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50 Toughest Interview Questions to Ask or to Answer

50 Toughest Interview Questions to Ask or to Answer

By: John Putzier and David Baker

As former outplacement counselors, we created these questions for our clients to practice in advance of their interviewing candidates as part of their interview preparation. These questions should be asked and answered both positively and in job-related terms. This is the first rule of a solid interview process. Try asking yourself some of these interview questions and see how your answers would resonate with you! That will provide you some context to better hiring.

 1. Tell me about yourself.

 2. Why do you want to work here?

 3. What are your strengths?

 4. What are your weaknesses?

 5. What do you know about us?

 6. Why should I hire you?

 7. Why did you (or why do you want to) leave your current employer?

 8. If you could turn back time and live your life over, what would you do differently?

 9. Describe the ideal work environment for you.

10. Tell me about the worst boss you ever had.

11. If you could change one thing about your last (current) job, what would it be?

12. How do you think your coworkers would describe you, both good and bad?

13. How do you think your bosses would describe you, both good and bad?

14. In prior performance reviews, what were your opportunities for improvement?

15. What are your greatest accomplishments so far?

16. Describe yourself in three words.

17. Are you interested in managing or leading others? Why or why not?

18. How do you define success?

19. Besides money, what do you value or need most if you are to have job satisfaction?

20. Have you ever been fired (laid off, outplaced, etc.)? Explain the circumstances.

21. If you gave your last boss a performance review, what would he or she need to change?

22. Do you prefer to work alone or with others? Why?

23. Describe a difficult situation or task that you had to deal with, and how you did so.

24. How do you feel about travel or relocation?

25. Is there anything that would physically or mentally prevent you from performing this job?

26. What other organizations are you pursuing, or are pursuing you?

27. Do you consider yourself to be creative? If so, give some examples.

28. How would you describe your personality?

29. How much are you expecting to earn in this job?

30. How do you feel about incentives, which are heavily tied to performance?

31. How do you feel about psychological tests?

32. How do you feel about drug tests?

33. What are your goals for five years and ten years out?

34. Do you prefer a job with clearly defined tasks, or one that is more self-directed?

35. Do you prefer to work for a man or a woman? Why?

36. How do you feel about working in a diverse workplace (with minorities, for example)?

37. If you could change three things about yourself, what would they be?

38. Do you consider yourself to be a traditionalist? Why or why not?

39. What motivates you?

40. Do you think that people are basically lazy and need to be pushed to perform?

41. Have you ever had to fire someone? Explain why and how you did it.

42. If you could be in your own business, what business would it be?

43. Do you consider yourself to be more of a people person or a taskmaster?

44. What qualities do you think are necessary to be a leader?

45. How long do you anticipate being in this job, or with our organization?

46. Do you believe that success depends more on what you know than on whom you know?

47. How do you perform under stress?

48. Do you keep current in your field? How?

49.  Do you have any role models? If so, who are they, and why are they role models?

50. What more would you like to know about the job, or about this organization? 

Ready To Hire? Do This Next

Now that you’ve got the questions, you need to find the candidates who have the answers you want to hear. Could you use some help with that? Join Monster for free today. As a member, you’ll receive interview advice, hiring tips, special offers, industry trends, and much more. Let Monster help you prepare an interview strategy that makes sense for your business so you can make a strong hire the first time around.

Excerpted from The Everything HR Kit: A Complete Guide to Attracting, Retaining, and Motivating High-Performance Employees by John Putzier and David Baker. Copyright © 2010 John Putzier and David Baker. Published by AMACOM Books, a division of American Management Association, New York, NY. Used with permission. All rights reserved.