- Check for understanding by asking What & Where questions: What do you expect to happen? Where should we start? - Determine direction by asking How: How this will work? How do you achieve that? - Assess alignment via engagement: Are you willing to try this? Is there a different way? 1. Don’t ask questions on an impulse, figure out what matters why to you, first. 2. Review if your question is based on unchecked assumptions and resolve those first. 3. Keep asking the question in different settings and contexts to explore it properly.