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SKILL.md

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name product-strategy-session
description Facilitate a complete product strategy session — positioning, problem framing, solution exploration, prioritization, stakeholder alignment, and execution planning — over 2-4 weeks.
type workflow
domain strategy
difficulty advanced
estimated_time 2-4 weeks
prerequisites
outputs
strategy-document
roadmap
stakeholder-presentation
triggers
Run a product strategy session
Align stakeholders on product strategy
Full strategy planning
Complete product strategy exercise

Purpose

Orchestrate a complete product strategy session from positioning through execution planning. This workflow sequences 12+ skills across 6 phases, typically over 2-4 weeks, to align the team on what to build, for whom, and why.

Application

Phase 1: Positioning & Market Context (Week 1, Days 1-2)

Goal: Define target customer, problem space, and differentiation.

Activity Skill Time
Define positioning skills/strategy/positioning-workshop/SKILL.md 60 min
Create proto-personas skills/discovery/proto-persona/SKILL.md 45 min
Map jobs-to-be-done skills/discovery/jobs-to-be-done/SKILL.md 45 min
Run PESTEL analysis skills/strategy/pestel-analysis/SKILL.md 30 min
Run SWOT analysis skills/strategy/swot-analysis/SKILL.md 25 min

Decision Point 1: Do we have enough customer context?

  • ✅ YES → Proceed to Phase 2
  • ❌ NO → Schedule discovery interviews (+1 week)

Phase 2: Problem Framing & Validation (Week 1, Days 3-5)

Activity Skill Time
Frame the problem skills/discovery/problem-framing-canvas/SKILL.md 60 min
Write problem statement skills/discovery/problem-statement/SKILL.md 30 min
Map customer journey skills/discovery/customer-journey-mapping-workshop/SKILL.md 60 min

Decision Point 2: Is the problem validated?

  • ✅ YES → Proceed to Phase 3
  • ❌ NO → Run discovery cycle (+1-2 weeks)

Phase 3: Solution Exploration (Week 2, Days 1-3)

Activity Skill Time
Generate opportunity tree skills/specification/opportunity-solution-tree/SKILL.md 60 min
Write epic hypotheses skills/planning/epic-hypothesis/SKILL.md 45 min
Map user stories skills/specification/user-story-mapping-workshop/SKILL.md 90 min

Decision Point 3: Do we need to test solutions before committing?

  • ✅ YES → Design experiments (+1-2 weeks)
  • ❌ NO → Proceed to Phase 4

Phase 4: Prioritization & Roadmap (Week 2, Days 4-5)

Activity Skill Time
Choose framework skills/planning/prioritization-advisor/SKILL.md 30 min
Score and prioritize [Using chosen framework] 60 min
Build roadmap skills/planning/roadmap-planning/SKILL.md 90 min
Define OKRs skills/strategy/okr-framework/SKILL.md 30 min

Phase 5: Stakeholder Alignment (Week 3)

Activity Skill Time
Write press release skills/strategy/press-release/SKILL.md 30 min
Build presentation skills/communication/executive-presentation/SKILL.md 60 min
Map stakeholders skills/communication/stakeholder-map/SKILL.md 20 min
Present and refine [Live session] 60 min

Phase 6: Execution Planning (Week 4)

Activity Skill Time
Break down epics skills/planning/epic-breakdown-advisor/SKILL.md 60 min
Write user stories skills/specification/user-story/SKILL.md 30 min each
Define DoD skills/execution/definition-of-done/SKILL.md 15 min
Plan first sprint skills/execution/sprint-planning-facilitator/SKILL.md 45 min

Complete Workflow Summary

Week 1: POSITION & FRAME
├─ Day 1-2: Market Context
│  ├─ positioning-workshop (60 min)
│  ├─ proto-persona (45 min)
│  ├─ jobs-to-be-done (45 min)
│  ├─ pestel-analysis (30 min)
│  └─ swot-analysis (25 min)
├─ Day 3-5: Problem Validation
│  ├─ problem-framing-canvas (60 min)
│  ├─ problem-statement (30 min)
│  └─ customer-journey-mapping-workshop (60 min)
└─ Decision: Problem validated?

Week 2: EXPLORE & PRIORITIZE
├─ Day 1-3: Solution Exploration
│  ├─ opportunity-solution-tree (60 min)
│  ├─ epic-hypothesis (45 min)
│  └─ user-story-mapping-workshop (90 min)
├─ Day 4-5: Prioritization & Roadmap
│  ├─ prioritization-advisor (30 min)
│  ├─ roadmap-planning (90 min)
│  └─ okr-framework (30 min)
└─ Decision: Need experiments?

Week 3: ALIGN
├─ press-release (30 min)
├─ executive-presentation (60 min)
├─ stakeholder-map (20 min)
└─ Present + refine (60 min)

Week 4: EXECUTE
├─ epic-breakdown-advisor (60 min)
├─ user-story (30 min × N)
├─ definition-of-done (15 min)
└─ First sprint planning (45 min)

Common Pitfalls

Pitfall 1: Skipping Problem Validation

Fix: Strategy without validated problems is strategy theater. Always run Phase 2.

Pitfall 2: Strategy Session Without Executive Sponsorship

Fix: Strategy that leadership doesn't own won't survive contact with reality. Get exec buy-in before Phase 1.

Pitfall 3: Strategy as Permanent Process

Fix: Strategy sessions have an end date. Set timeboxes for each phase and commit to decisions.

References

Skills Orchestrated

All skills in Domains 1-5 can be called upon by this workflow.

External Frameworks

  • Geoffrey Moore, Crossing the Chasm — Positioning
  • Teresa Torres, Continuous Discovery Habits — Problem validation
  • Marty Cagan, Inspired — Product strategy

Skill type: Workflow Domain: Strategy & Vision