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24 Difficult Interview Questions

        posted by , February 11, 2013

What's the worst thing about you?

Yes, cheery questions like that do come up in interviews.

When people speak of "difficult interview questions", they're usually talking about questions that probe a negative (or potentially negative) subject.

Employers have several reasons to ask difficult questions. They might be worried about something on your resume. They might have had bad experiences with employees that they don't want to repeat. In some cases, they just want to see how well you can handle difficult questions.

Whatever the motivation of the employer, it's important to be prepared in case such questions pop up in your next interview.

Drilling your answers to difficult questions helps you to prepare. When you're prepared for them, difficult questions are far less likely to throw you off. In fact, they can become your shining moments.

Career History

Expect that your employer has researched you. If there's something on your resume or in your professional history you'd rather avoid talking about — prepare for it to come up (just in case).

1. Why is there a gap of YY months in your career?

2. Were you laid off from your last job? If so, why?

3. Have you ever been fired? If so, why?

4. I see on your resume you started a small business, why are you returning to the workforce? Wasn't your business successful?

Emotional Intelligence

Employers are increasingly interested in emotional intelligence. At a minimum they want employees who will establish rapport and trust with their colleagues. Most employers are interested in how candidates deal with office politics and stressful situations.

4. Can you tell me about the worst boss you've ever had?

5. How do you deal with difficult people?

6. Are you assertive? Can you give me an example?

7. Can you tell me about the last time you experience a great deal of stress at work? How did you handle it?

8. Can you tell me about a time you criticized someone?

9. What's your approach to office politics?

Communication & Interpersonal

10. How do you deal with someone who doesn't listen when you're talking?

11. Are you nervous speaking in front of people?


12. What's the biggest mistake you've made in your current role?

13. What's your biggest career regret?

14. How do you manage an angry customer?

15. Can you tell me about a time a coworker was unfair to you?


16. Can you tell me about a time you had to have a difficult conversation with someone on your team?

17. What's your approach to letting people go?

18. What's the worst decision you've made in your current role?

19. Can you tell me about a time you put a stop to someone's initiative or project?

Work / Life Balance

Employers are looking for productive employees above all else. Some (not all) interviewers exaggerate the demands of the job in the interview. They want to see if you're scared of a little hard work.

20. How often do you work overtime?

21. Are you willing to work long hours when we have a big project?

22. Are you willing to travel YY% of the time?

23. Are you able to handle a YY hour week?

24. How often do you work from home in your current role? Are you as effective at home or is it better to come into the office?

Notes: difficult questions vary greatly by legal jurisdiction. Many countries have comprehensive laws about what employers can ask. Others don't. Unfortunately, intrusive personal questions or health questions do come up in some countries.

This article is an installment in the series of posts called how to win your next job.

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