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Annual Planning Calendar
A template for the annual planning calendar.
What's included
- Key planning milestones
- Stakeholder involvement
- Document deadlines
- Review meetings
- Communication timeline
Best used when
- Setting planning rhythms
- Coordinating stakeholders
- Managing planning process
- Ensuring planning completion
The template
The Template
PLANNING OVERVIEW
Planning Philosophy
ANNUAL PLANNING PRINCIPLES
PLANNING PHILOSOPHY:
☐ Strategy is ongoing, not annual
☐ Planning enables, doesn't constrain
☐ Involve the right people early
☐ Balance rigor with speed
☐ Plans change; planning matters
PLANNING OUTPUTS:
1. 3-Year Strategic Direction (updated)
2. Annual Company Priorities (3-5)
3. Department Goals (aligned)
4. Budget and Headcount Plan
5. OKRs for Q1
PLANNING RHYTHMS:
Annual: Full strategy refresh
Quarterly: QBR and goal setting
Monthly: Progress review
Weekly: Execution focus
CALENDAR TEMPLATE
Annual Planning Calendar
ANNUAL PLANNING CALENDAR
Q1 - EXECUTION + KICKOFF
JANUARY:
Week 1: Company kickoff meeting
Week 2: Q1 sprint starts
Week 3: Department goals finalized
Week 4: Board meeting (Q4 results)
FEBRUARY:
Week 1-4: Q1 execution
Mid-month: Pulse check
MARCH:
Week 1-2: Q1 execution
Week 3: Q1 close preparation
Week 4: Q1 review, Q2 OKR setting
---
Q2 - EXECUTION + MID-YEAR
APRIL:
Week 1: Q2 start
Week 2-4: Q2 execution
Month-end: Board meeting (Q1 results)
MAY:
Week 1-4: Q2 execution
Begin mid-year planning prep
JUNE:
Week 1-2: Q2 execution
Week 3: Mid-year review
Week 4: Q2 close, Q3 planning
---
Q3 - EXECUTION + PLANNING PREP
JULY:
Week 1: Q3 start
Week 2-4: Q3 execution
Month-end: Board meeting (Q2 results)
AUGUST:
Week 1-2: Q3 execution
Week 3: Planning kickoff (market analysis)
Week 4: Collect department inputs
SEPTEMBER:
Week 1: Strategic retreat prep
Week 2: STRATEGIC RETREAT
Week 3: Q3 close, draft strategy
Week 4: Q4 OKR setting
---
Q4 - PLANNING + WRAP-UP
OCTOBER:
Week 1: Q4 start
Week 2: Strategy refinement
Week 3: Department planning begins
Week 4: Draft budget, Board meeting (Q3 results)
NOVEMBER:
Week 1: Budget reviews
Week 2: Finalize headcount
Week 3: OKR drafting for next year
Week 4: Board budget review
DECEMBER:
Week 1: Final budget/plan adjustments
Week 2: Board approval
Week 3: Communication prep
Week 4: Q4 close, year-end
Monthly Planning Checklist
| Month | Key Activity | Deadline | Owner |
|---|---|---|---|
| Jan | Company kickoff | Week 1 | CEO |
| Feb | Q1 execution | Ongoing | All |
| Mar | Q1 review | Week 4 | CEO |
| Apr | Q2 start | Week 1 | All |
| May | Mid-year prep | Week 3 | CoS |
| Jun | Mid-year review | Week 3 | CEO |
| Jul | Q3 start | Week 1 | All |
| Aug | Planning kickoff | Week 3 | CEO |
| Sep | Strategic retreat | Week 2 | CEO |
| Oct | Dept planning | Ongoing | VPs |
| Nov | Budget finalize | Week 3 | CFO |
| Dec | Board approval | Week 2 | CEO |
STAKEHOLDER INVOLVEMENT
RACI Matrix
PLANNING RACI MATRIX
R = Responsible (does the work)
A = Accountable (decision maker)
C = Consulted (provides input)
I = Informed (kept in loop)
| Activity | CEO | CFO | CRO | CPO | Board |
|----------|-----|-----|-----|-----|-------|
| Market analysis | A | C | R | C | I |
| Strategy retreat | A | R | R | R | I |
| Company priorities | A | C | C | C | A |
| Dept goals | A | R | R | R | I |
| Budget | A | R | C | C | A |
| Headcount | A | R | C | C | A |
| OKRs | A | C | R | R | I |
| Communication | A | I | R | R | I |
Stakeholder Engagement Timeline
STAKEHOLDER ENGAGEMENT
BOARD:
☐ Sep: Heads up on planning timeline
☐ Oct: Q3 results + planning preview
☐ Nov: Draft strategy review
☐ Dec: Budget and plan approval
☐ Jan: Q4 results + approved plan
EXECUTIVES:
☐ Aug: Planning kickoff
☐ Sep: Strategic retreat
☐ Oct: Department planning
☐ Nov: Budget reviews
☐ Dec: Final alignment
DEPARTMENT HEADS:
☐ Sep: Planning inputs due
☐ Oct: Draft department plans
☐ Nov: Budget finalization
☐ Dec: OKR finalization
ALL EMPLOYEES:
☐ Dec: High-level preview
☐ Jan: Company kickoff
☐ Jan: Team-level goals shared
Frequently asked questions
What is the Annual Planning Calendar?
A template for the annual planning calendar.
Who is the Annual Planning Calendar for?
It is built for CEOs and their teams working on Strategic Planning. The AI coach adapts it to your company, stage, and goals.
How long does the Annual Planning Calendar take to use?
It saves roughly 20+ hours versus building from scratch. Our AI coach can tailor the template to your situation in minutes, then hand you a step-by-step plan.
Is the Annual Planning Calendar free?
Yes. You can read the full template and start getting coached through it for free. Sign in to save your tailored version and track your next steps.
How does the AI coach help with the Annual Planning Calendar?
The coach teaches you the framework, asks a few questions about your business, tailors the template to you, and gives you measurable next steps to execute.