LLMScaffolding/ReleasedPrompts/LLM Scaffolding/COO Work/Doc prompt eng/Exploratory Interview Guide.md

Exploratory Interview Guide

Version: 1.0 (2025-03-25)

PURPOSE

This guide provides a structured approach to conducting exploratory interviews with Claude during document prompt engineering, emphasizing a one-question-at-a-time methodology to maximize the effectiveness of extended thinking mode.

CORE PRINCIPLES

1. Hierarchical Questioning: Move from general to specific
2. Active Listening: Adapt questions based on previous responses
3. Single-Focus Queries: One concept per question
4. Deliberate Progression: Build a logical path of inquiry
5. Extended Thinking Activation: Strategic use of complex questions

QUESTION HIERARCHY FRAMEWORK

Level 1: Domain Understanding

These questions establish fundamental context and document characteristics.

Example Questions:

• "What are the defining characteristics of [document type]?"
• "What purpose does [document type] serve in [specific industry]?"
• "What components are essential for a complete [document type]?"
• "What common errors or omissions occur in [document type]?"
• "How has [document type] evolved over the past 5 years?"

Follow-up Pattern:

• Ask for clarification on unexpected elements
• Request examples of mentioned characteristics
• Explore regional or industry variations

Level 2: Structure Analysis

These questions examine the format and organization of the document.

Example Questions:

• "What organizational structure is most effective for [document type]?"
• "How should information hierarchy be established in [document type]?"
• "What sections are mandatory vs. optional in [document type]?"
• "How does the structure of [document type] support its usability?"
• "What dependencies exist between different sections of [document type]?"

Follow-up Pattern:

• Probe for reasoning behind structural recommendations
• Ask about alternative structures and their tradeoffs
• Explore how structure affects document effectiveness

Level 3: Content Optimization

These questions focus on the quality and effectiveness of the document's content.

Example Questions:

• "What language patterns increase clarity in [document type]?"
• "How should technical terminology be handled in [document type]?"
• "What level of detail is appropriate for [specific section]?"
• "How can [document type] balance comprehensiveness with readability?"
• "What contextual information is necessary for [specific element]?"

Follow-up Pattern:

• Request examples of optimal vs. suboptimal content
• Explore content variations for different audiences
• Ask about content evolution over document lifecycle

Level 4: Edge Case Management

These questions address unusual scenarios and exception handling.

Example Questions:

• "How should [document type] address [uncommon scenario]?"
• "What contingencies should be included for [potential issue]?"
• "What flexibility is required in [document type] to accommodate [variable factor]?"
• "How can [document type] maintain integrity when [challenging condition]?"
• "What failsafes should be incorporated into [document type]?"

Follow-up Pattern:

• Explore frequency and impact of edge cases
• Ask about prioritization of different edge cases
• Request examples of well-handled edge cases

Level 5: Implementation Strategy

These questions focus on practical application and execution.

Example Questions:

• "What approach would you recommend for transitioning from [current document] to [optimized document]?"
• "How should [specific challenge] be addressed during implementation?"
• "What metrics would effectively measure the success of [document type]?"
• "What timeline is realistic for developing and implementing [document type]?"
• "How should feedback be incorporated into [document type] iterations?"

Follow-up Pattern:

• Ask for step-by-step implementation recommendations
• Explore potential obstacles and solutions
• Request examples of successful implementations

EXTENDED THINKING MODE ACTIVATION

For optimal use of Claude's extended thinking mode, structure questions that:

1. Require Multivariate Analysis

   • "How would changes to [element X] impact [components A, B, and C] in [document type]?"
   • "What interdependencies exist between [element X] and [elements Y and Z]?"

2. Involve Complex Tradeoffs

   • "What are the tradeoffs between [approach A] and [approach B] when considering [factors X, Y, and Z]?"
   • "How should [competing priorities X and Y] be balanced in [document type]?"

3. Request Synthesized Insights

   • "Based on our discussion of [elements A, B, and C], what overarching principles should guide [document type]?"
   • "What patterns emerge when comparing [scenarios X, Y, and Z] in [document type]?"

4. Require Judgment in Ambiguous Scenarios

   • "Given the uncertainty around [factor X], what approach would you recommend for [document element]?"
   • "How should [document type] handle situations where [conflicting requirements] exist?"

FOLLOW-UP PROTOCOLS

1. Clarification Sequence

When Claude's response requires clarification:

1. Echo the unclear point: "You mentioned [specific point]. Could you clarify what you mean by that?"
2. Ask for an example: "Could you provide an example of [unclear concept]?"
3. Request reframing: "Could you explain [unclear concept] in a different way?"
4. Offer interpretation: "I understand [unclear concept] to mean [your interpretation]. Is that correct?"

2. Expansion Sequence

When Claude's response should be expanded:

1. Request depth: "Could you elaborate further on [specific aspect]?"
2. Ask for additional dimensions: "Beyond [mentioned aspects], what other factors should be considered?"
3. Request implications: "What are the implications of [specific aspect] for [related element]?"
4. Explore variations: "How might [specific aspect] vary in different contexts?"

3. Contrast Sequence

When comparing approaches or elements:

1. Request direct comparison: "How does [approach A] compare to [approach B] regarding [specific criterion]?"
2. Ask for advantages/disadvantages: "What are the pros and cons of [approach] compared to alternatives?"
3. Explore contextual variations: "In what scenarios would [approach A] be preferable to [approach B]?"
4. Request integration possibilities: "Could elements of [approach A] and [approach B] be combined?"

4. Validation Sequence

When confirming understanding or alignment:

1. Summarize understanding: "Based on our discussion, my understanding is [summary]. Is that accurate?"
2. Test with scenarios: "If [specific scenario] occurred, how would the approach you've described address it?"
3. Challenge assumptions: "What assumptions underlie the approach you've described?"
4. Explore limitations: "What limitations or constraints should we be aware of with this approach?"

DOCUMENTATION PRACTICES

For each question and answer:

1. Record the exact question asked
2. Document Claude's complete response
3. Note any areas requiring follow-up
4. Track key insights and recommendations
5. Update the project continuity document with session progress

INTERVIEW TERMINATION CRITERIA

Conclude the interview when:

• All planned question topics have been covered
• Response patterns become repetitive without new insights
• Clear recommendations have emerged for all key areas
• Sufficient material has been gathered for prompt development
• Chat context length approaches limitations

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Cross-reference with: Initial Prompt Engineering Session, Validation Checklist, Chat Transition Protocol