⛔ DUAL-PATH ROUTING - READ THIS FIRST

STOP. This skill requires the advisor agent for complex requests.

Identity check: If you are NOT the advisor agent AND your request is complex (personalized roadmaps, career progression, 30/60/90 planning) → DELEGATE NOW:

Task(subagent_type="advisor", prompt="Execute mentorship skill. Request: {user_request}")

DO NOT proceed if you lack advisor expertise for:

• Personalized learning roadmaps
• Career progression planning
• 30/60/90-day goal setting
• Certification path planning

Path 1 - Simple (Tier 1/Haiku): General learning path information

• "What certifications are available in security?"
• "What's a good learning progression for DevOps?"
• Routes directly, no delegation needed

Path 2 - Complex (Advisor): Personalized roadmaps

• "Create a 90-day learning plan for me"
• "Build my career progression strategy"
• Requires advisor delegation

FOR AI AGENTS: Career development and skill building mentorship. Load when: user mentions "learning roadmap", "30/60/90 plan", "certification path", "skill building", "career development", "portfolio projects"

Mentorship & Skill Building Skill

Structured learning roadmaps with certification guidance and progress tracking.

Chain Map

/mentorship (command — base-claude, haiku)
    │
    ▼
phases/00-workflow.md (orchestrator — advisor, sonnet)
    │
    │  Reference: workflows/skill-building.md (supplemental methodology)
    │
    ├→ phases/01-assess.md  → metadata.json             [advisor]
    │
    ├→ phases/02-plan.md    → LEARNING-ROADMAP.md       [advisor]
    │                       (+ ALTERNATIVE-PATHS.md in job mode)
    │
    ├→ phases/03-resource.md → RESOURCES.md             [advisor]
    │                        (+ JOB-SEARCH-STRATEGY.md in job mode)
    │
    └→ phases/04-track.md   → PROGRESS-TRACKER.md       [advisor]
                                  │
                                  ▼
                            private/output/mentorship/{Goal}-{YYYY-MM-DD}/
                            ├── metadata.json
                            ├── LEARNING-ROADMAP.md
                            ├── RESOURCES.md
                            ├── PROGRESS-TRACKER.md
                            ├── ALTERNATIVE-PATHS.md    (job mode only)
                            └── JOB-SEARCH-STRATEGY.md  (job mode only)

Pre-flight Checklist (MANDATORY)

STOP! Before executing this skill:

• Read this SKILL.md completely
• Detect mode: Learning Roadmap vs Certification Prep vs Portfolio Building vs Job Preparation vs Career Progression
• Identify target skill/domain
• Determine timeline (30/60/90 days)

Input Directory Structure

Place career/background materials in private/input/mentorship/:

private/input/mentorship/
├── resume.md                    # Resume (markdown preferred)
├── resume.pdf                   # Resume (PDF format)
├── strengths-report.pdf         # CliftonStrengths or other assessments
├── portfolio-links.md           # Links to projects, GitHub, etc.
├── career-goals.md              # Career aspirations and timeline
└── current-skills.md            # Current technical/professional skills

File format notes:

• Resume works best as markdown (.md) for easy parsing
• PDFs are supported for formal documents
• Use descriptive filenames for multiple people (e.g., resume-jane.md, resume-john.md)

What to include:

• Current role and experience level
• Technical skills and certifications
• Career goals and target roles
• Learning constraints (time, budget)
• Preferred learning style

Core Philosophy

Free First: Prioritize free learning platforms before paid options.

Hands-On: Theory without practice is worthless. Labs, projects, CTFs.

ROI-Focused: Certifications should provide career value, not just credentials.

Portfolio > Certifications: Real projects demonstrate skills better than certs.

Alternative Paths: Job-focused plans MUST include entry-level alternatives.

Incremental Progress: 30/60/90-day structure prevents overwhelm.

Critical Rules

1. Always research current info - Certification costs, requirements change frequently
2. Free platforms first - TryHackMe, HackTheBox, PortSwigger before paid courses
3. Portfolio > Certifications - Real projects demonstrate skills better than certs
4. Realistic timelines - Account for work/life constraints
5. Always include alternative paths - Every job-focused plan MUST include entry-level alternatives, lateral moves, and backup strategies

Mode Detection

4-Phase Workflow

+------------+     +------------+     +------------+     +------------+
|   ASSESS   |---->|    PLAN    |---->|  RESOURCE  |---->|   TRACK    |
|            |     |  30/60/90  |     |            |     |            |
+-----+------+     +-----+------+     +-----+------+     +-----+------+
      |                  |                  |                  |
      v                  v                  v                  v
   Current           Milestone         Platform +         Progress
   Skills +          Structure         Cert ROI           Metrics
   Goals                               Analysis

Phase 1: ASSESS (Current State)

Gather from user or infer:

1. Current Skills - What do they know already?
2. Target Goal - Where do they want to be?
3. Timeline - 30, 60, or 90 days?
4. Constraints - Work hours, budget, prerequisites?
5. Learning Style - Videos, reading, hands-on, structured courses?

