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:

# Analyze survey data
uv run skills/strategic-planning-manager/scripts/analyze_surveys.py \
  --input survey_results.csv \
  --output-dir ./discovery

# Process focus group transcripts
uv run skills/strategic-planning-manager/scripts/process_transcripts.py \
  --input-dir ./transcripts \
  --output ./discovery/transcript-themes.json

# Generate SWOT from discovery data
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:

# Generate strategic plan document from all stage outputs
uv run skills/strategic-planning-manager/scripts/synthesize_plan.py \
  --work-dir ./planning \
  --output ./outputs/strategic-plan.md \
  --format full  # or 'executive', 'board', 'staff', 'community'

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  # or 'executive', 'board', 'staff', 'community'

Generates:

• Complete strategic plan document
• Multiple stakeholder versions
• Executive summary
• Board presentation outline

Facilitator Guides

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:

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