Status: Active Updated: 2026-01-30 Focus: Ensuring documentation and workflows are executable by AI agents
Overview
This skill evaluates project health from an AI-agent perspective - not just whether docs are well-written for humans, but whether future Claude Code sessions can:
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Understand the documentation without ambiguity
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Execute workflows by following instructions literally
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Resume work effectively with proper context handoff
When to Use
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Before handing off a project to another AI session
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When onboarding AI agents to contribute to a codebase
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After major refactors to ensure docs are still AI-executable
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When workflows fail because agents "didn't understand"
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Periodic health checks for AI-maintained projects
Agent Selection Guide
| "Will another Claude session understand this?" | context-auditor | Checks for ambiguous references, implicit knowledge, incomplete examples
| "Will this workflow actually execute?" | workflow-validator | Verifies steps are discrete, ordered, and include verification
| "Can a new session pick up where I left off?" | handoff-checker | Validates SESSION.md, phase tracking, context preservation
| Full project health audit | All three | Comprehensive AI-readiness assessment
Key Principles
1. Literal Interpretation
AI agents follow instructions literally. Documentation that works for humans (who fill in gaps) may fail for agents.
Human-friendly (ambiguous):
"Update the config file with your settings"
AI-friendly (explicit):
"Edit wrangler.jsonc and set account_id to your Cloudflare account ID (find it at dash.cloudflare.com → Overview → Account ID)"
2. Explicit Over Implicit
Never assume the agent knows:
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Which file you mean
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What "obvious" next steps are
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Environment state or prerequisites
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What success looks like
3. Verification at Every Step
Agents can't tell if something "feels right". Include verification:
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Expected output after each command
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How to check if a step succeeded
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What to do if it failed
Agents
context-auditor
Purpose: Evaluate AI-readability of documentation
Checks:
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Instructions use imperative verbs (actionable)
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File paths are explicit (not "the config file")
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Success criteria are measurable
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No ambiguous references ("that thing", "as discussed")
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Code examples are complete (not fragments)
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Dependencies/prerequisites stated explicitly
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Error handling documented
Output: AI-Readability Score (0-100) with specific issues
workflow-validator
Purpose: Verify processes are executable when followed literally
Checks:
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Steps are discrete and ordered
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Each step has clear input/output
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No implicit knowledge required
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Environment assumptions documented
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Verification step after each action
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Failure modes and recovery documented
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No "obvious" steps omitted
Output: Executability Score (0-100) with step-by-step analysis
handoff-checker
Purpose: Ensure session continuity for multi-session work
Checks:
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SESSION.md or equivalent exists
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Current phase/status clear
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Next actions documented
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Blockers/decisions needed listed
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Context for future sessions preserved
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Git checkpoint pattern in use
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Architecture decisions documented with rationale
Output: Handoff Quality Score (0-100) with continuity gaps
Templates
AI-Readable Documentation Template
See templates/AI_READABLE_DOC.md for a template that ensures AI-readability.
Key sections:
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Prerequisites (explicit environment/state requirements)
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Steps (numbered, discrete, with verification)
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Expected Output (what success looks like)
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Troubleshooting (common failures and fixes)
Handoff Checklist
See templates/HANDOFF_CHECKLIST.md for ensuring clean session handoffs.
Anti-Patterns
1. "See Above" References
# Bad
As mentioned above, configure the database.
# Good
Configure the database by running:
`npx wrangler d1 create my-db`
2. Implicit File Paths
# Bad
Update the config with your API key.
# Good
Add your API key to `.dev.vars`:
API_KEY=your-key-here
3. Missing Verification
# Bad
Run the migration.
# Good
Run the migration:
`npx wrangler d1 migrations apply my-db --local`
Verify with:
`npx wrangler d1 execute my-db --local --command "SELECT name FROM sqlite_master WHERE type='table'"`
Expected output: Should show your table names.
4. Assumed Context
# Bad
Now deploy (you know the drill).
# Good
Deploy to production:
`npx wrangler deploy`
Verify deployment at: https://your-worker.your-subdomain.workers.dev
Relationship to Other Tools
| project-docs-auditor
| Traditional doc quality (links, freshness, structure)
| Human readers
| project-health skill
| AI-agent readiness (executability, clarity, handoff)
| Claude sessions
| docs-workflow skill
| Creating/managing specific doc files
| Both
Quick Start
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Full audit: "Run all project-health agents on this repo"
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Check one aspect: "Use context-auditor to check AI-readability"
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Before handoff: "Use handoff-checker before I end this session"
Success Metrics
A healthy project scores:
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Context Auditor: 80+ (AI can understand without clarification)
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Workflow Validator: 90+ (steps execute literally without failure)
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Handoff Checker: 85+ (new session can resume immediately)
Projects below these thresholds have documentation debt that will slow future AI sessions.