# Annual Planning

> 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.

- Skill: `skillmedev/annual-planning` (Agent Skill)
- Install (CLI): `npx skillmds@latest add skillmedev/annual-planning`
- Raw SKILL.md: https://api.skillmd.com/api/skills/skillmedev/annual-planning/raw
- Safety review: pending
- Works with: Claude Code, Claude.ai, OpenAI Codex
- Category: Product & Planning
- Author: SkillMedev (https://skillmd.com/u/skillmedev)
- Updated: 2026-09-22
- Page: https://skillmd.com/skills/skillmedev/annual-planning

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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?
- What are we explicitly NOT doing? A plan with no "no" is not a plan.

The output of this stage is a point of view, not a spreadsheet.

## The Planning Cadence

A typical 6-8 week cycle:

1. **Leadership offsite**: agree the strategic context and the 3-5 company
   priorities for the year.
2. **Top-down framing**: leadership publishes the priorities and rough resource
   envelope.
3. **Bottom-up planning**: teams propose how they will contribute, with OKRs
   and resource needs.
4. **Reconciliation**: align top-down ambition with bottom-up capacity; cut
   until it is realistic.
5. **Finalize and communicate**: lock OKRs, budget, and the CEO memo.

The bottom-up step matters - plans imposed top-down get compliance, not
commitment.

## Setting OKRs

- **Objectives**: qualitative, ambitious, memorable - what we want to achieve.
- **Key Results**: measurable outcomes that prove the objective, not a task
  list. "Ship feature X" is a task; "Increase activation to 40%" is a KR.
- Limit to 3-5 objectives at the company level; more means no focus.
- Cascade so every team's OKRs ladder up to a company priority. If a team's
  work maps to none, question whether it should be funded.

## Resource Allocation

- Allocate people and budget to the priorities deliberately; if everything is
  funded, nothing is prioritized.
- Run the trade-offs explicitly: to fund priority A, what gets cut or delayed?
- Leave slack - a fully-committed plan has no room for the year's surprises.

## The CEO Memo

Cap the cycle with a written narrative memo (not just slides):

- The strategic context and why these priorities.
- The 3-5 priorities and what success looks like.
- What we are deliberately not doing and why.
- How resources are allocated to match.

A written memo forces clarity that bullet points let you dodge, and it becomes
the reference all year.

## Keeping It Alive

- Review OKRs quarterly; grade them honestly and re-plan as reality shifts.
- Make priorities visible - the plan should be referenced in everyday
  decisions, not filed away.

## Anti-Patterns

- Too many priorities (focus dies).
- KRs that are tasks, not outcomes.
- A plan that is never revisited until next year's cycle.
- Budget-led planning with strategy bolted on afterward.

## Deliverable

Produce an annual plan package: the strategic reflection, 3-5 company
priorities with cascaded OKRs, a resource-allocation view with explicit
trade-offs, a quarterly review cadence, and the CEO narrative memo.