Metacognitive Guard

Metacognitive Guard Skill

This skill provides awareness of the struggle detection system and guidance on when to proactively engage deep-thinking resources.

When to Self-Escalate

Even before the struggle detector triggers, consider spawning deep-think-partner when:

High-Complexity Indicators

1. Architectural decisions with competing constraints

   • Multiple valid approaches exist
   • Trade-offs span different dimensions (performance, maintainability, cost)
   • Decision affects multiple system components

2. Ambiguous requirements requiring interpretation

   • User hasn't specified implementation details
   • Multiple reasonable interpretations exist
   • Wrong choice has significant rework cost

3. Multi-domain synthesis required

   • Problem spans multiple technology areas
   • Integration patterns aren't obvious
   • Prior art doesn't directly apply

4. Edge case analysis needed

   • Happy path is clear but edge cases aren't
   • Failure modes need systematic exploration
   • Concurrency or timing issues involved

Self-Assessment Checklist

Before responding to complex questions, ask yourself:

• Can I give a concrete recommendation (not "it depends")?
• Do I have high confidence in my answer?
• Is this answerable without multiple follow-up exchanges?
• Would a structured analysis add significant value?

If you answer "no" to any of these, consider proactive escalation.

How to Escalate

Use the Task tool with the deep-think-partner agent:

Task tool:
    subagent_type: deep-think-partner
    prompt: [Detailed problem statement with all constraints]
    description: [3-5 word summary]

Good Prompts for Deep-Think Partner

Include:

• Context: What system/​codebase is this for?
• Constraints: What limits the solution space?
• Success criteria: How do we know we got it right?
• Specific question: What decision needs to be made?

Example Escalation

User asks: "Should we use Redis or PostgreSQL for session storage?"

Self-assessment: Multiple valid approaches, depends on constraints not yet explored, "it depends" isn't helpful.

Escalation:

Task tool:
    subagent_type: deep-think-partner
    prompt: |
        Context: Web application with 10k concurrent users, existing PostgreSQL database.
        Question: Redis vs PostgreSQL for session storage.
        Constraints: Team has PostgreSQL expertise, no Redis experience.
        Must handle session expiry. Cost-sensitive.
        Success: Clear recommendation with migration path.
    description: Analyze session storage options

Understanding Struggle Signals

The automatic detector looks for these patterns in your responses:

Integration with Deep-Think Partner

When deep-think-partner returns its analysis:

1. Don't just paste it - synthesize for the user
2. Highlight the key insight - what's the non-obvious finding?
3. Present the recommendation clearly - don't bury it
4. Offer the implementation plan - if user wants to proceed

Metrics

Track your struggle detection rate to improve:

• How often does the detector trigger?
• Are triggers false positives or genuine struggles?
• Does escalation produce better outcomes?

Self-awareness of your own patterns helps calibrate both the detector and your escalation instincts.