Every fall, leadership teams sit down to plan the year ahead. Here's how operators build annual plans that people actually execute, from the prep work to the weekly rhythm that keeps the plan honest.
This piece is adapted from an Operators Guild Focus Session on annual planning, featuring Jeff Martin, founder and CEO of Collective Genius, creator of PeakOS, and author of Peak Teams*. Jeff has spent more than 25 years helping founders and leadership teams plan and execute together, at companies ranging from a handful of people to more than a thousand. Focus Sessions are small-group, member-only conversations where operators pressure-test decisions, share systems, and surface the realities that rarely show up in frameworks or playbooks.*
If you want access to sessions like this, including the recordings, the working examples, and the community behind them, you can apply to join OG.
Sometime in the next few weeks, a lot of leadership teams will gather to plan the year ahead. Some will leave with a plan people actually use. Others will leave with a well-formatted deck that stops mattering by February.
Ask operators what annual planning is for, and the answers come quickly — alignment, clarity, focus, measurable goals, commitment. All true. The more useful framing ties them together. The purpose of annual planning is coordinated execution, getting the whole organization moving in the same direction and staying there as conditions change.
That framing matters because execution is what separates companies competing in the same market. Startups have a reputation for productive chaos, but the teams that win tend to be the most organized ones. They know where they're going, who owns what, and how they'll adjust when the plan meets reality.
Why most annual plans fall apart
The failure patterns are familiar to anyone who's sat through a planning offsite. Not enough prep. Unrealistic expectations. A plan handed down from the top. Alignment that looked real in the room and evaporated once everyone went back to their own teams.
Most of those problems trace back to five gaps:
- No clear structure. No methodology, a thin agenda, and no agreement on what the session should produce. The opposite problem exists too: systems so elaborate no one can keep them running.
- No shared clarity. People aren't aligned on where the company is going, what needs to happen, how, by whom, and by when.
- Weak collaboration. The plan comes from a small group instead of drawing on what people across functions actually know.
- No operating rhythm. Nothing turns the plan into weekly action, so it's outdated before execution starts.
- Planning treated as a precursor to the work. Building the plan together is part of the work, and teams that skip that process skip the alignment it creates.
Underneath all five sits the same issue. People across the company may be working hard, but they aren't working from the same picture.
Start at the North Star and work backward
A useful way to picture a shared plan is a team at base camp looking out at a range of peaks. Before deciding which way to go, you work backward from the farthest point on the horizon.
The mission is the North Star. It explains why the company exists and why the team is making the climb at all. It doesn't need two hours of debate every year, but it's worth 10 to 15 minutes to confirm it still holds. Some people on the team will care about it deeply, and it works as a gut check for everything else in the plan.
The 3-year vision puts a stake in the ground. Treating annual planning as a strictly 12-month exercise is a common mistake. Three to five objectives that describe success three years out give every team a destination, and the best people want to work on teams that know where they're headed.
The 1-year plan is the peak directly ahead. At the leadership level, it's about five objectives, metric-based or not, that define a successful year. Then it cascades. Sales, marketing, product, engineering, and every other function builds its own one-year plan of three to five objectives anchored to the company's. That team-of-teams structure works best when every team can see what the others committed to.
OKRs are the milestones on the way up. Over 90 or 180 days, objectives define what the team will accomplish and key results define how. Add owners, dates, and a RACI to each key result, and the plan answers who and when as well.
When all four layers are in place, the organization shares a clear view of the why, where, what, how, who, and when. That clarity rarely comes from a CEO gathering input and presenting a polished deck. It comes from the team building the plan together.
Planning starts two to three weeks before the offsite
The session that goes on everyone's calendar is only the middle of the process. The prep call happens two to three weeks earlier.
That call covers the methodology and any tools the team is new to, walks through the agenda, and assigns prep work. Leaders also come in with a draft of the 3-year vision and the objectives they think matter most, both for the leadership team and for their own function. And once a year, it's worth reviewing roles and responsibilities as a group. Teams are routinely surprised by the gaps, overlaps, and confusion that turn up.
Learn first, then plan
The team leader (the CEO, for a leadership team) reflects on the past year and sets a theme. The group shares expectations for the session, reviews roles, digs into the survey results and last year's metrics, and works through the most pressing open topics. Only then does it revisit the mission, confirm the 3-year vision, and build the one-year plan, with each functional leader sharing their team's top objectives so everyone understands what the others are working on.
Day two turns those objectives into OKRs, and this is where teams tend to struggle. Some load key results with metrics and little else, which falls apart quickly. A better test for any key result is to ask what it looks like when it's done. Key results are where the team finally talks through how an objective will get achieved, which is the conversation most planning sessions skip.
Leave with a strong draft, then pressure-test it
The goal at the end of an annual session is a strong draft. Some owners and dates will be hard to pin down in the room, and that's fine.
From there, leaders take the draft back to their teams and the board for feedback. Some teams call this red-teaming the plan: distribute it and invite people to challenge it. The leadership team refines it together at the next weekly meeting, then the next layer of teams runs the same process for their own plans.
Smaller companies might keep the process at the leadership level for the first year and push it down once executives are comfortable with it. Larger ones can cascade it through several layers. The tools work the same way for a 25-person startup and a division inside a 2,500-person company.
Plan for the plan to change
Every operator has watched a good plan meet reality and lose. Customers shift, markets move, priorities change, and new information arrives mid-quarter. The better question is how the organization responds when that happens, and the answer is an operating rhythm.
The rhythm runs on a simple cycle: learn, adapt, plan, act, repeat. It's the same loop behind the scientific method and Deming's work on continuous improvement. Every company starts out running it, usually inside one founder's head. As the company grows, dozens of people run their own versions, and cadence is what pulls them back together:
- Annual: the full cycle, from business review to new OKRs
- Semi-annual or quarterly: a reset for leadership teams and faster-moving sub-teams
- Weekly: the same loop at a smaller scale, where the triage list lives
- Daily: standups for product and engineering teams that need them
The gap between what a team intended and what actually happened is execution drift. Some drift is inevitable. The goal is to spot it early and correct it together.
Teams that run the cycle consistently start to see the opposite effect, execution lift. Each loop makes the team a little better at the next one, and those gains compound. Drift pulls an organization away from what it set out to do, and lift moves it closer.
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