| name | strategic-planning-manager |
| description | Organizational strategic planning for K-12 school districts using a research-backed 4-stage process |
| triggers | ["strategic planning","district strategic plan","k-12 strategic planning","school district planning","strategic plan","SWOT analysis","strategic directions","strategic retreat","organizational planning"] |
| keep-coding-instructions | true |
| allowed-tools | ["Read","Write","Bash","Edit","Glob","Grep","AskUserQuestion","WebSearch","mcp__obsidian-vault__create_vault_file","mcp__obsidian-vault__get_vault_file","mcp__obsidian-vault__search_vault_simple"] |
| version | 2.0.0 |
Strategic Planning Manager Skill
Organizational strategic planning system for K-12 school districts using a research-backed 4-stage process. Synthesizes best practices from Education Elements, Hanover Research, AASA, ThoughtExchange, and facilitation methodology.
Start Here: New to this skill? Read guides/leader-overview.md for a full introduction to the 4-stage process, superintendent roles, team formation, and readiness assessment.
Note: For personal life/work strategic planning, use the personal-strategic-planning skill instead.
When to Activate
This skill activates when the user requests:
Full Strategic Planning Process:
- "Help me create a strategic plan for our district"
- "We need to do strategic planning"
- "Let's start the district strategic planning process"
- "Facilitate our strategic planning retreat"
Stage-Specific Work:
- "Analyze our survey data for strategic planning"
- "Help me process focus group transcripts"
- "Generate a SWOT analysis"
- "Help define our strategic directions"
- "Build our implementation timeline"
- "Set up progress monitoring"
Plan Update Mode:
- "Update our existing strategic plan"
- "It's time to refresh our strategic plan"
- "Annual strategic plan review"
Skill Modes
Mode 1: Full Process Guide
Walk through all 4 stages sequentially, prompting for data inputs and facilitating each step.
- Best for: New strategic plans, comprehensive planning retreats
Mode 2: Stage-Specific Entry
Jump directly into any specific stage with appropriate inputs.
- Best for: Working on one component, picking up where you left off
Mode 3: Data Analysis Only
Process surveys, transcripts, and documents without running the full planning process.
- Best for: Pre-work, discovery, feeding data into existing processes
Mode 4: Plan Update
Start from an existing plan, analyze progress, update for a new cycle.
- Best for: Annual reviews, mid-cycle adjustments, refresh cycles
The 4-Stage Strategic Planning Process
Stage 1: Engage & Assess
Key Question: Where are we now?
AI Role: Data analysis, synthesis, draft preparation
Human Role: Data collection, stakeholder engagement, validation
What Happens:
- Gather and analyze data (surveys, focus groups, document review)
- Engage stakeholders across the community
- Conduct SWOT analysis with prioritization
- Identify investment opportunities and critical barriers
Available Scripts:
uv run skills/strategic-planning-manager/scripts/analyze_surveys.py \
--input survey_results.csv \
--output-dir ./discovery
uv run skills/strategic-planning-manager/scripts/process_transcripts.py \
--input-dir ./transcripts \
--output ./discovery/transcript-themes.json
uv run skills/strategic-planning-manager/scripts/generate_swot.py \
--discovery-dir ./discovery \
--output ./outputs/swot-analysis.md
Outputs:
- Discovery Report (
templates/discovery-report.md)
- SWOT Analysis (
templates/swot-template.md)
- Stakeholder input summary
- Key findings synthesis
Guide: guides/stage1-engage-assess-guide.md
Stage 2: Set Direction
Key Question: Where do we want to go?
AI Role: Provide prompts, capture input, map alignment
Human Role: Visioning, decision-making, prioritization
What Happens:
- Define or reaffirm Mission, Vision, and Values
- Identify 3-6 district priority areas
- Define long-term outcome goals
- Develop 4-6 strategic directions
Optional Deeper Work:
- Deep participatory visioning exercise →
guides/appendix-a-vision-development.md
- Organizational tension analysis →
guides/appendix-b-tension-analysis.md
- Developing a Profile of a Graduate →
guides/appendix-c-graduate-profile.md
Outputs:
- Mission/Vision/Values statements
- Priority areas with outcome goals
- Strategic Directions Framework (
templates/strategic-directions.md)
- Direction-to-priority alignment matrix
Guide: guides/stage2-set-direction-guide.md
Stage 3: Build the Plan & Align Resources
Key Question: How will we get there?
