A four-part annual planning process that actually sticks

Executive overview

Most annual planning fails because founders spend 90% of their time on tactics and skip the thinking. This process inverts that: 50% of the time is pure thinking, with goal-setting and execution planning treated as downstream outputs.

The result is a plan you'll still care about in February.

The core insight: clarity on where you are and where you're going makes the path obvious — but most people skip straight to the path.

What annual planning is not

• Setting a big revenue goal, then breaking it into quarterly/monthly/daily tasks
• Spending most of your time building elaborate tracking systems
• This approach produces plans that get scrapped within two months
• The failure mode: you plan things you don't actually care about

Part 1: Thinking (50% of total time)

Spend a full day — sometimes two — on thinking before any planning begins.

Vision and mission review

• Revisit your company vision and mission as the opening move
• Check that it still resonates and feels compelling
• Purpose: get your head oriented beyond the one-year horizon before zooming in

Point A: where you are now

• Identify what hurts — a reliable signal of systemic problems worth fixing
• If gut instinct is unclear, use a SWOT analysis or audit where time, energy, and money are going
• Review financial data, time-tracking data, and your ideas list
• Rewatch or re-read quarterly reviews to capture how you felt each quarter

Point Z: where you want to end up

• Ask: what competency do I want to have by year-end that I don't have now?
• Competency captures people, skills, processes, and experience — more useful than a revenue figure
• Make it vivid: be able to see and feel the destination, not just describe it

The scale check (three questions)

• Big: does this have disproportionate return? What makes the six-year plan a six-month plan?
• Proud (the grandma check): are you so proud of it you'd send a photo to your grandma even if she wouldn't understand?
• Inspiring: would you lose track of time working toward it day to day?
• If any check fails, go back and revisit Point A or Point Z

Part 2: Goal setting (roughly two hours)

Goals anchor vision to reality. Two categories only.

Big numbers (in priority order)

1. Savings — maintain three to six months of operating expenses in reserve
2. Expenses — the only number you fully control; decide what you want to spend
3. Profit — decide how much to retain vs. withdraw, and why
4. Revenue — reverse-engineered from the above, not the starting point

Role metrics

• Break big numbers into leading indicators for each person on the team
• Large numbers feel out of reach; smaller goalposts drive consistent action
• Example: if 1% of page visitors convert, work backward from revenue to required traffic

Part 3: Communication (a few hours)

Ideas sharpen through debate. Share before finalising.

• Record a video or write up Point A → Point Z and send to leadership, a mastermind, or a trusted advisor
• Ask them to poke holes, disagree, and find what's confusing
• Run a quarterly planning day with your leadership team (or your future self) to refine the journey
• CEO's job: define A and Z. The team bridges the gap.
• After refining, sell the vision — get stakeholders genuinely excited about it
• If it's hard to sell, that's a signal to go refine the vision further

Part 4: Planning (half to one full day, ~30% of time)

Only now do you plan. Two categories.

Existing commitments

• Company promises: offers, waitlists, guarantees already made
• Repeatable wins: seasonal campaigns, team retreats, routines worth keeping
• Life promises: personal vacations and time off — block these before filling in projects

New projects (growth projects)

• Define the what: the functional area or initiative, not a full project plan
• Estimate rough scale: is this three days or three months?
• Assign the who:
  • Coordinator — drives the project, herds the cats
  • Contributors — doing the work
  • Consultants — sounding board only, not hands-on
• Determine order, not dates — which projects must come before others?

Keeping the plan alive

• Revisit the plan every quarter with the leadership team
• Half-day check: does this still make sense? Refine if needed
• Expect 80–90% accuracy by year-end; projects running long is the most common disruption
• The annual plan is a compass, not a contract