Strategy Session

Purpose

Conduct systematic strategic decision-making with:

•Auto-context assembly (research + meetings)
•Rigorous framework application with specific findings
•Concrete scenario analysis and quantitative grounding
•Stakeholder mapping when relevant
•Risk assessment with likelihood/impact ratings
•Structured session artifacts for memo generation

When to Use

Activate when:

•User invokes /strategy:session
•Strategic decision needed
•Multiple options require systematic evaluation

Workflow

1. Define Session Topic

Ask user:

•Topic (competitive-analysis, pricing-strategy, product-strategy, market-positioning, etc.)
•Specific decision question to address
•Time horizon (tactical: 3-6 months, strategic: 12+ months)
•Key stakeholders (optional)

Document:

•Create session folder: /datasets/strategy/sessions/{YYYY}/{MM-DD}_{topic}/
•Initialize session-log.md with metadata

2. Gather Research Context

Invoke: research-gathering skill

Parameters:

•Topic matching session focus
•Exclude expired sources (default)
•Include related topics if relevant

Output to: {session-folder}/context.md

Structure:

markdown

# Research Context

**Session**: [Decision question]
**Date**: [YYYY-MM-DD]
**Topic**: [Topic]

## Research Sources ([N] sources)

### [Source 1 Title]
**Path**: [File path]
**Date**: [Source date]
**Key Insight**: [1-2 sentence insight relevant to decision]
**Citation-ready quote**: "[Verbatim 5-25 word quote]"

[Repeat for each source]

## Evidence Summary

**Key Finding 1**: [Synthesis with citations]
**Key Finding 2**: [Synthesis with citations]

**Quantitative Data**:
- [Metric/benchmark from research]
- [Metric/benchmark from research]

**Research Gaps**: [Note what's missing if relevant to decision]

3. Synthesize Meeting Context

Invoke: meeting-synthesis skill

Parameters:

•Time window: 90 days (broader for strategy)
•Topic keywords (from decision question)
•Customer/stakeholder filter if relevant

Append to: {session-folder}/context.md

Add section:

markdown

## Customer/Stakeholder Signals ([N] meetings)

### [Signal 1]
**Source**: [Meeting date, participants]
**Context**: [What was discussed]
**Quote**: "[Verbatim customer/stakeholder quote]"
**Implication**: [How this informs decision]

[Repeat for each significant signal]

## Pattern Summary

**Cross-customer pattern 1**: [What multiple customers said]
**Cross-customer pattern 2**: [What multiple customers said]

**Stakeholder concerns**: [Concerns raised]

4. Select Decision Framework

Framework options based on decision type:

Competitive Analysis:

•Porter's Five Forces (industry structure analysis)
•Competitive Positioning Matrix (relative positioning)
•SWOT Analysis (strengths/weaknesses/opportunities/threats)

Product Strategy:

•Jobs-to-be-Done (customer need mapping)
•Opportunity Solution Tree (problem-solution alignment)
•RICE Prioritization (reach/impact/confidence/effort)
•Product-Market Fit Canvas

Pricing Strategy:

•Value-Based Pricing Framework
•Price Elasticity Analysis
•Competitive Pricing Analysis
•Cost-Plus vs. Value Pricing Trade-offs

Market Positioning:

•Segmentation-Targeting-Positioning (STP)
•Positioning Canvas
•Perceptual Mapping

Organizational/Stakeholder:

•Stakeholder Mapping (power/interest grid)
•RACI Matrix (responsibility assignment)
•Change Impact Analysis

Ask user: "Which framework fits this decision best? [List 2-3 most relevant]"

If user unsure: Recommend based on decision type and explain why

5. Apply Framework Rigorously

Output to: {session-folder}/framework.md

General structure:

markdown

# Framework Analysis

**Framework**: [Framework name]
**Decision**: [Decision question]
**Date**: [YYYY-MM-DD]

## Framework Overview

[Brief description of framework and why it's appropriate for this decision]

## [Framework-Specific Components]

[Use framework structure below based on selection]

## Key Findings from Framework

**Finding 1**: [Specific insight with evidence from context]
**Finding 2**: [Specific insight with evidence from context]

**Quantitative Insights** (if applicable):
- [Metric/comparison from framework application]
- [Metric/comparison from framework application]

## Decision Implications

[What this framework analysis means for the decision at hand]

Porter's Five Forces Template

markdown

## Porter's Five Forces Analysis

### 1. Supplier Power
**Rating**: [LOW | MEDIUM | HIGH]
**Factors**:
- [Factor with evidence]
- [Factor with evidence]
**Implication**: [How this affects decision]

