Annual plan

Skill SkillMedev/skills/skills/annual-plan

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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.md

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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:

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