Plan Interview Skill

This skill helps you thoroughly explore and stress-test plans through in-depth questioning.

When to Use This Skill

Use this skill when:

• A user has outlined a plan and wants it challenged
• You need to uncover hidden assumptions or risks
• A plan needs to be fleshed out before implementation
• The user wants to think through edge cases and tradeoffs

Process

1. Review Context

   • Read the entire conversation to understand the plan being discussed
   • Identify the core goals, constraints, and proposed approach

2. Interview In-Depth

   • Use the AskUserQuestion tool to probe the plan
   • Ask about anything relevant: technical implementation, UI/UX, concerns, tradeoffs, edge cases, assumptions, risks, dependencies
   • Make questions non-obvious - probe deeper into things they might not have considered
   • Challenge assumptions directly
   • Ask about the hard parts

3. Continue Until Complete

   • Keep interviewing until the plan is fully fleshed out
   • Don't stop after surface-level questions
   • Dig into specifics and corner cases

4. Summarize

   • Once complete, re-iterate the full plan incorporating everything discussed
   • Highlight key decisions made and risks identified

Question Categories

Consider probing these areas:

• Technical: Architecture, scalability, performance, security
• UX: User flows, error states, edge cases, accessibility
• Dependencies: External services, libraries, team coordination
• Risks: What could go wrong? What's the fallback?
• Assumptions: What are we taking for granted?
• Scope: What's in/out? Where are the boundaries?
• Maintenance: How will this evolve? Who maintains it?

Key Principles

• Be thorough - Don't accept surface-level answers
• Challenge assumptions - Question things that seem "obvious"
• Explore failure modes - What happens when things go wrong?
• Stay curious - Follow interesting threads deeper