### 2. Buyer Power
**Rating**: [LOW | MEDIUM | HIGH]
**Factors**:
- [Factor with evidence]
- [Factor with evidence]
**Implication**: [How this affects decision]

### 3. Competitive Rivalry
**Rating**: [LOW | MEDIUM | HIGH]
**Factors**:
- [Factor with evidence]
- [Factor with evidence]
**Key competitors**: [List with specific comparison]
**Implication**: [How this affects decision]

### 4. Threat of Substitution
**Rating**: [LOW | MEDIUM | HIGH]
**Alternatives**:
- [Alternative with adoption barrier]
- [Alternative with adoption barrier]
**Implication**: [How this affects decision]

### 5. Threat of New Entrants
**Rating**: [LOW | MEDIUM | HIGH]
**Barriers to Entry**:
- [Barrier]
- [Barrier]
**Implication**: [How this affects decision]

## Overall Industry Attractiveness
[Synthesis: Is this an attractive market/position? Why/why not?]

Stakeholder Mapping Template

markdown

## Stakeholder Analysis

| Stakeholder | Power | Interest | Current Stance | Strategy |
|-------------|-------|----------|----------------|----------|
| [Name/Group] | [H/M/L] | [H/M/L] | [Support/Neutral/Oppose] | [Engage/Monitor/Inform] |

### High Power, High Interest (Manage Closely)
[Stakeholder]: [Specific concerns and engagement strategy]

### High Power, Low Interest (Keep Satisfied)
[Stakeholder]: [Specific concerns and engagement strategy]

### Low Power, High Interest (Keep Informed)
[Stakeholder]: [Specific concerns and engagement strategy]

### Low Power, Low Interest (Monitor)
[Stakeholder]: [Monitoring approach]

## Decision Impact by Stakeholder
[How this decision affects each key stakeholder group]

Pricing Framework Template

markdown

## Value-Based Pricing Analysis

### Customer Value Assessment
**Value Metric**: [What customers get]
**Quantified Value**: [$ or % improvement from research/customer data]
**Value Drivers**:
- [Driver 1 with evidence]
- [Driver 2 with evidence]

### Competitive Pricing Context
| Competitor | Price | Positioning | Value Gap |
|------------|-------|-------------|-----------|
| [Name] | [Price] | [How positioned] | [Relative value] |

### Cost Structure
**Variable Costs**: [Per unit/per customer if known]
**Fixed Costs**: [Relevant fixed costs]
**Target Margin**: [If defined]

### Price Elasticity Considerations
**Elasticity estimate**: [HIGH/MEDIUM/LOW based on evidence]
**Evidence**: [Customer signals, competitive responses, research]

### Pricing Scenarios
[See section 6 for scenario development]

6. Develop Concrete Scenarios

Interactive with user - document in: {session-folder}/session-log.md

Scenario Analysis Structure:

markdown

## Option Analysis

### Option 1: [Descriptive Name]

**Description**: [What this option entails specifically]

**Concrete Scenario**: [Walk through specific example]
- **Example**: [E.g., "Agency with 15 DTC brand clients, average $50k MRR"]
- **Impact**: [What happens in this scenario]
- **Numbers**: [Quantitative impact if estimable]

**Pros**:
- [Advantage with evidence source - be specific]
- [Advantage with evidence source - be specific]

**Cons**:
- [Disadvantage or risk - be specific]
- [Disadvantage or risk - be specific]

**Expected Impact** (quantitative where possible):
- [Metric]: [Expected change with confidence level]
- [Metric]: [Expected change with confidence level]

**Risk Assessment**:
- **Likelihood of success**: [HIGH/MEDIUM/LOW - why?]
- **Impact if fails**: [HIGH/MEDIUM/LOW - what happens?]
- **Reversibility**: [Can we reverse this decision? At what cost?]

**Framework alignment**: [How framework analysis supports/contradicts this option]

[Repeat for each option - aim for 2-4 options]

Scenario depth guidelines:

•Use concrete customer examples from meetings
•Include quantitative estimates (with confidence levels)
•Show trade-offs with specific numbers
•Reference framework findings in analysis
•Note stakeholder impacts per option

7. Facilitate Trade-off Analysis

Add to session-log.md:

markdown

## Trade-off Analysis

| Dimension | Option 1 | Option 2 | Option 3 | Winner |
|-----------|----------|----------|----------|--------|
| [Criterion 1] | [Rating/score] | [Rating/score] | [Rating/score] | [Option] |
| [Criterion 2] | [Rating/score] | [Rating/score] | [Rating/score] | [Option] |

