Annual Planning: How to Run Your 2027 Planning Offsite (+ Template)

Annual planning is where a leadership team decides what the company will focus on next year, what it will stop doing, and who owns each goal. Many teams do it in a string of meetings squeezed between other work. The best plans usually come out of a focused one- or two-day offsite.

An annual planning offsite is a type of strategic planning retreat focused on the year ahead. This guide covers the pre-work, the agenda and the follow-up, with a template you can copy.

Key Takeaways

• Annual planning sets next year's priorities, goals, owners and budget, and it works best as a focused offsite away from day-to-day work.
• Most of the work happens before the offsite: a review of this year's results, leader interviews and draft priorities.
• Limit the plan to three to five company priorities, each with an owner and a measurable goal.
• A two-day agenda gives time to review, debate, decide and commit without rushing.
• Share a one-page plan within a week, then review progress every quarter.

What is annual planning?

Annual planning is the process of setting a company's priorities, goals and resources for the coming year. It usually produces:

• Three to five company priorities for the year.
• Measurable goals for each priority, often as OKRs or KPIs.
• Owners for every priority and goal.
• A budget and headcount plan that matches the priorities.
• A review rhythm, usually quarterly, to track progress and adjust.

It's narrower than multi-year strategic planning. The strategy sets the direction for three to five years; annual planning decides what the company does about it next year.

When to hold your annual planning offsite

Most companies plan the following year in October or November. That leaves time to finalize budgets before January and share the plan at the company kickoff. If your fiscal year doesn't follow the calendar, plan about two to three months before it starts.

Avoid quarter-end weeks, when sales and finance leaders are focused on closing the year, and major holidays such as Rosh Hashanah and Yom Kippur in early October 2027.

Before the offsite: the pre-work

The quality of the plan depends on the pre-work. Three to four weeks before the offsite:

1. Review this year. Collect results against each goal, what worked and what didn't.
2. Interview each leader. Ask what the company should start, stop and continue, and what worries them about next year.
3. Gather inputs: financial forecasts, customer data, market changes and team capacity.
4. Draft the options. Turn the inputs into a short list of possible priorities to debate, not a finished plan.
5. Send a pre-read at least three days before, so the offsite starts with discussion, not presentations.

A two-day annual planning offsite agenda

Two days gives you time to review, debate, decide and commit. A typical structure:

Leave real breaks and time outside. A packed agenda with no time to think is the most common reason planning sessions end without clear decisions. For more agenda formats, see our offsite agenda template.

How to run the sessions

• Separate discussion from decisions. Agree up front how decisions will be made, such as consensus or CEO decides after input.
• Use a neutral facilitator if the CEO needs to participate rather than lead the room.
• Force trade-offs. If everything is a priority, nothing is. Ask what the company will stop doing to make room.
• Write it down live. Capture decisions, owners and open questions on a shared screen, so everyone leaves with the same plan.
• Park off-topic issues in a visible list and assign owners before the end.

Annual planning template

Use this outline for the one-page plan you'll share after the offsite.

1. Where we are: [Three numbers that describe this year] and [the one lesson that shapes next year].
2. Where we're going: [The company's direction in one sentence].
3. Priority 1: [Priority] → Goal: [measurable target] → Owner: [name].
4. Priority 2: [Priority] → Goal: [measurable target] → Owner: [name].
5. Priority 3: [Priority] → Goal: [measurable target] → Owner: [name].
6. What we'll stop doing: [Projects, products or habits we're ending].
7. Resources: [Budget and headcount changes that support the priorities].
8. Risks: [Top two or three risks] → [how we'll manage them].
9. Review rhythm: Quarterly reviews on [dates]; owners report progress against goals.

After the offsite: making the plan stick

• Share the one-page plan within a week, first with leaders, then with the whole company.
• Cascade it. Each team sets its own goals that ladder up to the company priorities.
• Announce it at your kickoff. The annual kickoff is the natural place to share the plan with everyone.
• Review every quarter. Check progress, adjust goals and record what changed and why.

Where to hold your planning offsite

Choose a place that helps people think. Look for natural light, wall space for notes, a main room plus a breakout room, and good food. Distance matters too: far enough from the office that people stop checking in, close enough that travel doesn't eat into the agenda. For small leadership groups, a boutique hotel or a private house often works better than a large conference venue. Our leadership retreat venue guide covers what to look for.

Conclusion

Annual planning works best when it's treated as a focused event, not a series of meetings. Do the pre-work, hold a two-day offsite with time to debate and decide, limit the plan to three to five priorities with owners and goals, and share a one-page plan within a week. Then review it every quarter so the plan keeps guiding decisions all year. Offsite can find the right venue and handle the logistics, so your leadership team can focus on the plan.

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