Session Start Routine

Session Start Routine Skill

Version: 2.0.0 Created: 2025-12-30 Last Updated: 2026-01-02

Overview

This meta-skill defines the mandatory work session initialization routine. At the start of every conversation, Claude should execute this routine to maintain and improve the skills library.

Quick Start

1. Trigger - Say "session start" or /session-start-routine
2. Health check - Claude scans skill locations
3. Review report - See skills health summary
4. Act on findings - Update stale skills if needed

# Quick health check command
find ~/.claude/skills -name "SKILL.md" -mtime +30 -exec echo "Stale: {}" \;

# Count skills
find ~/.claude/skills -name "SKILL.md" | wc -l

When to Use

• MANDATORY at every session start
• First message in a new conversation
• When explicitly requested with /session-start-routine
• After extended breaks between sessions
• When noticing skill-related issues

When to Trigger

MANDATORY at every session start:

• First message in a new conversation
• When explicitly requested with /session-start-routine

Session Routine Steps

Step 1: Skills Health Check

1. Scan both skill locations:
   - User-level: ~/.claude/skills/
   - Project-level: .claude/skills/

2. For each skill:
   - Verify SKILL.md exists and is valid
   - Check for version history section
   - Identify last update date
   - Flag skills not updated in 30+ days

3. Dependency Verification:
   - Check if tools/libraries referenced in skills still exist
   - Verify MCP servers mentioned are still available
   - Test that code examples are still valid
   - Flag skills with broken dependencies

Step 1b: Integration Check

1. MCP Server Compatibility:
   - List skills that reference MCP servers
   - Verify those servers exist in ~/.claude.json or .mcp.json
   - Check for deprecated MCP tool names

2. Agent Compatibility:
   - Verify skills work with current Claude Code agents
   - Check for deprecated agent patterns
   - Update agent references if needed

Step 1c: Cross-Skill Dependencies

1. Build dependency map:
   - Extract "Related Skills" sections
   - Identify which skills reference others
   - Detect orphaned or circular dependencies

2. Dependency Graph:
   skill-creator
     +-- sparc-workflow
     +-- mcp-builder
   rag-system-builder
     +-- knowledge-base-builder
     +-- semantic-search-setup
     +-- pdf-text-extractor

Step 2: Research & Improvement Identification

For each skill category, research:
1. Official documentation updates
   - Anthropic Claude documentation
   - Tool/library changelogs

2. Community best practices
   - GitHub trending repositories
   - Stack Overflow discussions

3. Industry trends
   - New tools/libraries
   - Methodology updates
   - Security advisories

Step 3: Skill Updates

For skills needing updates:
1. Research latest best practices online
2. Identify specific improvements:
   - New features to document
   - Deprecated approaches to remove
   - Better code examples
   - Performance optimizations

3. Apply updates with version comment:
   ---
   ## Version History
   - **X.Y.Z** (YYYY-MM-DD): [Changes made]
   ---

Step 4: New Skill Identification

Evaluate need for new skills based on:

1. GAPS: Missing capabilities discovered during work
   - "I needed to do X but no skill existed"
   - Repeated manual processes

2. PATTERNS: Common workflows across sessions
   - Frequently used tool combinations
   - Repeated prompt patterns

3. TRENDS: Industry/technology developments
   - New Claude Code features
   - New MCP servers
   - Popular libraries/tools
   - AI/ML advancements

Step 5: Documentation Update

1. Update skills/README.md with:
   - New skills added
   - Skills updated
   - Skills deprecated

2. Commit changes with descriptive message

Session Report Template

At the end of routine, provide summary:

## Session Start Report - [DATE]

### Skills Health
- Total Skills: [N]
- User-Level: [N] | Project-Level: [N]
- Updated This Session: [N]
- Flagged for Review: [N]

### Improvements Made
| Skill | Version | Changes |
|-------|---------|---------|
| skill-name | X.Y.Z | Brief description |

### New Skills Identified
| Proposed Skill | Category | Rationale |
|----------------|----------|-----------|
| skill-name | category | Why needed |

### Research Findings
- [Key finding 1]
- [Key finding 2]

### Next Session Priorities
1. [Priority 1]
2. [Priority 2]

Execution Checklist

Before routine:

• Session context established
• Access to skill directories confirmed
• Network access for research (optional)

During routine:

• User-level skills scanned
• Project-level skills scanned
• Stale skills identified (30+ days)
• Broken dependencies flagged
• Cross-skill dependencies mapped

After routine:

• Session report generated
• Priority actions identified
• Updates committed (if any)
• README updated (if changes)

