product-strategy-session

$2a

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 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

Week 1:

├─ Day 1-2: Positioning & Market Context

│  ├─ skills/positioning-workshop/SKILL.md (90 min)

│  ├─ skills/proto-persona/SKILL.md (60 min)

│  └─ skills/jobs-to-be-done/SKILL.md (60 min)

│

├─ Day 3-5: Problem Framing & Validation

│  ├─ skills/problem-framing-canvas/SKILL.md (120 min)

│  ├─ skills/problem-statement/SKILL.md (30 min)

│  └─ [Optional] skills/customer-journey-mapping-workshop/SKILL.md (90 min)

│

└─ Decision: Validate problem? (if NO, +1 week discovery)

Week 2:

├─ Day 1-3: Solution Exploration

│  ├─ skills/opportunity-solution-tree/SKILL.md (90 min)

│  ├─ skills/epic-hypothesis/SKILL.md (60 min per epic)

│  └─ [Optional] skills/user-story-mapping-workshop/SKILL.md (120 min)

│

├─ Decision: Test solutions? (if YES, +1-2 weeks experiments)

│

└─ Day 4-5: Prioritization & Roadmap

   ├─ skills/prioritization-advisor/SKILL.md (30 min)

   ├─ Score & prioritize epics (90 min)

   ├─ Sequence roadmap (60 min)

   └─ [Optional] skills/tam-sam-som-calculator/SKILL.md (60 min)

Week 3:

└─ Stakeholder Alignment

   ├─ [Optional] skills/press-release/SKILL.md (60 min)

   ├─ Present strategy (60 min)

   └─ Refine based on feedback (1-2 days)

Week 4:

└─ Execution Planning

   ├─ skills/epic-breakdown-advisor/SKILL.md (90 min)

   ├─ skills/user-story/SKILL.md (30 min per story)

   └─ Plan first sprint (60 min)

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:

**Target:** Non-technical SMB owners

**Problem:** Onboarding drop-off due to jargon

**Priority:** Guided onboarding (RICE)

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 by This Workflow)

Phase 1:

• skills/positioning-workshop/SKILL.md (interactive)

• skills/proto-persona/SKILL.md (component)

• skills/jobs-to-be-done/SKILL.md (component)

Phase 2:

• skills/problem-framing-canvas/SKILL.md (interactive)

• skills/problem-statement/SKILL.md (component)

• skills/customer-journey-mapping-workshop/SKILL.md (interactive, optional)

• skills/discovery-interview-prep/SKILL.md (interactive, if validation needed)

Phase 3:

• skills/opportunity-solution-tree/SKILL.md (interactive)

• skills/lean-ux-canvas/SKILL.md (interactive, alternative)

• skills/epic-hypothesis/SKILL.md (component)

• skills/user-story-mapping-workshop/SKILL.md (interactive, optional)

Phase 4:

• skills/prioritization-advisor/SKILL.md (interactive)

• skills/tam-sam-som-calculator/SKILL.md (interactive, optional)

Phase 5:

• skills/press-release/SKILL.md (component, optional)

Phase 6:

• skills/epic-breakdown-advisor/SKILL.md (interactive)

• skills/user-story/SKILL.md (component)

External Frameworks

• Teresa Torres, Continuous Discovery Habits (2021) — Opportunity solution tree framework

• Jeff Gothelf, Lean UX (2016) — Hypothesis-driven product development

• Marty Cagan, Inspired (2017) — Product discovery process

Dean's Work

• Productside Blueprint — Strategic product discovery

• [If Dean has strategy session resources, link here]

Skill type: Workflow

Suggested filename: product-strategy-session.md

Suggested placement: /skills/workflows/

Dependencies: Orchestrates 15+ component and interactive skills across 6 phases