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.
Install
The skill file stays in the publisher's repository.
Paste the copied command in a terminal. It installs this SKILL.md into that agent.
npx skills add deanpeters/Product-Manager-Skills --skill product-strategy-session -a cursor -y
Download skills/product-strategy-session/SKILL.md from the publisher, or copy the path and open the repository. PlugMCP lists the skill and does not host the file.
Where does product-strategy-session live?
The publisher keeps it at https://github.com/deanpeters/Product-Manager-Skills.
Which agents can use product-strategy-session?
Claude, Cursor, and Codex can read a SKILL.md you add from the publisher's repository.
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.
name: product-strategy-session
argument-hint: "[product or strategic question]"
description: 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.
intent: >-
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.
type: workflow
theme: strategy-positioning
best_for:
"Running a full strategy arc from positioning through roadmap"
"Giving a team validated direction instead of a feature list"
"Aligning leadership on where the product is going and why"
scenarios:
"Our team has a backlog but no direction and leadership wants a strategy"
"We need to go from positioning through discovery to a roadmap people believe"
estimated_time: "2-4 weeks"
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:
Positioning & Market Context — Define who you serve, what problem you solve, and how you're differentiated
Problem Discovery & Validation — Frame and validate customer problems through research
Solution Exploration — Generate opportunity solutions and prioritize based on impact
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.
[If Dean has strategy session resources, link here]
Skill type: Workflow
Suggested filename:product-strategy-session.mdSuggested placement:/skills/workflows/Dependencies: Orchestrates 15+ component and interactive skills across 6 phases
How do I install product-strategy-session?
Download skills/product-strategy-session/SKILL.md from the publisher, or copy the path and open the repository. PlugMCP lists the skill and does not host the file.
Where does product-strategy-session live?
The publisher keeps it at https://github.com/deanpeters/Product-Manager-Skills.
Which agents can use product-strategy-session?
Claude, Cursor, and Codex can read a SKILL.md you add from the publisher's repository.