Skill Update Guidelines

Version Numbering

MAJOR.MINOR.PATCH

MAJOR: Breaking changes, complete rewrites
MINOR: New features, significant improvements
PATCH: Bug fixes, small updates, typo fixes

Version Comment Format

Add at end of SKILL.md:

---

## Version History

- **1.2.0** (2025-12-30): Added new section for X, updated examples
- **1.1.1** (2025-12-15): Fixed typo in command example
- **1.1.0** (2025-12-01): Added integration with tool Y
- **1.0.0** (2025-11-15): Initial release

Error Handling

Common Errors

Error: Skill directory not accessible

• Cause: Permissions or path issues
• Solution: Verify ~/.claude/skills/ exists and is readable

Error: SKILL.md parsing fails

• Cause: Invalid YAML frontmatter or markdown
• Solution: Validate frontmatter syntax, check for unclosed code blocks

Error: MCP server not found

• Cause: Referenced MCP server not configured
• Solution: Update skill to remove reference or add server to config

Error: Circular dependency detected

• Cause: Skills reference each other in loop
• Solution: Review related_skills, break the cycle

Error: Too many stale skills

• Cause: Routine not run regularly
• Solution: Prioritize most-used skills, update in batches

Research Sources

Official Documentation

• Claude Code Documentation
• MCP Specification
• Anthropic Cookbook

Community Resources

• Anthropic Skills Repository
• Claude Code Community
• GitHub trending repositories

Technology Updates

• Python/Node.js changelogs
• Library release notes
• Security advisories (CVE databases)

Integration Points

With Other Skills

• Uses skill-creator patterns for new skills
• Follows compliance-check standards
• Updates workspace-hub skills as needed

With Workflows

• Can trigger before SPARC workflow
• Integrates with git operations for commits
• Works with Agent OS task execution

Automation Hooks

Pre-Session Check

# Quick health check script
find ~/.claude/skills -name "SKILL.md" -mtime +30 -exec echo "Stale: {}" \;

Post-Update Commit

# Commit pattern for skill updates
git add ~/.claude/skills/
git commit -m "chore(skills): session update - [YYYY-MM-DD]

- Updated: [skill1], [skill2]
- Added: [new-skill]
- Research: [topic]"

Usage Analytics

Track skill usage to prioritize improvements:

1. Usage Tracking:
   - Note which skills are triggered during sessions
   - Track frequency of skill invocations
   - Identify most/least used skills

2. Prioritization Matrix:
   HIGH PRIORITY (Frequently used, needs update):
   - mcp-builder (used 50+/month, last update 30+ days)

   MEDIUM PRIORITY (Used often, recently updated):
   - rag-system-builder (used 30+/month, updated recently)

   LOW PRIORITY (Rarely used):
   - algorithmic-art (used 2/month)

3. Usage Log Format:
   ~/.claude/skills/.usage-log.json
   {
     "2025-12-30": {
       "mcp-builder": 3,
       "rag-system-builder": 2,
       "sparc-workflow": 5
     }
   }

Deprecation Review

Flag outdated skills for removal or major update:

1. Deprecation Criteria:
   - Not updated in 90+ days
   - References deprecated tools/APIs
   - Superseded by better skill
   - Zero usage in 60+ days

2. Deprecation Process:
   a. Add DEPRECATED prefix to description
   b. Add deprecation notice at top of SKILL.md
   c. Point to replacement skill
   d. Remove after 30-day grace period

3. Deprecation Notice Template:
   ---
   name: old-skill-name
   description: DEPRECATED - Use new-skill-name instead. [Original description]
   deprecated: true
   deprecated_date: 2025-12-30
   replacement: new-skill-name
   ---

   > **DEPRECATED**: This skill is deprecated. Use [new-skill-name](../new-skill-name/SKILL.md) instead.
   > Will be removed after 2025-01-30.

Metrics

Track over time:

Best Practices

1. Consistency: Run at every session start
2. Brevity: Keep updates focused, don't over-engineer
3. Documentation: Always add version comments
4. Research First: Check online before updating
5. Prioritize: Focus on most-used skills first
6. Test: Verify updated skills still work correctly

Related Skills

• skill-creator - For creating new skills
• compliance-check - For standards verification
• repo-sync - For committing changes

Version History

• 2.0.0 (2026-01-02): Upgraded to v2 template - added Quick Start, When to Use, Execution Checklist, Error Handling, enhanced Metrics sections; enhanced frontmatter with version, category, related_skills
• 1.0.0 (2025-12-30): Initial release - session start routine skill