Run an end-to-end product strategy session across positioning, discovery, and roadmap planning. Use when a team needs validated direction before committing to execution.

Purpose Guide product managers through a comprehensive product strategy session by orchestrating positioning, problem framing, customer discovery, and roadmap planning skills into a cohesive end to end process. Use this to move from vague strategic direction to concrete, validated product strategy with clear positioning, target customers, problem statements, and prioritized roadmap—ensuring alignment across stakeholders before committing to execution. This is not a one time workshop—it's a repeatable process for establishing or refreshing product strategy, typically spanning 2 4 weeks with multiple touchpoints. Input Works best with: The product (or product line) and the strategic question forcing the session. Also useful: Existing positioning, discovery artifacts, roadmap drafts, and who needs to align on the outcome. Anything supplied with the invocation itself — text after the skill name, a pasted context dump, or an appended ARGUMENTS: line — counts as answers already given. Use it and skip whatever it covers; don't re ask. Arriving empty handed? That works too. The workflow starts at positioning and orchestrates the phases from there — supplied artifacts let it skip ahead. Example invocation: Run a strategy session for our analytics add on: flat adoption, two competing roadmap visions, exec review in 4 weeks. Key Concepts What is a Product Strategy Session? A product strategy session is a structured, multi phase process that takes a product from strategic ambiguity to validated direction. It orchestrates: 1. Positioning & Market Context — Define who you serve, what problem you solve, and how you're differentiated 2. Problem Discovery & Validation — Frame and validate customer problems through research 3. Solution Exploration — Generate opportunity solutions and prioritize based on impact 4. Roadmap Planning — Sequence epics and releases based on strategy Why This Works Structured discovery: Prevents jumping to solutions before understanding problems Stakeholder alignment: Creates shared mental model across exec, product, design, engineering Validated strategy: Tests assumptions before committing resources Executable roadmap: Connects high level strategy to concrete work Anti Patterns (What This Is NOT) Not a feature brainstorm: Strategy sessions frame problems, not just list features Not waterfall planning: Builds in feedback loops and iteration Not a solo PM exercise: Requires cross functional participation When to Use This Launching a new product or major initiative Annual/quarterly strategic planning cycles Repositioning an existing product Onboarding new product leaders (align on strategy) When NOT to Use This When strategy is already clear and validated For tactical feature additions (no strategic shift needed) When you lack executive sponsorship (strategy won't stick) Facilitation Source of Truth When running this workflow as a guided conversation, use [ workshop facilitation ](../workshop facilitation/SKILL.md) as the interaction protocol. It defines: session heads up + entry mode (Guided, Context dump, Best guess) one question turns with plain language prompts progress labels (for example, Context Qx/8 and Scoring Qx/5) interruption handling and pause/resume behavior numbered recommendations at decision points quick select numbered response options for regular questions (include Other (specify) when useful) This file defines the workflow sequence and domain specific outputs. If there is a conflict, follow this file's workflow logic. Application Use template.md for the full fill in structure. This workflow orchestrates 6 phases over 2 4 weeks , using multiple component and interactive skills. Phase 1: Positioning & Market Context (Week 1, Days 1 2) Goal: Define target customer, problem space, and differentiation. Activities 1. Run Positioning Workshop Use: skills/positioning workshop/SKILL.md (interactive) Participants: PM, product leadership, marketing, sales Duration: 90 minutes Output: Draft positioning statement 2. Define Proto Personas Use: skills/proto persona/SKILL.md (component) Participants: PM, design, customer facing teams Duration: 60 minutes Output: 1 3 proto personas (hypothesis driven) 3. Map Jobs to be Done Use: skills/jobs to be done/SKILL.md (component) Participants: PM, design Duration: 60 minutes Output: JTBD statements for each persona Decision Point 1: Do we have enough customer context? If YES: Proceed to Phase 2 (Problem Framing) If NO: Run additional discovery: Use: skills/discovery interview prep/SKILL.md (interactive) Schedule 5 10 customer interviews Validate positioning assumptions before proceeding Time impact: +1 week Phase 2: Problem Framing & Validation (Week 1, Days 3 5) Goal: Frame the core customer problem and validate it's worth solving. Activities 1. Run Problem Framing Canvas Use: skills/problem framing canvas/SKILL.md (interactive MITRE) Participants: PM, design, engineering lead, customer success Duration: 120 minutes Output: Refined problem statement + "How Might We" question 2. Create Formal Problem Statement Use: skills/problem statement/SKILL.md (component) Participants: PM Duration: 30 minutes Output: Structured problem statement for PRD/roadmap 3. Map Customer Journey (Optional) Use: skills/customer journey mapping workshop/SKILL.md (interactive) When to use: If problem spans multiple touchpoints or phases Participants: PM, design, customer success Duration: 90 minutes Output: Journey map with pain points and opportunities Decision Point 2: Is the problem validated? If YES: Proceed