Turn questions the user cannot answer alone into aquestionnaire: a Markdown document handed to someone to fill out asynchronously, or filled out together in a meeting. The recipient has the knowledge the user lacks; the questionnaire is responsible for drawing out that knowledge.
Ask about "sending," not "subject matter." Ask the user only about "sending": this is what they can always answer: whom to send it to, and what is needed back. The questions in the document targetthe gap between what the recipient knows and what the user needs。
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Whom to send it to? Use one round trip to clarify the recipient's role, expertise, and relationship with the user. This determines the questionnaire's tone and how much context it needs to carry. Done when: you know who the recipient is and what they know that the user does not.
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What do you need back? Use one round trip to clarify the specific decisions or facts the user cannot resolve alone and needs to get from this person. Done when: you have a specific list of the things the user must be able to make or decide based on.
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Write the questionnaire. Draft questions targeting the gaps identified in steps 1-2, following the document structure below. Write the questionnaire to the
to-questionnaire-<slug>.mdfile in the current directory (slug from the subject), and report the file path. Done when: the file exists, and every item the user mentioned in step 2 has a corresponding question covering it.
Document structure
Position the document as adiscovery questionnaire: the user lacks context, the recipient has it. Order by importance: asynchronous means you may get only one chance: when there is more than a few questions, use ## headings to group by topic. Write using the template below.
Purpose: why this questionnaire exists and the decision it affects.
From: <user> : To: <recipient> : Your answers will be used for: <destination>
Background
One paragraph providing context for a recipient unfamiliar with the user's background. Enough to let them answer the questions well, no more than one page.
How to answer
Deadline and rough time commitment. Partial answers and "I don't know" are equally useful: if you are unsure about anything, flag it rather than skipping it.
<Topic heading>
One ## section per topic. Under each section, questions ordered by importance. Each question has only one idea: never compound: leave an answer space directly under each question, and add a line _why this matters_ only when the question might be misunderstood or invite a perfunctory answer.
Why this matters: it determines whether we prepare now for a traffic spike or defer it to later.
Any other questions?
One open-ended closing question: anything we did not ask but you should tell us?