name: mentorship
description: Learning roadmaps and career progression tracking - personalized development plans with milestone tracking
agent: advisor
version: 1.0
classification: public
last_updated: 2026-01-26
effort_default: STANDARD

⛔ 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:

typescript 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

name: mentorship
description: Skill building with learning roadmaps, 30/60/90-day plans, certification guidance, and career progression tracking
agent: advisor
version: 1.0
classification: public
last_updated: 2026-01-26
effort_default: STANDARD

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.

Model Tier Routing

This skill uses the three-tier orchestration engine for cost-optimal execution:

Routing Decision Tree:
- Learning guidance and roadmap explanations: Tier 1 (Free) - $0.00 (e.g., "Show learning roadmap")
- Structured 30/60/90 day plans: Tier 2b (Grok 4.1 Fast) - $0.70/1M ← Primary
- Complex certification paths with portfolio planning: Tier 2b (Grok 4.1 Fast) - $0.70/1M (multi-step orchestration)

Why Tier 2b for mentorship?
- Complex multi-phase program generation (30/60/90 planning)
- Large context for certification path orchestration
- Multi-step skill progression logic
- Resource integration (courses, books, projects)
- Cost savings vs. Sonnet: 71% ($0.70 vs $2.40 per 1M)

How it works:
1. You invoke /mentorship with a skill/goal
2. Base Claude's tier selector analyzes planning complexity
3. Simple roadmaps route to Tier 1 (free)
4. Full 30/60/90 plans route to Tier 2b for structured generation
5. Certification paths use Tier 2b for multi-step orchestration

Cost Model:
- Learning guidance: $0 (Tier 1)
- 30/60/90 plan: ~$0.70 (Tier 2b for structured planning)
- Certification path + portfolio: ~$1.40 (full orchestration)

Reference: See docs/skill-tier-integration.md for complete skill mapping.

Pre-flight Checklist (MANDATORY)

STOP! Before executing this skill:

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

Input Directory Structure

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

skills/mentorship/input/
├── 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.

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

skills/mentorship/output/{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)

skills/mentorship/output/{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}",
  "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": []
  }
}

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"

Progress Tracking

Use TodoWrite to display progress:

[ ] Phase 1: Assess - Gather current skills, goals, constraints
[ ] Phase 2: Plan - Create 30/60/90-day milestone structure
[ ] Phase 3: Resource - Research platforms and cert ROI
[ ] Phase 4: Track - Generate tracking template and metrics

Error Recovery

Related Skills

• /clifton - CliftonStrengths analysis
• /career - Job application workflow

Version: 1.0
Last Updated: 2026-01-13
Status: Active