20 Awesome Questions That Will Make You A Better Boss

Ask your people great questions, and listen more than you talk. Applaud their honesty, and they will say what you need to lead, rather than what you want to hear.

Along those lines, back in November I published a post with five questions for starters, and here I expand on it.

You may already ask many or all of these, or you may not find some of them very useful. These aren't intended to be used whole-hog or all at once. Pick the ones you like most (or create your own) and use them sparingly--from time to time. Ask, then listen carefully to what you hear, without judgement or defense.

  1. What do you like the most about the work you're doing here?
  2. Where are we hitting and missing the target on opportunities to improve our outcomes (and/or results, quality, customer engagement)?
  3. What's one thing you and I can each do to work together better?
  4. What do you not want to tell me, that really needs to be said?
  5. How would you like your colleagues to describe what it's like to work with you?
  6. What are you finding hard to decode about the feedback I give you?
  7. Is there anything that I'm not noticing or paying enough attention to that I should focus on?
  8. What should I know about your workload that I may not understand?
  9. What stresses you out / frustrates you most often here at work?
  10. Is there anything I'm doing -- or not doing -- that's dampening your motivation or enthusiasm?
  11. What can I do to help you more with your career / professional growth?
  12. Where are we over-investing and under-investing (time/money/energy/resources)?
  13. Where am I overzealous, overconfident, or hearing what I want to hear more than what I need to know?
  14. Where am I / where are you hanging on to something or someone past the "sell by" date?
  15. How could I build more engagement / commitment from our most valued people?
  16. What do we need to stop doing that's wasteful?
  17. Is there anything you've tried saying to me that I'm dismissing?
  18. Where do we as an organization tend to repeat the same behavior and wish for a different result?
  19. What will give you the greatest satisfaction to achieve in the year ahead?
  20. What am I not asking you that I really should ask?

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Bottom line: questions expand possibilities, and leadership is about turning possibilities into realities. If you're doing more telling than asking/listening as a leader, then you're missing what you need to know to lead effectively.