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).

• 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-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.