Best Questions to Ask When Assessing the “Cultural Fit” of a Candidate


When interviewing candidates, job experience and work history are often the area’s most heavily scrutinized. Yet, the extent to which a candidate will effectively fit in with the culture of the hiring organization is almost equally as important. After all, a worker may be experienced and capable, but if they’re dramatically out of step with the overall ethos of the workplace and the organization itself, the probability of successful, productive engagement drops precipitously. With this reality in mind, we offer the following guidance on how to interview for appropriate cultural fit.

In finding a prospective employee who represents a good match for both the role and the organizational culture, hiring managers must pick employees who challenge the status quo thinking and bring new ideas and ways of approaching familiar situations. Managers must studiously avoid hiring people who are too similar to the existing, prevailing wisdom. No “clones” if you will. Following is a list of some probative questions that are proven-effective in helping to determine if a candidate will be a solid cultural match.

  1. What gets you excited about coming to work?
  2. What surprises people about you?
  3. What did you like most/least about your last company?
  4. When was the last time you made a big mistake at work and how did you address your error?
  5. Describe the best/worst team-building exercise you have ever participated in.
  6. If you were going to start your own business, what would it be?
  7. What’s the biggest problem in most offices today?
  8. Where/when/how do you do your best work?
  9. How do you handle stress or tight deadlines?
  10. What three things do you need to succeed in this position?
  11. What kind of events do you attend outside of work hours?
  12. What blogs or websites do you visit regularly?
  13. How would you describe your group of friends?
  14. What do you do for fun?
  15. Are you still friends with any previous colleagues?
  16. How have you changed over the last five years?
  17. What motivates you to do your best work?
  18. How do you prefer to communicate with coworkers?
  19. What has been the most valuable lesson of your professional career?
  20. How will this role challenge you?
  21. Who inspires you and why?
  22. What superpower will you bring to our company?
  23. How do you give/respond to critique?
  24. What three words would a current manager/colleague/direct report use to describe you?
  25. What has been the greatest disappointment of your life to date?
  26. If you do not get this position, what will be your next career move?
  27. Which of our company’s core values do you most/least identify with?
  28. What does work-life balance mean to you? 
  29. What charities are you passionate about?
  30. How do you manage conflict with coworkers?
  31. Describe a time when you exceeded people’s expectations.
  32. What role does kindness/empathy/humour play at work?
  33. What does your decision-making process look like?
  34. When is the last time you took a risk professionally?
  35. Would you rather work alone or with a team?
  36. How would you describe your leadership style?

Obviously, we don’t recommend grilling your candidates with three dozen questions. For help selecting the ones most attuned to your specific organizational culture, speak with a contingent workforce management expert from the nextSource team for help isolating the right questions for your operation.

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