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Annual Planning Calendar

A template for the annual planning calendar.

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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

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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.