Challenging Interview Questions

What’s a good question that can’t be prepared for?  Sometimes interview responses can seem rehearsed or pre-prepared. Try a sample of the questions below that are designed to be a little bit different maybe a little more challenging and enables you to see how the candidate “thinks on their feet”.

In the interview situation, you can then gauge how candidates react/respond to being asked unexpected questions like the ones below.

  1. Tell me about a time that you failed to achieve goals/targets set at work?
  2. Tell me about a time that you haven’t got on with your immediate colleagues and how did you go about influencing a change.
  3. What do you think about my interviewing skills?  And what would you do differently if you were conducting this interview?
  4. What has being forced into lockdown taught you about yourself and others? What lessons have you learned from the experience?
  5. What critical feedback have you had most recently? Did you feel it was fair and what steps have you made to put this right?
  6. What values do you live your life by? When and how was the last time you demonstrated these? Give me specific examples.  How          would you work with someone who didn’t hold the same values?
  7. Tell me something interesting about yourself that’s not on your CV.
  8. How do you think the interview is going so far and why?
  9. How have you developed yourself personally in the last 12 months? (involvement in an activity hobby educational reading)
  10. What have you got involved in “outside” your comfort zone? Why? And how did you go about getting involved in it?
  11. Describe yourself in 3 words!
  12. What do you do to relax outside of work?
  13. Give me two reasons we should not offer you this job?
  14. On a scale of 1-10 for reliability and commitment what number are you? Give me an example of how you have demonstrated this.
  15. Who have you worked with that has inspired you?  How have you developed to demonstrate those traits?


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