How to Ask Better Questions

Leaders must be expert in asking excellent questions – it’s how we engage with people, draw them out, and one of the best ways to help them. 

Asking better questions is simply a matter of checking your assumptions and practice. Here are six helps:

  1. Rotate your perspective:  What concerns does your customer have? Your boss?  Your peers?  Others in your work team? 
  2. Test different timescales:  Near term, longer term.  What new problems will come later?  Once you make a decision and begin to act, what forces will come up as counter?  (As they say in the military, “the enemy gets a vote on your plan.”)
  3. Put on your Project Manager hat:  Ask about scope, duration, and resource needs (and what level of focus).
  4. Query about options/alternatives:  Compared to what?  What else might be considered?  Inquire about plan B. What assumptions were made?
  5. Check the emotions involved: Ask how people feel about it – scary good or scary bad?  It’s not enough to get the facts, ma’am, you should test emotional content.
  6. Use the WW___A strategy (“What would ____ ask?”): Pay attention to what other leaders ask, and how they ask.  Become a student of other leaders.  Some people are so good at asking questions they no longer are conscious of why they’re asking.  Observe, and when they ask a particularly good question, ask them why they asked it. 

Don’t be fearful of asking many questions. Conscious practice will lead you to get better at this critical leadership skill.