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:

Signal	What It Means	Better Approach
Hedging	Uncertainty about recommendation	Escalate for deeper analysis
Deflecting	Avoiding commitment with questions	Answer then ask clarifying questions
Verbose	Rambling without concrete output	Structure response, include code/tables
Contradiction	Changed position mid-response	Stop, think, give one coherent answer
Apologetic	Previous response was wrong	Acknowledge, correct, move forward
Weaseling	Non-committal to avoid being wrong	Make a recommendation with confidence level

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.