Assessment Questions:

• What's your current role/experience level?
• What specific skill/domain are you targeting?
• How many hours per week can you dedicate?
• What's your budget for courses/certs?
• Do you prefer structured courses or self-directed learning?

Phase File: phases/01-assess.md

Phase 2: PLAN (30/60/90 Structure)

Create phased learning plan:

Days 1-30: Foundation

• Core concepts and fundamentals
• Platform onboarding
• Initial quick wins (beginner certs if applicable)
• Build learning routine

Days 31-60: Building

• Intermediate concepts
• Hands-on labs and practice
• Community engagement
• First portfolio project

Days 61-90: Application

• Advanced topics
• Major certification (if applicable)
• Portfolio projects
• Real-world application

Phase File: phases/02-plan.md

Phase 3: RESOURCE (Platforms + Certs)

Use WebSearch for current information:

Free Platforms (Prioritize)

Certification ROI Analysis

For each certification, research:

• Current cost (exam + training)
• Prerequisites
• Renewal requirements
• Market value (job postings requiring it)
• Time investment

Common Security Certs (verify current pricing):

• CompTIA Security+
• CompTIA Network+
• OSCP (OffSec)
• CEH (EC-Council)
• CISSP (ISC2)

Phase File: phases/03-resource.md

Phase 4: TRACK (Progress Metrics)

Establish tracking system:

Milestone Tracking

• Week 1: Platform setup, first module complete
• Week 2: Core concepts understood
• Week 4: Foundation phase complete
• Week 8: Building phase complete
• Week 12: Application phase complete

Metrics to Track

• Hours studied per week
• Modules/courses completed
• Labs/challenges solved
• Portfolio projects finished
• Certifications earned

Session Notes Format

Date: YYYY-MM-DD
Hours: X
Topics: [what you studied]
Completed: [modules/labs finished]
Blockers: [what you're stuck on]
Next: [what to focus on next session]

Phase File: phases/04-track.md

Output Structure

EXACTLY these files. No extras.

Standard Learning Roadmap

private/output/mentorship/{Goal}-{YYYY-MM-DD}/
├── metadata.json           # Learning progress tracking
├── LEARNING-ROADMAP.md     # Full 30/60/90 plan
├── RESOURCES.md            # Platforms, courses, certifications
└── PROGRESS-TRACKER.md     # Milestones and tracking template

Job Preparation Mode (add these)

private/output/mentorship/{Goal}-{YYYY-MM-DD}/
├── (all standard files above)
├── ALTERNATIVE-PATHS.md    # Entry-level alternatives, lateral moves, backup strategies
└── JOB-SEARCH-STRATEGY.md  # Companies, job boards, networking, salary research

DO NOT create: README.md, summary files, or any files not listed above.

metadata.json Schema

{
  "goal": "{learning goal}",
  "target_role": "{target job/skill}",
  "mode": "{detected mode}",
  "started_at": "YYYY-MM-DDTHH:MM:SS",
  "timeline_days": 30|60|90,
  "hours_per_week": 0,
  "phase": "assess|plan|resource|track|complete",
  "current_day": 0,
  "milestones": {
    "completed": 0,
    "total": 0
  },
  "certifications": {
    "target": [],
    "completed": []
  },
  "learning_platforms": [],
  "portfolio_projects": [],
  "key_gaps": []
}

Web Search Requirements

ALWAYS use WebSearch for:

• Current certification pricing and requirements
• Latest platform content/paths
• Job market skill demands
• Industry trends

Search patterns:

• "{certification} exam cost {current_year}"
• "{certification} prerequisites requirements"
• "best free {skill} learning platforms {current_year}"
• "{target_role} required skills job postings"

Error Recovery

File Management

What belongs in skills/mentorship/docs/:

• How-to guides for using this skill
• API or integration reference documentation
• Command reference and workflow explanations
• Troubleshooting guides
• Setup and configuration guides

What does NOT belong here:

• Audit reports or assessment logs → delete (commit messages capture purpose)
• Bug fix notes → delete (git blame shows what changed and why)
• Progress tracking files → update /private/docs/active-tracker.md instead
• Books/PDFs → See private/docs/book-catalog.md for discovery
• Engagement output → /private/output/mentorship/
• Engagement input → /private/input/mentorship/
• Working notes from development → delete (git history captures work)

Skill data locations:

• Input data: /private/input/mentorship/
• Output data: /private/output/mentorship/
• Reference materials: See private/docs/book-catalog.md (search by tag or domain)

Version: 2.0 Last Updated: 2026-02-08 Status: Active Framework: Intelligence Adjacent (IA) Structure: Universal Prompt Structure v2.0