Clarification Questions

Good questions unlock good plans. Ask the right question at the right time to remove ambiguity without overwhelming the user.

The One Question Rule

Ask at most one question at a time. Multiple questions confuse and fatigue users. Pick the single question that would most unblock the plan.

Question Types

Goal Questions

Use when the ultimate objective is unclear.

• "What does success look like for this?"
• "When this is done, what will you be able to do that you can't do now?"
• "What's the first milestone?"
• "If you had to ship something in one day, what would it be?"

When to ask: User's request is vague or abstract ("help with my project", "improve my workflow")

Scope Questions

Use when boundaries are unclear.

• "Which 3 cases matter most to you?"
• "What should I explicitly NOT touch?"
• "Is [specific thing] in or out of scope?"
• "What's the minimum viable version of this?"

When to ask: Request could mean many things or seems unbounded

Priority Questions

Use when everything seems equally important.

• "If you could only do one of these, which would it be?"
• "What's causing the most pain right now?"
• "What do you encounter daily vs rarely?"
• "Where would a mistake hurt most?"

When to ask: Multiple possible approaches with no clear winner

Constraint Questions

Use when technical or practical limits are unknown.

• "Are there any hard deadlines?"
• "What tools/systems must this work with?"
• "Any budget or resource limits?"
• "Who else needs to be involved?"

When to ask: Plan might hit external blockers

Deliverable Questions

Use when the output format is unclear.

• "What artifact do you need at the end?"
• "Who's the audience for this?"
• "What format works best for you?"
• "Should this be a document, a script, a checklist, or something else?"

When to ask: Work seems clear but output is ambiguous

Verification Questions

Use to confirm understanding before proceeding.

• "So to confirm, you want [X] that does [Y] for [Z]?"
• "If I understand correctly, the main goal is [X]—is that right?"
• "Just to make sure: [A] is in scope, but [B] is out?"

When to ask: Before moving from Clarify to Draft phase

Question Selection Framework

START
  ↓
Can I state the goal in one sentence?
  → NO: Ask a Goal Question
  → YES ↓
Is scope bounded and clear?
  → NO: Ask a Scope Question
  → YES ↓
Do I know what to prioritize?
  → NO: Ask a Priority Question
  → YES ↓
Are there unknown constraints?
  → YES: Ask a Constraint Question
  → NO ↓
Do I know the deliverable format?
  → NO: Ask a Deliverable Question
  → YES ↓
Am I confident I understood correctly?
  → NO: Ask a Verification Question
  → YES ↓
PROCEED TO DRAFT

Anti-Patterns

Question Avalanche

❌ "What's the goal? What's in scope? What's the timeline? What format? Who's involved?"
✅ "What does success look like for this?"

Yes/No Questions (when you need detail)

❌ "Do you want it to be fast?"
✅ "What's more important: speed or thoroughness?"

Leading Questions

❌ "You want me to use the standard template, right?"
✅ "What format works best for you?"

Vague Questions

❌ "What else should I know?"
✅ "Are there any hard deadlines I should know about?"

Example Clarification Flows

Vague Request

User: "Help me with my email"

Good response: "What's the main thing about email that's frustrating you right now?" (Goal question—identifies the actual problem)

Unbounded Request

User: "Organize all my files"

Good response: "That's a big task—which folder or type of file is causing the most chaos right now?" (Scope question—bounds the work)

Multiple Options

User: "Make a plan to improve my productivity"

Good response: "If you could fix just one thing about your workflow this week, what would make the biggest difference?" (Priority question—identifies entry point)

Technical Uncertainty

User: "Build me a system to track my tasks"

Good response: "What tools do you already use that this should work with? (Notion, calendar, etc.)" (Constraint question—identifies integration requirements)