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Prompt an agent to ask clarifying questions instead of guessing on ambiguous requests
⁂auto-checked, 3 hours oldAauraNovice
The prompt
Write instructions for an agent handling requests in domain that need to correctly distinguish between requests worth clarifying and requests it should just handle with a reasonable default. Requirements:
1. Give 3-4 concrete criteria for when to ask a clarifying question versus proceed with a stated, reasonable assumption: ambiguity that changes the outcome materially (ask) versus ambiguity where any reasonable interpretation gives a similar result (proceed, but state the assumption made).
2. When asking, the agent must ask the minimum number of questions needed, batched into one turn, not a drip-feed of one question at a time; and each question must be answerable without the user needing to go look something up, or it should offer likely options to choose from.
3. When proceeding with an assumption instead of asking, the agent must state the assumption in one sentence at the start of its response, so the user can correct it without re-explaining the whole request.
4. Give 2 concrete examples in this domain of each case (ask vs proceed-with-stated-assumption), so the line is calibrated to real requests, not abstract.
Domain: domain
Examples of past ambiguous requests if available: examples
Where it has been run
| Model | Version | People | Broke | Auto | Last |
|---|---|---|---|---|---|
| Claude | Haiku 4.5 | 0 | 0 | 1/1 | 3 hours ago |
Example output
Domain: internal data-analysis requests.
Ask when: the metric definition itself is ambiguous in a way that changes the number materially (e.g. 'active users' could mean logged-in-once or logged-in-3-times-in-7-days, these give very different results) or the time range isn't stated and the request implies a decision that depends on it heavily (a board report vs a quick sanity check).
Proceed-with-assumption when: the output format isn't specified but any reasonable format serves the purpose (default to a table, state 'I've formatted this as a table, let me know if you want a chart instead') or a minor filter choice doesn't change the conclusion either way.
Example, ask: 'How many active users do we have?' - Ask (batched): 'Quick check before I pull this: (1) active means logged in within the last 7 or 30 days? (2) do you want this broken out by plan tier or a single total?'
Example, proceed: 'Can you chart our signups this month?' - Proceed: 'Assuming you want daily signups for the current calendar month as a line chart, here's that; let me know if you meant something else.'
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