AI Role: Structure creation, timeline drafting, metric suggestions
Human Role: Reality testing, commitment making, ownership assignment
What Happens:
- Develop three-column plans (Current Reality → 1-Year → 3-Year)
- Define measurable goals and success indicators
- Choose strategies/initiatives per direction
- Assign ownership and align resources
- Build Year 1 quarterly timeline
- Cross-direction integration check
Outputs:
- Implementation Tables (
templates/focused-implementation.md)
- Success indicator matrix
- First-Year Timeline (
templates/first-year-timeline.md)
- Resource alignment plan
- Ownership chart
Guide: guides/stage3-build-plan-guide.md
Stage 4: Implement, Monitor & Improve
Key Question: Are we making progress?
AI Role: Dashboard creation, report drafting, data analysis
Human Role: Implementation leadership, decision-making, accountability
What Happens:
- Develop annual action plans
- Track leading and lagging indicators
- Report to board and community on regular cadence
- Make mid-course adjustments when data warrants
- Conduct annual reviews and mid-plan refreshes
Available Scripts:
uv run skills/strategic-planning-manager/scripts/synthesize_plan.py \
--work-dir ./planning \
--output ./outputs/strategic-plan.md \
--format full
Outputs:
- Full Strategic Plan Document (
templates/full-strategic-plan.md)
- Executive Summary (
templates/executive-summary.md)
- Annual action plans
- Progress dashboards
- Board reports
Guide: guides/stage4-implement-improve-guide.md
Available Scripts
Survey Analysis
uv run skills/strategic-planning-manager/scripts/analyze_surveys.py \
--input data.csv \
--format csv \
--output-dir ./discovery
Supported formats: CSV, JSON, Excel (.xlsx, .xls)
Analysis includes:
- Response distribution statistics
- Sentiment analysis per question
- Theme extraction from open-ended responses
- Stakeholder group comparisons (if demographics provided)
- Word frequency and phrase analysis
Transcript Processing
uv run skills/strategic-planning-manager/scripts/process_transcripts.py \
--input-dir ./transcripts \
--output ./discovery/transcript-themes.json
Analysis includes:
- Theme extraction using NLP
- Sentiment patterns
- Speaker/stakeholder attribution (if labeled)
- Quote extraction for evidence
- Cross-transcript pattern identification
SWOT Generation
uv run skills/strategic-planning-manager/scripts/generate_swot.py \
--discovery-dir ./discovery \
--output ./outputs/swot-analysis.md
Generates:
- Data-driven SWOT matrix
- Supporting evidence citations
- Investment priority recommendations
- Barrier analysis
Plan Synthesis
uv run skills/strategic-planning-manager/scripts/synthesize_plan.py \
--work-dir ./planning \
--output ./outputs/strategic-plan.md \
--format full
Generates:
- Complete strategic plan document
- Multiple stakeholder versions
- Executive summary
- Board presentation outline
Facilitator Guides
| Guide | Purpose | Duration |
|---|
leader-overview.md | Full process overview for superintendents | Reference |
stage1-engage-assess-guide.md | Data collection + SWOT workshop | 2-6 weeks + 2.5 hrs |
stage2-set-direction-guide.md | Vision, priorities, strategic directions | 3-4 hours |
stage3-build-plan-guide.md | Implementation planning workshop | 3-4 hours |
stage4-implement-improve-guide.md | Monitoring and continuous improvement | Ongoing |
appendix-a-vision-development.md | Deep participatory visioning exercise | 3-4 hours |
appendix-b-tension-analysis.md | Organizational tension analysis | 2-3 hours |
appendix-c-graduate-profile.md | Profile of a Graduate development process | Multi-session |
six-month-timeline.md | Month-by-month planning timeline | Reference |
retreat-agenda-2day.md | Full 2-day retreat (all 4 stages) | 2 days |
retreat-agenda-condensed.md | Condensed 1-day (Stages 1-3) | 1 day |
Each guide includes:
- Detailed agenda with timing
- Facilitator prompts and questions
- Small group and large group activities
- Materials needed
- Expected outputs
- Common challenges and solutions
Data Storage (Obsidian)
Strategic plans are stored in the Obsidian vault:
Personal_Notes/Geoffrey/Strategic-Plans/
├── {District-Name}/
│ ├── {Year}-Strategic-Plan.md
│ ├── Discovery-Report.md
│ ├── SWOT-Analysis.md
│ ├── Strategic-Directions.md
│ ├── Implementation-Plan.md
│ ├── Progress-Reports/
│ │ └── [Quarterly/annual reports]
│ └── Facilitator-Guides/
│ └── [Generated guides for this district]
Frontmatter:
---
type: strategic-plan
district: {District Name}
year: {YYYY}
stage: {1-4 or complete}
status: draft | in-progress | final
created: {date}
updated: {date}
---
Common K-12 Strategic Themes
Pre-loaded from config/k12-themes.yaml:
| Theme | Prevalence | Key Metrics |
|---|
