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”

1. 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?
2. 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
3. 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”

1. 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
2. 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”

1. Clarify:
   • Purpose (alignment vs commitment vs exploration).
   • Audience (execs, team, cross-functional partners).
2. Point to:
   • 2.1-Strategy/2.1.2-Strategic-Execution/2-Roadmap/1-roadmap-framework.md
3. 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”

1. Explore:
   • What constraints matter most (capacity, risk, revenue, learning)?
   • Whether they need a lightweight or more rigorous approach.
2. 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

1. Stay in product_sense until the problem is clear
   • Ask about goals, audience, decisions, and constraints before suggesting frameworks.
2. Match framework to situation
   • Use when-to-use-which.md in Strategic Foundations where helpful.
3. 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.
4. Be explicit about tradeoffs
   • When comparing options, help them define decision criteria, not just pick a framework.

Relation to other skills

• pm-brain-workflow decides where in the Foundations → Strategy → Discovery → Execution → Communication flow you are.
• strategy-planning deepens the Strategy slice: strategy docs, OKRs, roadmaps, prioritization.
• Use discovery-research when the main need is learning and evidence.
• Use stakeholder-management when the main need is alignment and communication.