---
name: mentorship-program
description: "Designs mentorship programs with matching criteria, meeting structures, goal frameworks, and progress tracking."
allowed-tools: Read Write Glob
metadata:
  author: matthewhitcham
  version: "1.0"
---

# Mentorship Program

## When to Use This Skill

Use this skill when you need to:
- Design a structured mentorship program with matching, goals, and tracking
- Create mentor-mentee frameworks for a community, company, or paid program
- Build meeting structures and conversation guides for mentoring relationships
- Establish a formal mentorship offering as a product or community benefit

**DO NOT** use this skill for coaching programs (one-to-many), masterminds (peer-to-peer), or consulting arrangements. This is for one-on-one mentorship with clear developmental goals.

---

## Core Principle

A MENTORSHIP PROGRAM WITHOUT STRUCTURE BECOMES COFFEE CHATS THAT FIZZLE OUT — CLEAR GOALS, DEFINED CADENCE, AND PROGRESS MARKERS TURN GOOD INTENTIONS INTO ACTUAL GROWTH.

---

## Phase 1: Brief

### Required Inputs

| Input | What to Ask | Default |
|-------|------------|---------|
| **Program purpose** | "What outcome should mentees achieve through this program?" | No default — must be provided |
| **Duration** | "How long will each mentorship pairing last?" | 3 months |
| **Meeting cadence** | "How often should mentor and mentee meet?" | Bi-weekly, 45 minutes |
| **Program type** | "Is this paid, free, internal, or community-based?" | Paid program |
| **Pool size** | "How many mentors and mentees do you expect?" | 10-20 pairs |

**GATE: Confirm the brief before proceeding.**

---

## Phase 2: Program Design

### Matching System

Define matching criteria:

```
## Mentor Requirements
- [Minimum experience level]
- [Industry or skill expertise]
- [Availability commitment]
- [Communication style preferences]

## Mentee Requirements
- [Current level]
- [Specific goals]
- [Time commitment]
- [Coachability indicators]

## Matching Criteria (ranked by priority)
1. Goal alignment — mentee's goal matches mentor's expertise
2. Industry overlap — similar enough for relevant advice
3. Availability — schedules compatible for regular meetings
4. Communication style — both prefer similar formats (calls, async, video)
```

### Program Timeline

```
Week 0: Applications open → matching → introductions
Week 1: Kickoff meeting — set goals, expectations, cadence
Weeks 2-10: Regular meetings following the session guide
Week 11: Progress review and celebration
Week 12: Program close, feedback collection, next steps
```

### Meeting Structure

```
## Standard Meeting Agenda (45 min)
1. Check-in: Wins since last meeting (5 min)
2. Progress update: Status on action items (10 min)
3. Core topic: This session's focus area (20 min)
4. Action items: 2-3 specific next steps (5 min)
5. Scheduling: Confirm next meeting (5 min)
```

**GATE: Present the program design for approval.**

---

## Phase 3: Build

### Deliverables to Create

1. **Mentor application form** — experience, expertise, availability, motivation
2. **Mentee application form** — goals, current level, challenges, availability
3. **Matching worksheet** — scoring matrix for pairing decisions
4. **Welcome packet** — expectations, communication guidelines, meeting template
5. **Goal-setting worksheet** — SMART goals for the mentorship period
6. **Session guide** — agenda template with suggested topics per meeting
7. **Progress tracker** — milestone checklist for both mentor and mentee
8. **Feedback forms** — mid-program check-in and end-of-program evaluation

### Goal-Setting Framework

```
## Mentorship Goal Worksheet

**Primary goal:** [What the mentee wants to achieve in 3 months]
**Why now:** [Why this goal matters at this stage of their business]
**Success metric:** [How you will know the goal is achieved]
**Biggest obstacle:** [What has prevented achieving this before]
**Mentor support needed:** [Specific ways the mentor can help]

**Milestones:**
- Month 1: [Milestone]
- Month 2: [Milestone]
- Month 3: [Milestone]
```

### Communication Guidelines

- Respond to messages within 48 hours
- Reschedule meetings at least 24 hours in advance
- Keep meeting notes in a shared document
- Respect boundaries — mentorship is not 24/7 access
- Escalation path if the pairing is not working

---

## Phase 4: Polish

### 1. Program Management Tools

```
## Admin Dashboard Needs
- Pairing tracker (who is matched with whom)
- Meeting log (are pairs actually meeting?)
- Goal progress (are mentees hitting milestones?)
- Satisfaction scores (mid-program and final)
- Intervention flags (pairs that miss 2+ meetings)
```

### 2. Mentor Training

Provide mentors with:
- How to ask powerful questions instead of giving advice
- Active listening techniques
- How to hold mentees accountable without being pushy
- When and how to escalate if a mentee needs different support

### 3. Program Health Metrics

```
## Track These Monthly
- Meeting completion rate (target: 85%+)
- Goal progress per pair (on track / behind / ahead)
- Mentor satisfaction score (target: 4+/5)
- Mentee satisfaction score (target: 4+/5)
- Net Promoter Score at program close (target: 50+)
```

---

## Example 1: Business Growth Mentorship (3 Months)

```
Goal: Help early-stage solopreneurs reach their first $5K month
Matching: Revenue-stage mentors ($10K+/mo) paired with pre-revenue or sub-$2K mentees
Cadence: Bi-weekly 45-min calls + async Slack support
Milestones: Month 1 (offer defined), Month 2 (first sales), Month 3 ($5K target)
```

## Example 2: Community Mentorship Program (Free)

```
Goal: Connect experienced community members with newcomers for 6-week orientation
Matching: Self-select from mentor profiles posted in the community
Cadence: Weekly 30-min calls for 6 weeks
Milestones: Week 2 (goals set), Week 4 (first win), Week 6 (independence plan)
```

---

## Anti-Patterns

- **No matching criteria** — random pairing kills engagement. Match on goals and expertise.
- **No meeting structure** — unstructured calls drift into venting sessions. Provide an agenda.
- **No end date** — open-ended mentorships lose momentum. Set a clear duration with optional renewal.
- **Overloading mentors** — more than 3 mentees per mentor degrades quality. Cap it.
- **No mid-program check-in** — waiting until the end to discover a bad match wastes months.
- **Treating mentors as consultants** — mentorship is guidance, not done-for-you service. Set expectations early.

---

## Recovery

- **Not enough mentors:** Reduce mentee cohort size or increase the mentor-to-mentee ratio to 1:3 with group sessions.
- **Bad match identified:** Have a no-fault rematch process. Offer one rematch per program cycle.
- **Mentee not showing up:** After 2 missed meetings, program admin reaches out. After 3, remove from program.
- **Mentor unsure how to help:** Provide conversation starter cards with questions for common mentee challenges.
- **User has never run a mentorship program:** Start with a 6-week pilot with 5 pairs before scaling.
