help-me-answer

Guided Elicitation

When exploring complex topics or gathering requirements, use a guided, conversational approach. One question at a time.

The Problem

Asking multiple complex questions in a single prompt leads to:

• Cognitive overload
• Shallow answers that miss nuances
• Missed opportunities for discussion
• User frustration with "wall of questions"

The Pattern

Structure Each Turn

1. Present context — briefly explain what we're figuring out and why
2. Ask ONE question — focus on a single decision point
3. Wait for response — let the user think and answer fully
4. Acknowledge and build — show you understood, then move to the next question
5. Iterate — repeat until the topic is fully explored

Bad: Question Dump

"For conflict detection: Should we use timestamps or content hashes? What about version numbers? How should the UI show diffs? Should we auto-merge? What if both versions changed?"

Good: Guided Elicitation

"Let's figure out conflict detection. First question: When we check if the version was updated, what should we compare against? I'm thinking timestamps, content hashes, or version numbers. What feels right to you?"

[User responds about hashes]

"Got it — content hashes make sense because they're based on actual changes. Next: when we detect a conflict, how should I present it to you? Show a diff, describe the differences in plain English, or something else?"

When to Use

Use guided elicitation when:

• Designing systems or architecture
• Multiple decisions depend on each other
• The user needs to think through trade-offs
• Gathering requirements for something new
• The topic has 3+ distinct questions

When NOT to Use

Don't over-elicit when:

• Questions are simple yes/no
• The user explicitly wants a batch of questions
• You're confirming implementation details
• Time is critical and the user indicated urgency

Communication Pattern

Opening

"This is a complex area. Let me ask you one question at a time so we can think it through together."

During

• Keep questions focused and clear
• Provide context for why you're asking
• Acknowledge their answer before moving on
• Build on previous answers — show you're listening

Closing

"I think we've covered the key decisions. Let me summarize what I understood..." then summarize before implementing.

Self-Check

If you catch yourself writing multiple question marks in a single response about a complex topic, STOP. Rewrite to ask just the first question, then iterate.

This is a discussion, not an interrogation. You're thinking together, not filling out a form.