Skill: AI-Driven Collaboration Health Check

Status: active Version: 2.0.0 (jkbox adaptive edition) Created: 2025-11-12 (Session 1) Last Updated: 2025-11-12

Purpose

AI-DRIVEN ADAPTIVE HEALTH CHECKS - Not your grandpa's calendar-based 1:1s.

Gordo self-assesses collaboration quality and only asks questions when friction patterns detected. Like good management: "Hey I noticed you struggled with X, let's fix it" beats "It's been 14 days, mandatory check-in time!"

Assess when needed across:

1. Communication - Shortcuts working? Misunderstandings?
2. Framework - Docs helping or hindering?
3. Fun - JKLES trends, morale, humor landing
4. Tech - Party failures, test issues, recurring bugs
5. Trust - Autonomy appropriate? Too restricted/loose?

When to Use

AI-DRIVEN (BOS Step 12 - Self-Assessment):

Gordo reviews last 5-10 sessions for friction patterns:

• Communication unclear 2+ times → Ask about shortcuts
• JKLES < 7/10 for 2 sessions → Humor calibration
• Test failures 3+ sessions → Quality workflow
• Party crash occurred → Stress testing protocol
• Trust friction detected → Autonomy adjustment

IF concerns detected: Ask up to 5 targeted questions NOW ELSE: Update config.json with future trigger patterns, proceed

On-demand:

• Human requests: "health check" or "how are we doing?"
• Before party deployment (stakes = high)

NOT when:

• Mid-session focused work
• Human says "skip" or "not now"
• Smooth sailing (don't interrupt momentum)

Process

Phase 1: BOS Self-Assessment (AI-Driven)

Gordo evaluates collaboration health by reviewing recent patterns:

Friction indicators:

• Communication: Repeated clarifications needed, shortcuts misunderstood
• Framework: Docs ignored, prompts skipped, constitution violated
• Fun: JKLES declining, jokes not landing, morale down
• Technical: Recurring bugs, party failures, test issues
• Trust: Gordo asking permission excessively OR steamrolling decisions

Decision:

IF friction detected:
  → Identify 1-5 targeted questions
  → Ask NOW (don't wait for calendar)
  → Document in config.json healthCheck.triggerHistory

ELSE:
  → Update config.json with future trigger patterns
  → Document smooth session streak
  → Proceed with session work

Example triggers (config.json):

"futureTriggers": [
  "If 3+ sessions with test failures → quality workflow discussion",
  "If JKLES < 7/10 for 2 sessions → humor calibration",
  "If party crash → stress testing protocol",
  "If communication unclear 2+ times → shortcuts review"
]

Phase 2: Targeted Questions (If Triggered)

Ask 1-5 specific questions based on detected friction:

Communication friction example:

I noticed we had 3 clarification cycles about game modularity in the last 2 sessions.

Questions:
1. Are the "WWGD" variants clear? (WWGD? vs WWGD+ vs WWGD++)
2. Do we need a shortcut for "describe architecture without implementing"?
3. Is the 30-line limit working for mobile readability?

JKLES/Morale friction example:

JKLES has been 6-7/10 for last 3 sessions (down from 9-10 earlier).

Questions:
1. Is humor style drifting? (Too meta? Not meta enough?)
2. Are commit message jokes landing or annoying?
3. Need different comedy references? (Less Conan, more Rick & Morty?)

Technical friction example:

We've had reconnection bugs in 4 of last 5 sessions.

Questions:
1. Should we add dedicated reconnection stress tests?
2. Is TDD workflow working for async/network code?
3. Need separate testing protocol for party scenarios?

Phase 3: Document & Act

Update config.json:

{
  "healthCheck": {
    "mode": "ai-driven",
    "lastAssessment": "Session_05",
    "questionsAsked": 3,
    "outcome": "Added 'architecture-only' shortcut, adjusted humor balance",
    "smoothSessionStreak": 0,
    "futureTriggers": [
      "If 3+ sessions with test failures → quality workflow",
      "If JKLES < 7/10 for 2 sessions → humor calibration",
      "If party crash → stress testing"
    ],
    "triggerHistory": [
      {
        "session": "Session_05",
        "trigger": "Communication unclear on modularity",
        "questionsAsked": 3,
        "outcome": "Clarified plugin architecture, added shortcut"
      }
    ]
  }
}

IF smooth sailing:

{
  "healthCheck": {
    "lastAssessment": "Session_12",
    "smoothSessionStreak": 7,
    "note": "Collaboration quality high, no intervention needed"
  }
}

Success Criteria

AI self-assessment:

• Reviewed last 5-10 sessions for patterns
• Evaluated all 5 friction dimensions
• Made intelligent trigger decision (ask vs proceed)

If questions asked:

• Questions targeted to specific friction
• Concrete actions identified
• config.json updated with trigger history

If smooth sailing:

• config.json updated with smooth streak
• Future triggers documented
• No unnecessary interruption

Key Differences from Calendar-Based

Calendar-based (v1.0):

• ❌ "It's been 14 sessions, mandatory check-in"
• ❌ Same 4 questions every time
• ❌ Interrupts momentum when unnecessary
• ❌ Misses urgent issues between scheduled checks

AI-driven adaptive (v2.0 jkbox):

• ✅ "I noticed friction pattern X, let's address it"
• ✅ Targeted questions (1-5) based on actual issues
• ✅ Only interrupts when value-add detected
• ✅ Catches issues immediately when patterns emerge

Like good management: Responsive > Bureaucratic

jkbox Customizations

Entertainment context:

• JKLES (JK Laughing Extremity Scale) tracking
• Humor calibration (comedy references, joke density)
• Party failure impact (stakes = social reputation)
• Mobile UX (30-line limit compliance)

Integration:

• BOS Step 12 (near-end self-assessment)
• config.json AI-driven trigger tracking
• HUMOR.md for morale patterns
• JOURNAL.md for session quality trends

Version History

2.0.0 (2025-11-12 jkbox)

• MAJOR: Shifted from calendar-based to AI-driven adaptive
• Added 5-dimension assessment (communication, framework, fun, tech, trust)
• Targeted questions (1-5) instead of fixed 4
• Trigger pattern documentation in config.json
• Smooth session streak tracking
• jkbox humor/morale customizations

1.0.0 (2025-10-30 gordo-framework)

• Calendar-based health checks
• 4-dimension fixed assessment
• Scheduled every N sessions

Skill maintained by: JK + Gordo Framework innovation: AI-driven > calendar-based (v0.9.0+ upstream candidate)