**Key Trade-offs**:
- **[Dimension 1] vs. [Dimension 2]**: [Analysis of trade-off]
- **[Dimension 3] vs. [Dimension 4]**: [Analysis of trade-off]

**Decision Criteria Weighting** (if user provides):
- [Criterion]: [Weight/importance]
- [Criterion]: [Weight/importance]

8. Develop Recommendation

Interactive - capture in: {session-folder}/recommendations.md

markdown

# Recommendations

**Session**: [Decision question]
**Date**: [YYYY-MM-DD]

## Recommendation

**We recommend: Option [N] - [Name]**

## Rationale

1. **[Reason 1]**: [Detailed explanation with evidence]
   - Framework support: [How framework analysis supports]
   - Evidence: [Citations from research/meetings]
   - Quantitative basis: [Numbers if available]

2. **[Reason 2]**: [Detailed explanation with evidence]
   - Framework support: [How framework analysis supports]
   - Evidence: [Citations from research/meetings]
   - Quantitative basis: [Numbers if available]

3. **[Reason 3]**: [Detailed explanation with evidence]
   - Framework support: [How framework analysis supports]
   - Evidence: [Citations from research/meetings]
   - Quantitative basis: [Numbers if available]

## Expected Outcomes

**Primary Outcomes**:
- [Outcome 1 with metric and timeframe]
- [Outcome 2 with metric and timeframe]

**Secondary Outcomes**:
- [Outcome 3]
- [Outcome 4]

## Success Metrics

**Must be specific and measurable:**

| Metric | Baseline | Target | Timeline | Measurement Method |
|--------|----------|--------|----------|-------------------|
| [Metric 1] | [Current] | [Target] | [When] | [How to measure] |
| [Metric 2] | [Current] | [Target] | [When] | [How to measure] |

**Review Cadence**: [When to assess progress]

## Risk Management

### Risk 1: [Description]
- **Likelihood**: [LOW/MEDIUM/HIGH]
- **Impact**: [LOW/MEDIUM/HIGH]
- **Mitigation**: [Specific strategy]
- **Trigger/Threshold**: [When to escalate or pivot - if applicable]
- **Contingency**: [What to do if risk materializes]

[Repeat for each significant risk - aim for 3-5 risks]

## Key Dependencies

**Internal Dependencies**:
- [Dependency 1 - what needs to happen]
- [Dependency 2 - what needs to happen]

**External Dependencies**:
- [Dependency 3 - outside our control]
- [Dependency 4 - outside our control]

## Decision Gates (If Applicable)

[Critical decision points where we pause and reassess]

**Gate 1** ([Timeframe]): [What we assess and decision to make]
**Gate 2** ([Timeframe]): [What we assess and decision to make]

## Implementation Considerations (High-Level)

[Strategic guidance only - NOT project plan]

**Critical path items**: [What must happen in what order]
**Resource requirements**: [High-level resource needs]
**Timeline**: [Strategic phases - high-level only]

**Note**: Detailed implementation planning should be separate project management work.

9. Offer Memo Generation

Ask user: "Generate formal strategy memo from this session?"

If yes:

•Announce: "I'm using strategy-memo to create formal documentation"
•Invoke: strategy-memo skill
•Provide session folder path

If no:

•Confirm session artifacts saved
•Note memo can be generated later with /strategy:memo

Session Quality Checklist

Before marking session complete:

Quality flags - need more work if:

•Vague recommendations without concrete action
•Missing quantitative grounding for quantifiable decisions
•Options lack concrete scenarios or examples
•Framework applied superficially without specific findings
•Success metrics not measurable or no timeline
•Risks identified without mitigation strategies
•Unsupported projections or speculation

File Structure

Session folder: /datasets/strategy/sessions/{YYYY}/{MM-DD}_{topic}/

Required files:

•context.md - Research and meeting context
•framework.md - Framework application and findings
•session-log.md - Interactive discussion and option analysis
•recommendations.md - Final recommendation with rationale

Optional files:

•scenarios.md - If extensive scenario modeling
•stakeholders.md - If detailed stakeholder analysis
•data.csv or analysis.xlsx - If quantitative modeling

Success Criteria

•Context systematically assembled from research and meetings
•Framework applied rigorously with specific findings
•Options analyzed with concrete scenarios
•Quantitative data included where decision benefits from it
•Trade-offs analyzed explicitly
•Recommendation backed by framework and evidence
•Success metrics measurable with timelines
•Risk assessment includes likelihood/impact
•All artifacts ready for memo generation
•Session documented to enable future reference

Related Skills

•research-gathering: Assembles research context
•meeting-synthesis: Provides customer evidence
•strategy-memo: Generates formal memo from session
•citation-compliance: Used in memo for validation