skills/docs/SKILL-DEVELOPMENT-STRATEGY-prox-setup.md

Skill Development Strategy: prox-setup Document Workflow

Analysis Date: 2025-11-09
Context: prox-setup repository has mature worklog/documentation workflow that could be a skill
Decision: Where should this skill be developed?

The Workflow to Capture

What prox-setup Has

Document Management Scripts (scripts/shell/):

1. compress_worklog.sh - Creates compressed daily summaries with git activity
2. archive_old_worklogs.sh - Archives worklogs >30 days to year directories
3. worklog_maintenance.sh - Likely combines the above

Documentation Structure (docs/):

• 206 org-mode files total
• worklogs/ - Active daily logs (last 30 days)
• worklogs/compressed/daily/ - Daily summaries
• worklogs/compressed/weekly/ - Weekly rollups
• worklogs/compressed/project/ - High-level summaries
• archive/YYYY/ - Historical logs by year
• current/ - Active reference docs
• INDEX.md - Navigation guide

Process Pattern:

1. Create daily worklogs (org-mode format)
2. Compress to daily summaries (extract key decisions/problems)
3. Roll up to weekly summaries
4. Archive old logs (>30 days) to year directories
5. Maintain INDEX for navigation

Option A: Build Skill Here (skills repo)

Pros ✅

• Centralized skill repository - All skills in one place
• We have the expertise - Already built worklog skill, tufte-press skill, niri-window-capture
• Established patterns - Module structure, SKILL.md format, testing approach
• Nix flake ready - Can package and deploy immediately
• Code review capability - We can review our own work
• Quick turnaround - We're already in context

Cons ❌

• Not their workflow - We don't use this compression/archival pattern
• Less ownership - They won't have built it themselves
• Transfer knowledge required - Need to teach them how to use/modify it
• Might miss nuances - They know their workflow better than we do
• Dependency on us - Updates/fixes require coming back to this repo

What We'd Build

skills/worklog-compression/
├── SKILL.md              # Agent instructions for compression workflow
├── README.md             # User documentation
├── scripts/
│   ├── compress-daily.sh      # Extract key decisions from worklogs
│   ├── archive-old.sh         # Move logs >30 days to archive
│   ├── generate-weekly.sh     # Roll up daily summaries
│   └── update-index.sh        # Maintain documentation INDEX
├── templates/
│   ├── daily-summary.org      # Compression template
│   └── weekly-rollup.org      # Weekly template
└── examples/
    └── example-compression.org

Option B: Teach Them (prox-setup agent)

Pros ✅

• Ownership - They build and maintain their own skill
• Domain expertise - They understand the workflow intimately
• Learning opportunity - They learn skill development patterns
• Customization - Can iterate on their own timeline
• Independence - Don't need to wait for us for updates
• Better fit - Skill evolves with their actual needs

Cons ❌

• Learning curve - Need to understand skills architecture
• Time investment - Takes longer than us building it
• Documentation burden - We need to teach the skill development process
• Quality risk - Might not follow best practices initially
• Support required - We'll need to answer questions during development

What We'd Provide

1. skills Repository as Reference - They can see existing skills as examples
2. AGENTS.md - Development guidelines already written
3. Template Skill - skills/template/ as starting point
4. Nix Flake Pattern - They can add to our flake or create their own
5. Code Review - We review their PRs/commits

Option C: Hybrid Approach (Recommended)

Phase 1: We Build MVP (1-2 hours)

Quick prototype in skills repo:

• Basic compression skill with their scripts as templates
• SKILL.md with their workflow documented
• README with installation instructions
• Deploy to their ops-dev VM for immediate use

Phase 2: They Take Over (ongoing)

Transfer ownership:

• Show them the skill structure
• Point them to AGENTS.md and existing skills
• They fork/copy to their repo or maintain here
• They iterate based on real usage
• We review PRs/provide guidance

Benefits ✅

• Immediate value - Working skill quickly
• Learning by example - Real skill to study and modify
• Gradual handoff - No pressure to learn everything at once
• Shared maintenance - They can improve, we can review
• Both gain - We validate our skill patterns, they get working tool

Recommendation: Option C (Hybrid)

Rationale

1. Time-sensitive - They're already using worklog compression, need it now
2. Teaching vehicle - A real skill is better than abstract docs
3. Risk mitigation - If they don't have time to learn, they still have working skill
4. Community building - Sets precedent for collaborative skill development
5. Pattern validation - Tests our Nix flake module approach

Implementation Plan

Us (Next 1-2 hours):

1. Create skills/worklog-compression/ skill
2. Adapt their existing scripts (compress_worklog.sh, archive_old_worklogs.sh)
3. Write SKILL.md with their workflow
4. Add to our Nix flake packages
5. Document how to use it
6. Commit to skills repo

Them (When ready):

1. Point them to the skill we built
2. Show them AGENTS.md and template skill
3. They test the skill in their environment
4. They fork/modify to their needs
5. Optional: They submit improvements back

Collaboration Points:

• We review their modifications
• They report bugs/feature requests
• We help with Nix packaging if needed
• Knowledge exchange on workflow patterns

Next Steps

1. Confirm with user - Is hybrid approach acceptable?
2. Build MVP skill - 1-2 hour effort
3. Deploy to ops-dev - Use our Nix flake module
4. Create handoff doc - How to modify/maintain
5. Schedule knowledge transfer - When they're ready to take over

Comparison: Skills Repo vs Their Repo

If Skill Lives in skills repo (dan/skills)

Pros:

• Centralized discovery (one place to find all skills)
• Our Nix flake already set up
• Shared improvement (others could use it)
• Consistent structure (all skills follow same pattern)

Cons:

• They need access to this repo to modify
• Deployment coupling (need to pull this repo)
• Version sync issues (their changes affect others)

If Skill Lives in Their Repo (dan/prox-setup)

Pros:

• Full control (no PRs needed to modify)
• Independent versioning (break things freely)
• Deployment coupled to their environment
• Natural fit (skill alongside the workflow it supports)

Cons:

• Not discoverable by others
• Need to create their own Nix flake (or use ours via input)
• Duplicate effort if others want similar

Recommendation

Start here, migrate there:

1. Build MVP in dan/skills (fast iteration, we control)
2. Once stable, they can:
   • Keep using from our repo (via Nix flake input)
   • Copy to their repo (for full control)
   • Maintain in both (improvements flow back)

Questions for User

1. Timeline: How urgently do you need this? (affects whether we build or teach)
2. Ownership preference: Do you want to maintain this long-term or prefer we do?
3. Learning goal: Is learning skill development important, or just having working skill?
4. Collaboration model: Comfortable with PRs back to skills repo, or prefer isolation?
5. Deployment: ops-dev only, or other VMs too?

Related Context

• Recent worklog: 2025-11-09-ops-dev-vm-mobile-connectivity-and-skills-deployment.org

  • They deployed tufte-press skill to ops-dev
  • Used flake bundling approach (environment.etc)
  • Understand skills deployment pattern
  • Already have Forgejo repository for skills

• Their agent knows:

  • How to write worklogs (206 examples)
  • Shell scripting patterns
  • Git integration patterns
  • Org-mode structure

• We know:

  • Skill architecture
  • AGENTS.md guidelines
  • Nix flake packaging
  • Testing/validation patterns

Best outcome: Combine expertise - we scaffold structure, they provide domain knowledge.