Strategy & Planning Skill
Use this skill when the user is deciding where to go and what bets to make: vision, strategy docs, OKRs, roadmaps, prioritization, and strategic tradeoffs.
When to use this skill
Trigger this skill (usually in product_sense or execution_mode) when the user:
- Says things like:
- “I need to write a strategy doc” - “I’m planning H2 / next year” - “I need to create OKRs / a roadmap” - “I’m not sure which bets to prioritize” - “I’m stuck between these 2–3 big directions”
- Or explicitly mentions:
- Strategy, OKRs, roadmap, north star, prioritization
If their main question is discovery / research, use discovery-research. If it’s mainly about communication and buy-in, use stakeholder-management.
Relevant framework locations
Most strategy frameworks live under:
02-Methods-and-Tools/2.1-Strategy/
- 2.1.1-Strategic-Foundations/ - Strategy foundations, good-strategy/bad-strategy, Playing to Win - 2.1.2-Strategic-Execution/ - 1-OKR/ (OKRs) - 2-Roadmap/ (roadmaps) - 3-North-Star/ (north star metrics) - 4-Prioritization/ (RICE, value/effort, MoSCoW, Kano)
Typical flows
1. “I need a strategy doc”
- In product_sense, clarify:
- What kind of strategy (growth, market entry, pivot, annual plan)? - Who is the audience (execs, peers, team)? - What decisions should this doc help them make?
- Use:
- 2.1-Strategy/2.1.1-Strategic-Foundations/README.md - And, if helpful, a specific framework like: - 2.1.1-Strategic-Foundations/2-Good-Strategy-Bad-Strategy/1-good-strategy-bad-strategy-framework.md - 2.1.1-Strategic-Foundations/3-Playing-To-Win/1-playing-to-win-framework.md
- Transition to execution_mode:
- Propose a structure that fits the context (e.g., context → choices → actions). - Pull from the user’s braindump to outline the sections.
2. “Help me set OKRs”
- Clarify:
- Timeframe and scope (team vs organization, quarter vs half). - How OKRs will be used (alignment vs strict commitment). - Org reality check: Ask whether OKRs are genuinely outcome-driven in this org or function more as a coordination/capacity label. If the latter, acknowledge it — help the user run their own outcome tracking privately and use OKR language externally where it lands, without pretending the org process is something it isn't.2. Point to: - 2.1-Strategy/2.1.2-Strategic-Execution/1-OKR/1-okr-framework.md
- Then:
- In execution_mode, use 2-okr-template.md to structure objectives and key results. - Use 3-okr-evaluation.md for a quick quality check before sharing.
3. “I need a roadmap”
- Clarify:
- Purpose (alignment vs commitment vs exploration). - Audience (execs, team, cross-functional partners).
- Point to:
- 2.1-Strategy/2.1.2-Strategic-Execution/2-Roadmap/1-roadmap-framework.md
- Help choose:
- A simple starting format (now/next/later, or quarters with themes). - Then use 2-roadmap-template.md and 3-roadmap-evaluation.md as needed.
4. “I need to prioritize features / bets”
- Explore:
- What constraints matter most (capacity, risk, revenue, learning)? - Whether they need a lightweight or more rigorous approach.
- Use:
- 2.1-Strategy/2.1.2-Strategic-Execution/4-Prioritization/decision-tree.md to pick an approach. - RICE, value/effort, MoSCoW, or Kano from that folder as appropriate.
Response guidelines
- Stay in product_sense until the problem is clear
- Ask about goals, audience, decisions, and constraints before suggesting frameworks.
- Match framework to situation
- Use when-to-use-which.md in Strategic Foundations where helpful.
- Anchor to company context
- When relevant, wake: - 01-Company-Context/2-company-strategy.md - 01-Company-Context/5-company-roadmap.md - So strategy artifacts align with existing direction.
- Be explicit about tradeoffs
- When comparing options, help them define decision criteria, not just pick a framework.
Relation to other skills
pm-brain-workflowdecides where in the Foundations → Strategy → Discovery → Execution → Communication flow you are.strategy-planningdeepens the Strategy slice: strategy docs, OKRs, roadmaps, prioritization.- Use
discovery-researchwhen the main need is learning and evidence. - Use
stakeholder-managementwhen the main need is alignment and communication.