product-strategy-session skill

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 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