| Student Achievement | 90%+ | Test scores, graduation rates, college readiness |
| Equity & Access | 90% | Gap reduction, program access, representation |
| Staff Quality & Retention | 80% | Hiring, development, turnover rates |
| Parent/Community Engagement | 80% | Participation, satisfaction, partnerships |
| Facilities & Technology | 75% | Infrastructure, device ratios, connectivity |
| Fiscal Sustainability | 70% | Budget balance, reserves, cost efficiency |
| Social-Emotional Learning | Growing | SEL metrics, climate surveys, wellness |
| Safety & Security | Variable | Incident rates, preparedness, climate |
Research Foundations
This skill synthesizes best practices from:
ThoughtExchange 3 Models:
- Plan on a Page
- VMOSA (Vision → Mission → Objectives → Strategies → Action Plan)
- Five-Step Model
Education Elements (7 Steps):
- Pre-Planning Assessment
- Community Engagement Strategy
- Strategic Planning Team Formation
- Build Common Understanding
- Design Solutions (prioritization matrix)
- Communication Planning
- Monitoring and Adaptation
Hanover Research (5 Phases):
- Discovery (surveys, benchmarking)
- Analysis (SWOT synthesis)
- Visioning (workshops)
- Goal Setting (SMART goals)
- Implementation Roadmap (KPIs)
AASA 10-Step Framework:
- Comprehensive district leadership approach
- Emphasis on board/superintendent buy-in
- Quarterly monitoring, annual evaluation
Facilitation Methodology:
- ORID Method (Objective → Reflective → Interpretive → Decisional)
- Focused Conversation
- Consensus Workshop
- Strategic Planning Matrix
Example Workflow
Starting a New Strategic Plan
User: "Help me create a strategic plan for our district"
Geoffrey:
1. Ask which mode: Full Process, Stage-Specific, or Data Analysis
2. If Full Process:
- Ask about available data (surveys, transcripts, existing docs)
- Ask about timeline (retreat dates, board presentation date)
- Ask about stakeholder groups to involve
3. Begin Stage 1: Engage & Assess
- Ingest provided data files
- Generate Discovery Report and SWOT
4. Continue through stages with appropriate AI/human balance
5. Generate final plan documents
6. Save to Obsidian vault
Analyzing Survey Data Only
User: "I have survey results I need to analyze for strategic planning"
Geoffrey:
1. Ask for data file(s) and format
2. Run analyze_surveys.py
3. Present findings:
- Key themes
- Stakeholder differences
- Sentiment analysis
- Suggested SWOT inputs
4. Ask if user wants to continue to SWOT generation
Updating an Existing Plan
User: "We need to update our strategic plan for year 2"
Geoffrey:
1. Load existing plan from Obsidian
2. Ask about progress on Year 1 accomplishments
3. Collect new data/feedback
4. Identify what's on track, at risk, off track
5. Recommend adjustments to timeline/directions
6. Generate updated plan document
Error Handling
1. No data provided for discovery:
- Offer to conduct discovery interviews directly
- Suggest data collection templates
- Proceed with qualitative input only
2. Insufficient stakeholder representation:
- Flag which groups are missing
- Recommend targeted data collection
- Note limitation in final report
3. Conflicting stakeholder priorities:
- Surface tensions explicitly
- Use as input for strategic direction decisions
- Document minority viewpoints
4. Unrealistic implementation timeline:
- Flag capacity concerns
- Suggest prioritization/phasing
- Recommend reducing scope or extending timeline
5. Plan update with no progress data:
- Conduct progress interview
- Use qualitative assessment
- Note "self-reported" vs "measured" progress
Version History
v2.0.1 (2026-02-02)
- Added Appendix C: Developing a Profile of a Graduate
- Community workshop and student voice facilitation scripts
- Common competency categories reference table
- Guidance on connecting profile to strategic plan
- Updated facilitation prompts with graduate_profile section
v2.0.0 (2026-02-02)
- Restructured from 7-phase to 4-stage process
- 4 stages: Engage & Assess → Set Direction → Plan & Align → Implement & Improve
- New leader overview with readiness self-assessment
- New Stage 4 guide (monitoring, board reporting, review cycles)
- New 6-month planning timeline
- New fillable strategic planning template
- Deep visioning moved to Appendix A
- Tension analysis moved to Appendix B (rebranded from "contradictions")
- Retreat agendas restructured around 4 stages
- Removed methodology-specific branding throughout
v1.0.0 (2026-01-26)
- Initial release
- 7-phase methodology
- 4 skill modes (Full, Phase-Specific, Data Analysis, Update)
- Python scripts for data analysis
- Facilitator guides for human sessions
- Obsidian integration for plan storage
- K-12 themes and metrics library
- Research-backed framework synthesis
