Turn something the user can't answer alone into a questionnaire : a Markdown document they hand to one person to fill in async, or fill out together over a meeting. The recipient holds knowledge the user lacks; the questionnaire pulls it out of them. Grill the send, not the subject. Interview the user only about the send , which they can always answer: who it goes to, and what they need back. The questions in the document then target the gap between what the recipient knows and what the user needs. 1. Who is it going to? Ask, in one exchange, the recipient's role, expertise, and relationship…