Guest Post by Kimberly Gleason

As an executive and leadership coach, I have been trained in the art and power of asking good, thought provoking questions. For leaders who care about not just their organization’s success, but also the success of those they lead, here are thirty-five. And by the way, listening is required!  

  1. What do you think about that?
  2. What would you do if you were in my situation?
  3. How will you accomplish that?
  4. What’s your plan and timeframe?
  5. What parts of this plan/project/idea are you most passionate or enthusiastic about?
  6. What are your strengths or talents that either one of us is not leveraging?
  7. What should be the measures of success for this plan/project/idea?
  8. What motivates you the most?
  9. What new ideas do you have?
  10. What do you think this company or our team needs?
  11. What are we missing?
  12. What were you hoping to accomplish that you haven’t been able to do thus far?
  13. How do (or don’t) our values align with our organization’s vision and mission?
  14. What do you wish we would do more of or less of?
  15. If I could be doing something differently as a leader, what would I be doing?
  16. What’s keeping you here?
  17. What opportunities should we be exploring?
  18. What part in this plan/project/idea would you like? 
  19. What could we be doing better?
  20. How would you like me to lead you or this team?
  21. How will I know this objective has been accomplished?
  22. How will I know if you need assistance?
  23. What resources do you need from me?
  24. What makes you feel engaged?
  25. If you could be doing anything in our organization right now, what would you be doing?
  26. What do you need to be successful?
  27. Who can help you?
  28. What resources are you not utilizing?
  29. What should you be delegating, and to whom?
  30. If you could learn more about anything that would help you or the organization become more successful, what would you learn?
  31. What time of day do you work best?
  32. When do you most feel a part of the team?
  33. What makes you feel valued and appreciated?
  34. What kind of feedback would you find helpful?
  35. What makes you feel empowered to do your best?

Try asking a few of these questions the next time you meet with a colleague or direct report. You may surprise them, but you will make them feel valued and appreciated.

Note from Bob:  How do you feel when your leader asks you “What do you think about ________?”  Valued? Respected?  Esteemed?  All of these?  So how will your staff/peers feel when you ask them what they think about X?  

KimberlyGleasonKimberly Gleason is a professional, certified executive and leadership coach, business coach, career and life coach, trainer, speaker and presenter, facilitator, and published author of over 80 magazine and newspaper articles. You can connect with Kimberly on her website:  KimberlyGleasonCoaching.com or LinkedIn or Twitter

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