fatby/strategic-planning

Strategic Planning Skill

A comprehensive framework for long-term strategic thinking, scenario planning, and roadmap development.

When to Use This Skill

1. Business strategy development
2. Product roadmap creation
3. Career planning and development
4. Multi-phase project planning
5. Competitive positioning analysis
6. Resource allocation decisions
7. Scenario planning for uncertainty

The Strategic Planning Framework

Phase 1: Vision & Purpose

Define the ultimate goal and why it matters:

1. Aspirational Vision: Where do we want to be in 3-5 years?
2. Core Purpose: Why does this matter fundamentally?
3. Guiding Principles: What values will guide decisions?
4. Success Metrics: How will we know we've succeeded?

Phase 2: Situation Analysis

Understand the current reality:

Internal Analysis:

• Strengths: What do we do exceptionally well?
• Weaknesses: Where do we need improvement?
• Capabilities: What skills, resources do we have?
• Constraints: What limits our options?

External Analysis:

• Opportunities: What trends could we leverage?
• Threats: What challenges could derail us?
• Competitive Landscape: Who competes and how?
• Market Trends: What's changing in the environment?

Phase 3: Strategic Options Generation

Create multiple paths to the vision:

1. Option A: Conservative/evolutionary approach
2. Option B: Bold/revolutionary approach
3. Option C: Hybrid/balanced approach
4. Option D: Experimental/pilot approach

Each option includes:

• Core thesis
• Key assumptions
• Resource requirements
• Risk profile
• Time horizon

Phase 4: Scenario Planning

Prepare for different futures:

| Scenario | Probability | Description | Preparedness | |----------|-------------|-------------|--------------| | Base Case | 50% | Expected trajectory | Primary plan | | Upside Case | 25% | Better than expected | Opportunity capture | | Downside Case | 20% | Challenges emerge | Risk mitigation | | Black Swan | 5% | Unexpected disruption | Resilience plans |

Phase 5: Roadmapping

Translate strategy to actionable plan:

Time Horizons:

• Now (0-3 months): Immediate priorities
• Next (3-12 months): Short-term initiatives
• Later (1-3 years): Medium-term projects
• Future (3-5 years): Long-term vision

Initiative Structure:

• Objective: What we want to achieve
• Key Results: Measurable outcomes
• Initiatives: Projects to achieve results
• Owners: Who's responsible
• Timeline: When it happens
• Resources: What's needed

Phase 6: Execution & Adaptation

Monitor and adjust:

1. Key Performance Indicators (KPIs): Track progress
2. Leading Indicators: Early warning signals
3. Review Cadence: Regular strategy reviews
4. Adaptation Triggers: When to change course
5. Learning Loops: Capture insights for improvement

Application Templates

Strategic Plan Template

# Strategic Plan: [Initiative Name]

## 1. Vision & Purpose
- **Aspirational Vision**: 
- **Core Purpose**: 
- **Guiding Principles**: 
- **Success Metrics**: 

## 2. Situation Analysis
### Internal
- Strengths: 
- Weaknesses: 
- Capabilities: 
- Constraints: 

### External
- Opportunities: 
- Threats: 
- Competition: 
- Trends: 

## 3. Strategic Options
### Option A: [Name]
- Thesis: 
- Key Assumptions: 
- Resources: 
- Risks: 
- Timeline: 

### Option B: [Name]
- Thesis: 
- Key Assumptions: 
- Resources: 
- Risks: 
- Timeline: 

## 4. Scenario Planning
### Base Case (50%)
- Description: 
- Preparedness: 

### Upside Case (25%)
- Description: 
- Opportunity Capture: 

### Downside Case (20%)
- Description: 
- Risk Mitigation: 

### Black Swan (5%)
- Description: 
- Resilience Plan: 

## 5. Roadmap
### Now (0-3 months)
- Initiatives: 
- Owners: 
- Success Metrics: 

### Next (3-12 months)
- Initiatives: 
- Owners: 
- Success Metrics: 

### Later (1-3 years)
- Initiatives: 
- Owners: 
- Success Metrics: 

### Future (3-5 years)
- Vision Realization: 

## 6. Execution
- KPIs: 
- Leading Indicators: 
- Review Cadence: 
- Adaptation Triggers: 

Product Roadmap Template

# Product Roadmap: [Product Name]

## Vision
[Where we want the product to be in 3 years]

## Themes & Objectives
### Theme 1: [e.g., User Experience]
- Objective: 
- Key Results: 
- Initiatives: 
  - [Q1] Initiative A
  - [Q2] Initiative B

### Theme 2: [e.g., Platform Stability]
- Objective: 
- Key Results: 
- Initiatives: 
  - [Q1] Initiative C
  - [Q2] Initiative D

