| name | annual-planning |
| description | Facilitates annual business planning with vision setting, goal cascading, quarterly milestones, and resource allocation for focused execution. |
| allowed-tools | Read Write Glob |
| metadata | {"author":"matthewhitcham","version":"1.0"} |
Annual Planning
When to Use This Skill
Use this skill when you need to:
- Create a comprehensive annual business plan with goals and milestones
- Break yearly objectives into quarterly and monthly targets
- Allocate resources (time, money, energy) across priorities
- Set a strategic direction for the coming year with measurable outcomes
DO NOT use this skill for weekly planning, project planning, or financial forecasting. This is for high-level annual strategic planning.
Core Principle
AN ANNUAL PLAN IS NOT A WISH LIST — IT IS A RESOURCE ALLOCATION DOCUMENT THAT FORCES YOU TO SAY NO TO GOOD IDEAS SO YOU CAN SAY YES TO THE BEST ONES.
Phase 1: Reflect
Review the past year before planning the next one.
Required Inputs
| Input | What to Ask | Default |
|---|
| Last year's revenue | "What was your revenue last year?" | No default |
| Last year's wins | "What were your top 3 accomplishments?" | No default |
| Last year's misses | "What did you plan to do but didn't?" | No default |
| Biggest lesson | "What is the one thing you learned about your business this year?" | No default |
| Current team | "Who is on your team and what do they handle?" | Solopreneur |
| Available budget | "What is your approximate budget for growth initiatives?" | Limited |
Year in Review Template
## [Previous Year] in Review
**Revenue:** $[X] ([+/-X%] vs. prior year)
**Top 3 Wins:**
1. [Win + impact]
2. [Win + impact]
3. [Win + impact]
**Top 3 Misses:**
1. [What was planned + why it didn't happen]
2. [What was planned + why it didn't happen]
3. [What was planned + why it didn't happen]
**Key Lesson:** [One sentence]
**What to keep doing:** [Activities that drove results]
**What to stop doing:** [Activities that wasted time]
**What to start doing:** [New activities for next year]
GATE: Complete the review before setting new goals.
Phase 2: Set Goals
Define the annual vision and break it into goals.
Annual Theme
Every year gets a single theme — one word or phrase that guides every decision:
**[Year] Theme:** [e.g., "Scale," "Profit First," "Foundation Building," "Diversify"]
Goal Framework
Set 3-5 annual goals using this structure:
## [Year] Goals
### Goal 1: [Specific, Measurable Outcome]
**Metric:** [How you measure success]
**Target:** [Number or milestone]
**Why it matters:** [Connection to business vision]
**Resources needed:** [Time, money, people]
### Goal 2: [Specific, Measurable Outcome]
...
Goal Quality Check
Every goal must pass these tests:
- Specific: Can you explain it in one sentence?
- Measurable: Is there a number or clear milestone?
- Achievable: Do you have the resources to pursue it?
- Relevant: Does it connect to the annual theme?
- Time-bound: Does it have a deadline within the year?
GATE: Confirm annual goals before cascading into quarters.
Phase 3: Quarterly Cascade
Break annual goals into quarterly milestones and monthly actions.
Quarterly Milestone Map
## Quarterly Milestones
### Q1: [Theme — e.g., "Build Foundation"]
| Goal | Q1 Milestone | Key Actions | Success Metric |
|------|-------------|-------------|---------------|
| Goal 1 | [Milestone] | [2-3 actions] | [Metric] |
| Goal 2 | [Milestone] | [2-3 actions] | [Metric] |
### Q2: [Theme — e.g., "Launch and Test"]
| Goal | Q2 Milestone | Key Actions | Success Metric |
|------|-------------|-------------|---------------|
| Goal 1 | [Milestone] | [2-3 actions] | [Metric] |
### Q3: [Theme — e.g., "Optimize"]
...
### Q4: [Theme — e.g., "Scale and Prepare"]
...
Resource Allocation
## Resource Allocation
| Resource | Total Available | Goal 1 | Goal 2 | Goal 3 | Buffer |
|----------|---------------|--------|--------|--------|--------|
| Time (hrs/week) | [X] | [X] | [X] | [X] | [X] |
| Budget | $[X] | $[X] | $[X] | $[X] | $[X] |
| Team capacity | [X people] | [X] | [X] | [X] | — |
Rule: Always allocate a 10-20% buffer for unexpected opportunities or emergencies.
Phase 4: Execution System
Set up the rhythm that keeps the plan alive throughout the year.
Review Cadence
## Planning Review Rhythm
**Weekly (15 min):** Review this week's actions against monthly targets
**Monthly (30 min):** Review monthly progress against quarterly milestones
**Quarterly (2 hours):** Full quarterly review — adjust goals, reallocate resources
**Annually (half day):** Full annual review and next year planning
Quarterly Review Template
## Q[X] Review
**Goal progress:**
| Goal | Target | Actual | Status | Adjustment |
|------|--------|--------|--------|-----------|
| [Goal] | [Target] | [Actual] | On track / Behind / Ahead | [Change if needed] |
**What worked this quarter:**
**What didn't work:**
**Adjustments for next quarter:**
Annual Plan One-Pager
Distill the entire plan into a single page that can be posted visibly:
## [Year] Annual Plan — One Page
**Theme:** [Word/Phrase]
**Revenue target:** $[X]
**Top 3 Goals:**
1. [Goal + target metric]
2. [Goal + target metric]
3. [Goal + target metric]
**Q1 Focus:** [One sentence]
**Q2 Focus:** [One sentence]
**Q3 Focus:** [One sentence]
**Q4 Focus:** [One sentence]
Anti-Patterns
- Too many goals — more than 5 annual goals means nothing gets the focus it needs. Ruthlessly prioritize.
- No quarterly milestones — annual goals without quarterly checkpoints drift until December panic.
- Planning without reviewing — skipping the year-in-review means repeating last year's mistakes.
- No resource allocation — goals without time and budget attached are fantasies, not plans.
- Set it and forget it — the plan is a living document. Quarterly reviews keep it relevant.
Recovery
- User has never done annual planning: Start with just 2 goals and quarterly milestones. Add complexity in future years.
- Last year had no clear goals: Use revenue, customers, and personal satisfaction as proxy metrics for the review.
- User sets goals too aggressively: Apply the "50% rule" — if you achieve 50% of an aggressive plan, is that still a great year? If yes, keep it. If not, scale back.
- Mid-year and no plan exists: Do a mid-year plan. Same process, 6-month horizon. Better late than never.
- User is overwhelmed by the process: Complete it in two sessions — Session 1 for review and goals, Session 2 for quarterly cascade and execution system.
