come out in a reference check or background check.  If you weren’t fired, the question itself will measure how you handle false accusations—get defensive or stay cool?  Taking responsibility and learning from your mistakes may be enough for a second chance.
  2. “What was your biggest failure at work?”  We all have failures, but don’t get tripped up on “biggest.”  A small one will do, and remember to end the story with lessons learned and how you benefitted from the experience.
  3. “Which one of your co-workers is the most difficult to get along with, and why?” “I get along with everyone,” won’t do.  If you put all your co-workers in a line with your “BFF” at the front, someone will be at the end.  Attribute the difficulty to your work styles.  Don’t get personal or blame it on gender or ethnicity.  You don’t want to be characterized as a discrimination suit waiting to happen.
  4. “On a scale of 1 to 10, with 10 being the highest, how honest are you?”  You’re a 10.  That’s the only answer.   Anything less and you’ve just said you’re at least dishonest 10 percent of the time.   Interviewers like to follow that question with, “Tell me a time when your honesty was tested on the job.”   Have an example of how you triumphed over temptation.
  5. “What will we find as a result of your background check?”  This is an easy question if you’ve been an upstanding citizen.  Even though employers are not supposed to consider arrests or moving violations, DUIs, etc., they can show up on background checks.  If there is a potential time-bomb quietly ticking, it’s better to reveal it than say nothing.  Honesty is always the best policy.
  6. “Why should we hire you?”  You think you’re great and awesome and totally cool, but those are not reasons to hire someone.  This is where you match your skills, experience, values and accomplishments to the job, with the key being how you can add value to the position and company.  Show them how they will get a great return on their investment once you are on board.
  7. “Describe your perfect boss.”   This is very tricky, because their traits will say something about your strengths or weaknesses.  Want someone who leaves you alone?  You may not be a good team player or open to constructive feedback.  Do you need someone who is available to answer questions and give frequent feedback?  You may be insecure, indecisive and need constant approval.  Go back to your company research and how you work best and find a happy medium.
  8. “If you were stranded on a desert island and could wish for three things, what would they be?”  This is a values and problem-solving question.  Many people pick survival items.  Few ask for a boat or helicopter for rescue.  While matches and water will help for awhile, a boat off the island solves the problem.
  9. “Your resume states that you are the Senior Manager of Public Relations at your current job.  Your LinkedIn and Facebook profiles list you as a Supervisor.    Which one is false? “  Gotcha!  If you inflated your position, you’re trapped.  And you just flunked question #4.  Be sure your information matches online and on paper.
  10. “If we find out in a few months you’re not right for the job, how much money would it take for you to resign your position?”  Zappos actually offers a cash payout to new hires who don’t work out if they voluntarily resign.  No dollar amount you come up with is correct.  It’s best to say that if that were the case, you would expect your manager to be honest and see if you could work out any problems.

Be prepared for anything.  Be honest and keep answers job related.  Turn weaknesses or failures into strengths and lessons learned.  Your first comment can be, “That’s an interesting question,” and then take a few moments to collect your thoughts and come up with your best answer.

Mary Nestor-Harper, SPHR, spent over seven years as a human resources director and is a career coach, consultant and freelance writer focusing on how to land your dream job in a tough employment market.


  • Lydia Ramsey

    This is an extremely valuable article for anyone facing the tough interview process. I hope it is widely read.

  • Marynh

    Thanks for your comment, Lydia. With a tough job market, answering tough questions with ease helps a candidate appear well prepared and confident.   Feel free to share the article with your friends and contacts.

    Mary Nestor-Harper, SPHR