Updated October 2026
‘Tis the season for cozy sweaters, holiday cheer… and annual planning!
Annual planning is a dedicated session where your leadership team steps back, revisits where you’re headed, and commits to the handful of priorities that matter most for the year ahead. Done well, it turns a big vision into a focused plan your whole team can execute on from week one.
Haven’t scheduled yours yet? Don’t worry, it’s not too late. Late fall is ideal and January works great too. Honestly, the best time to plan is whenever you start. Don’t wait for the perfect moment. Pick a date and move forward.
Here are four essentials to make your session both effective and inspiring:
1. Revisit Your Vision
Start with the big picture: your Core Values, Purpose, Brand Promises, and your Big, Hairy, Audacious Goal (BHAG). Then revisit your 3–5 year goals. Your annual plan should be a clear stepping stone toward them.
This is where Future-Back thinking shines. Instead of asking “what can we get done next year?”, picture where you want to be in 3–5 years and work backward. Your vision doesn’t need to be an exact destination. It needs to be directional, clear enough that everyone is rowing the same way.
Key Questions:
Fast-forward to the end of next year. What big wins are we celebrating?
How do those wins move us toward our 3–5 year goals and our BHAG?
2. Reflect & Celebrate
Before you look ahead, take a moment to look back. Reflection isn’t about dwelling on what went wrong. It’s about learning, celebrating, and carrying the right lessons forward. Gather perspectives from across the team, not just the top.
Key Questions:
What were our biggest wins this past year?
Where did the team really excel?
What got in our way, and what will we do differently next year?
3. Protect the Time
Great planning takes focus. Block the calendars, move the meetings, and show your team this matters. The more distraction-free the session, the better the plan, and the easier every quarterly session after it becomes.
Plan for two full days to leave room for both strategic thinking and execution planning. Your annual session can double as Q1 planning, so you hit the ground running in January. To really level up, take it offsite. A change of scenery sparks creativity, cuts interruptions, and makes deep thinking easier. Plus, it’s fun!
Key Questions:
What environment will help our team focus and think big?
How much uninterrupted time do we need to plan the year well?
4. Bring in a Coach
It’s really hard to be both a participant and the facilitator. Your CEO or founder belongs in the conversation, not running it. A coach keeps the session moving, asks the tough questions, and makes sure every voice is heard.
A great coach also brings proven tools. In Verne Harnish’s Scaling Up methodology, that means frameworks like the One-Page Strategic Plan, which captures your vision, annual priorities, and quarterly Rocks on a single page your team will actually use.
The best part? A coach guides you through the first three essentials, so your vision, reflection, and focus all come together in one plan.
Key Questions:
Who is facilitating our planning session?
How can a coach help us build a plan that’s ambitious and achievable?
What a Two-Day Session Can Look Like
Day 1: Look back, look ahead
Celebrate wins and lessons from the past year
Revisit your Core Values, Purpose, and BHAG
Work Future-Back from your 3–5 year goals
Review market trends and your SWOT
You walk away with: a shared picture of where you’re headed and what’s changed.
Day 2: Commit
Set 3–5 annual priorities and your Critical Number
Set Q1 Rocks with clear owners
Pick a Q1 theme
Confirm your meeting rhythm
You walk away with: a One-Page Strategic Plan and a Q1 plan, ready to execute.
Frequently Asked Questions
When should we do annual planning?
Most teams plan in November or December so they’re ready to execute on day one of the new year. January works well too. If you’re reading this mid-year, don’t wait. Start now and plan the next four quarters.
How long should an annual planning session take?
Two full days is ideal. That gives you time for big-picture strategy on Day 1 and concrete priorities and Q1 Rocks on Day 2.
Who should attend?
Your leadership team, the people accountable for executing the plan. Keep the group small enough for real conversation, usually 5–10 people.
What should we walk away with?
An updated One-Page Strategic Plan: your vision, 3–5 annual priorities, a Critical Number for the year, and Q1 Rocks with clear owners.
Do we really need an outside facilitator?
It helps a lot. When the CEO facilitates, they can’t fully participate, and the team tends to defer to them. A Scaling Up coach keeps the session focused and brings proven tools to the table.
A Final Thought
Annual planning isn’t about building a to-do list. It’s about crafting a strategic roadmap that moves you closer to your vision. Reflect on where you’ve been, align on where you’re going, and give the plan the time it deserves. You’ll set your team up for an amazing year.
Ready to plan your best year yet? Let’s get your annual planning session on the calendar.
