Individual skill

annual-plan

Runs an annual planning cycle end to end - strategic reflection, 3-5 company priorities with explicit not-doing decisions, cascaded OKRs reconciled between top-down framing and bottom-up team plans, resource allocation with named trade-offs, a quarterly review cadence, and the CEO narrative memo. Use when a leader asks "run our annual planning", "set next year's company priorities", "our planning is just a budget exercise", or needs to turn a leadership offsite into a committed plan. Do NOT use for writing a single team's quarterly OKRs - use okr-builder instead; for a product-specific roadmap, use product-roadmap.

skills/annual-plan/SKILL.md

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Repository last updated: Oct 13, 2026
License: MIT

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# Annual Planning

Annual planning fails when it becomes a budget exercise disconnected from
strategy, or a wish-list with no prioritization. Done well, it produces a small
set of priorities the whole company can rally behind. This skill structures the
cycle end to end.

## Start With Strategy, Not the Calendar

Before any goals, answer the strategic questions:

- Where are we now, honestly? (Reflect on last year: what worked, what did not,
  what surprised us.)
- What is the single most important thing we must achieve this year to win?