How to Ask Better Questions

Leaders must be experts in asking excellent questions – it’s how we engage with people, draw them out, and it is 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.