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.
1---2name: annual-planning3description: 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.4---56# Annual Planning78Annual planning fails when it becomes a budget exercise disconnected from9strategy, or a wish-list with no prioritization. Done well, it produces a small10set of priorities the whole company can rally behind. This skill structures the11cycle end to end.1213## Start With Strategy, Not the Calendar1415Before any goals, answer the strategic questions:1617- Where are we now, honestly? (Reflect on last year: what worked, what did not,18 what surprised us.)19- What is the single most important thing we must achieve this year to win?20- What are we explicitly NOT doing? A plan with no "no" is not a plan.2122The output of this stage is a point of view, not a spreadsheet.2324## The Planning Cadence2526A typical 6-8 week cycle:27281. **Leadership offsite**: agree the strategic context and the 3-5 company29 priorities for the year.302. **Top-down framing**: leadership publishes the priorities and rough resource31 envelope.323. **Bottom-up planning**: teams propose how they will contribute, with OKRs33 and resource needs.344. **Reconciliation**: align top-down ambition with bottom-up capacity; cut35 until it is realistic.365. **Finalize and communicate**: lock OKRs, budget, and the CEO memo.3738The bottom-up step matters - plans imposed top-down get compliance, not39commitment.4041## Setting OKRs4243- **Objectives**: qualitative, ambitious, memorable - what we want to achieve.44- **Key Results**: measurable outcomes that prove the objective, not a task45 list. "Ship feature X" is a task; "Increase activation to 40%" is a KR.46- Limit to 3-5 objectives at the company level; more means no focus.47- Cascade so every team's OKRs ladder up to a company priority. If a team's48 work maps to none, question whether it should be funded.4950## Resource Allocation5152- Allocate people and budget to the priorities deliberately; if everything is53 funded, nothing is prioritized.54- Run the trade-offs explicitly: to fund priority A, what gets cut or delayed?55- Leave slack - a fully-committed plan has no room for the year's surprises.5657## The CEO Memo5859Cap the cycle with a written narrative memo (not just slides):6061- The strategic context and why these priorities.62- The 3-5 priorities and what success looks like.63- What we are deliberately not doing and why.64- How resources are allocated to match.6566A written memo forces clarity that bullet points let you dodge, and it becomes67the reference all year.6869## Keeping It Alive7071- Review OKRs quarterly; grade them honestly and re-plan as reality shifts.72- Make priorities visible - the plan should be referenced in everyday73 decisions, not filed away.7475## Anti-Patterns7677- Too many priorities (focus dies).78- KRs that are tasks, not outcomes.79- A plan that is never revisited until next year's cycle.80- Budget-led planning with strategy bolted on afterward.8182## Deliverable8384Produce an annual plan package: the strategic reflection, 3-5 company85priorities with cascaded OKRs, a resource-allocation view with explicit86trade-offs, a quarterly review cadence, and the CEO narrative memo.
SkillMedev