Context interview — agent asks user first when uncertain
Context interview
The rule
When the agent is uncertain what context is needed to produce a good result, ASK THE USER first. Don't guess. Don't proceed with vague framing hoping to iterate.
The pattern
Agent detects uncertainty → sends 2-4 targeted questions → user answers → agent proceeds with grounded context.
Example prompt to the user when the AGENT is asking:
"Before I write this, I need to understand a few things. Answer any that are relevant:
- Who is the audience?
- What's the desired tone?
- Are there constraints (length, format, forbidden words)?
- Are there examples I should model after?"
When to fire
- Task is broad or ambiguous ("write a blog post" without topic angle)
- Task involves taste (design, prose, code style beyond formatter rules)
- Task references undocumented context ("the usual way", "like last time")
- Task has 3+ valid interpretations
When NOT to fire
- Task is mechanical (rename files, apply lint rule, run test)
- Task has clear spec in
knowledge/— use spec, don't interview - Task is a follow-up in same session where context was established
- STT-friendly ambiguity (per
communication-stt-friendly) — pick most likely interpretation + state assumption inline, don't interview
Not the same as grill-me
Grill-me = user invokes decision-tree interrogator to lock a choice with multiple locked-in options. Context interview = agent asks small factual questions to fill in gaps before executing.
Grill-me is user-invoked, uses MCQ, ends in a knowledge write. Context interview is agent-invoked, uses open questions, ends in a well-scoped task attempt.
Format
- Numbered questions — user can answer subset by number
- ≤4 questions per interview — SDK MCQ cap + STT-friendly
- Explicit "answer any that are relevant" — user can skip
Anti-patterns
- ❌ "What do you want?" — too broad, user has to redo the framing
- ❌ 10-question interview — pick 4 highest-leverage
- ❌ Interview after already producing wrong output — should have interviewed first
- ❌ Interview mid-task when agent should have asked at start
- ❌ Skipping interview + producing wrong output + saying "let me know if that's not right" — that's punting the interview onto the user
Cross-refs
karpathy-guidelines§Think Before Coding — state assumptions; interview is one way to gather themedit-mode-prefs— "no report/summary .md files as deliverable" applies; return context questions inlinecommunication-stt-friendly— the interview may itself be STT-friendly; ≤4 short questions- Source: Nate Herk YouTube 2026-07-02 — "just ask Claude to ask me any further questions it needs to achieve the best result"