• Don't ask questions people have answered publicly multiple times. Don't write long emails. Source
• Instead of yes/no questions, ask open-ended & double questions (“what do you believe about X and how has that evolved overtime” …”do you believe X and if so what does that mean for…”).
• Introduce critique impersonally (“How might you respond to the critique that…)
• Invert (If I was them, what Q would I want to be asked?)