to Phase 3 (Solution Exploration) If NO: Run customer discovery interviews: Use: skills/discovery interview prep/SKILL.md (interactive) Validate problem hypothesis with 5 10 customers Iterate problem statement based on findings Time impact: +1 week Phase 3: Solution Exploration (Week 2, Days 1 3) Goal: Generate solution options, prioritize based on feasibility/impact, and select POC. Activities 1. Generate Opportunity Solution Tree Use: skills/opportunity solution tree/SKILL.md (interactive) Participants: PM, design, engineering lead Duration: 90 minutes Output: 3 opportunities, 3 solutions per opportunity, POC recommendation Alternative: Use Lean UX Canvas Use: skills/lean ux canvas/SKILL.md (interactive) When to use: If you prefer hypothesis driven approach over OST Output: Business problem, hypotheses, experiments 2. Define Epic Hypotheses Use: skills/epic hypothesis/SKILL.md (component) Participants: PM Duration: 60 minutes per epic Output: Epic hypothesis statements for top 3 5 initiatives 3. Create User Story Map (Optional) Use: skills/user story mapping workshop/SKILL.md (interactive) When to use: For complex features requiring release planning Participants: PM, design, engineering Duration: 120 minutes Output: Story map with backbone, release slices Decision Point 3: Do we need to test solutions before committing? If YES (high uncertainty): Run experiments: Design POC experiments per skills/opportunity solution tree/SKILL.md output Test with 10 20 customers (prototype, concierge, landing page test) Time impact: +1 2 weeks If NO (low uncertainty): Proceed to Phase 4 (Prioritization) Phase 4: Prioritization & Roadmap Planning (Week 2, Days 4 5) Goal: Prioritize initiatives and sequence into executable roadmap. Activities 1. Choose Prioritization Framework Use: skills/prioritization advisor/SKILL.md (interactive) Participants: PM Duration: 30 minutes Output: Recommended prioritization framework (RICE, ICE, Value/Effort, etc.) 2. Score & Prioritize Epics Use: Prioritization framework from step 1 Participants: PM, engineering lead, product leadership Duration: 90 minutes Output: Ranked backlog of epics 3. Sequence Roadmap by Release Participants: PM, engineering lead Duration: 60 minutes Output: Quarterly or release based roadmap (Q1: Epics A, B; Q2: Epics C, D, E) 4. Map TAM/SAM/SOM (Optional) Use: skills/tam sam som calculator/SKILL.md (interactive) When to use: For exec presentations, fundraising, or market sizing Participants: PM, business ops Duration: 60 minutes Output: Market size projections with citations Phase 5: Stakeholder Alignment & Communication (Week 3) Goal: Present strategy to stakeholders, gather feedback, refine. Activities 1. Create Visionary Press Release (Optional) Use: skills/press release/SKILL.md (component) When to use: For major product launches or exec buy in Participants: PM, marketing Duration: 60 minutes Output: Amazon Working Backwards style press release 2. Present Strategy to Stakeholders Format: 60 min presentation covering: Positioning statement (Phase 1) Problem statement (Phase 2) Solution options & prioritization (Phase 3 4) Roadmap (Phase 4) Participants: Execs, product leadership, key stakeholders Output: Feedback, open questions, approval to proceed 3. Refine Based on Feedback Duration: 1 2 days Output: Updated strategy artifacts Phase 6: Execution Planning (Week 4) Goal: Break epics into user stories, plan first sprint/release. Activities 1. Break Down Top Epic Use: skills/epic breakdown advisor/SKILL.md (interactive with Richard Lawrence's 9 patterns) Participants: PM, design, engineering Duration: 90 minutes Output: User stories split by patterns (workflow, CRUD, business rules, etc.) 2. Write User Stories Use: skills/user story/SKILL.md (component) Participants: PM Duration: 30 minutes per story Output: User stories with acceptance criteria 3. Plan First Sprint/Release Participants: PM, engineering Duration: 60 minutes Output: Sprint backlog or release plan Complete Workflow: End to End Summary Total Time Investment: Minimum: 2 weeks (no discovery/experiments) Typical: 3 weeks (includes 1 round of validation) Maximum: 4 6 weeks (includes discovery interviews + experiments) Examples See examples/sample.md for a full strategy session example. Mini example excerpt: Common Pitfalls Pitfall 1: Skipping Problem Validation Symptom: Jump from positioning to solution exploration without validating problem Consequence: Build solutions to unvalidated problems Fix: Force decision point after Phase 2: "Is problem validated?" If NO, run discovery interviews. Pitfall 2: Solo PM Exercise Symptom: PM runs strategy session alone, presents finished strategy to team Consequence: No buy in, team doesn't understand rationale Fix: Include cross functional participants in workshops (design, eng, sales, CS) Pitfall 3: Strategy Session Without Executive Sponsorship Symptom: Run full strategy session, execs don't show up for Phase 5 alignment Consequence: Strategy doesn't get resourced or prioritized Fix: Secure exec commitment upfront; schedule Phase 5 presentation before starting. Pitfall 4: No Decision Points (Run All Phases Regardless) Symptom: Blindly follow all 6 phases without checking if discovery/experiments are needed Consequence: Waste time on low uncertainty activities Fix: Use decision points after Phase 2 and Phase 3 to adapt workflow. Pitfall 5: Strategy Session Becomes Permanent Process Symptom: Team spends 6 weeks in strategy mode, never executes Consequence: Analysis paralysis, no delivery Fix: Time box strategy session to 2 4 weeks; after Phase 6, move to execution. References Related Skills (Orchestrated b

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