## Timeline View
### Q1 2026
- [ ] Initiative A (Theme 1)
- [ ] Initiative C (Theme 2)

### Q2 2026
- [ ] Initiative B (Theme 1)
- [ ] Initiative D (Theme 2)

## Success Metrics
- User Engagement: 
- Revenue Impact: 
- Technical Health: 
- Customer Satisfaction: 

Strategic Thinking Tools

SWOT Analysis

          Helpful      Harmful
Internal  Strengths    Weaknesses
External  Opportunities Threats

Porter's Five Forces

1. Competitive Rivalry: Intensity of competition
2. Supplier Power: Supplier bargaining power
3. Buyer Power: Customer bargaining power
4. Threat of Substitution: Alternative solutions
5. Threat of New Entry: New competitors

Ansoff Matrix

         Existing Products  New Products
Existing  Market Penetration  Product Development
Markets   (Increase share)    (New products for current customers)
New       Market Development  Diversification
Markets   (New markets for    (New products for new markets)
          current products)

BCG Growth-Share Matrix

• Stars: High growth, high share (invest)
• Cash Cows: Low growth, high share (milk)
• Question Marks: High growth, low share (analyze)
• Dogs: Low growth, low share (divest)

Integration with Other Skills

With Structured Reasoning

Use strategic planning as the high-level context:

1. Framing: Strategic objectives
2. Options: Strategic alternatives
3. Validation: Strategic fit assessment

With Critical Evaluation

Apply critical thinking to strategic assumptions:

• Challenge market assumptions
• Identify strategic biases
• Test scenario probabilities

With Proactive Agent

Enable proactive strategic initiatives:

• Market monitoring
• Competitive intelligence
• Opportunity identification

Examples

Example 1: Startup Growth Strategy

Situation: "How should we grow our SaaS startup?" Strategic Planning:

1. Vision: Become #1 in SMB CRM within 3 years
2. Analysis: Strong product (strength), Limited sales (weakness), Market growing 30% annually (opportunity)
3. Options:
   • Option A: Aggressive sales hiring
   • Option B: Channel partnerships
   • Option C: Product-led growth
4. Scenarios:
   • Base: 30% growth
   • Upside: 50% growth with viral adoption
   • Downside: 15% growth with churn issues
5. Roadmap:
   • Now: Fix onboarding
   • Next: Add integrations
   • Later: Enterprise features
6. Execution: Weekly growth metrics, monthly strategy review

Example 2: Career Transition

Situation: "Planning transition from engineering to product management" Strategic Planning:

1. Vision: Senior PM role at tech company within 2 years
2. Analysis: Technical background (strength), No PM experience (weakness), High demand for technical PMs (opportunity)
3. Options:
   • Option A: Internal transition at current company
   • Option B: MBA then PM role
   • Option C: Side projects to build portfolio
4. Roadmap:
   • Q1: Learn PM fundamentals
   • Q2: Lead small project
   • Q3: Formal PM application
   • Q4: Transition complete
5. Success Metrics: PM interviews, project success, salary target

Implementation Guidance

Time Allocation by Role

| Role | Strategic Time | Operational Time | |------|---------------|------------------| | Executive | 60-70% | 30-40% | | Manager | 30-40% | 60-70% | | Individual Contributor | 10-20% | 80-90% |

Common Pitfalls to Avoid

1. Analysis Paralysis: Over-analyzing, under-acting
2. Strategy/Execution Gap: Beautiful plan, poor implementation
3. Annual Ritual: Strategy as yearly event, not daily practice
4. Ivory Tower: Strategy divorced from reality
5. Resource Starvation: Strategy without resources

Success Indicators

1. Clear Priorities: Team knows what matters
2. Aligned Actions: Daily work connects to strategy
3. Adaptive: Course corrections when needed
4. Measurable Progress: Can track toward goals
5. Engaged Team: Understands and believes in strategy

Tool Integration

For Analysis

• web_search: Market research, competitor analysis
• memory_search: Past strategic decisions, lessons learned
• read_file: Existing plans, performance data

For Planning

• write_file: Document strategic plans
• append_file: Update roadmaps
• list_dir: Review existing initiatives

For Execution

• run_cmd: Automation scripts
• sessions_spawn: Strategic working groups
• search_codebase: Technical capabilities assessment

Continuous Improvement

Strategic Review Questions

1. What assumptions proved wrong?
2. What unexpected opportunities emerged?
3. What execution challenges appeared?
4. What metrics were most predictive?
5. How should we adjust our strategy?

Learning Capture

• Successful strategic patterns
• Failed assumptions and why
• Effective adaptation methods
• Team alignment techniques

References

• Collins, J. (2001). Good to Great
• Christensen, C. (1997). The Innovator's Dilemma
• Rumelt, R. (2011). Good Strategy/Bad Strategy
• Osterwalder, A. (2010). Business Model Generation