Annual Planning That Drives Execution: A Practical Guide for Founders

Annual planning can leave every team with clear goals and still leave the company pulling in different directions.

The real work is agreeing on what matters most, how the priorities connect and what people need from one another to deliver. That’s what I mean by coordinated execution.

Over 25 years working with hundreds of teams, I’ve learned that the process of building the plan is as important as the plan itself. The conversations, questions and decisions create the shared understanding people need to execute.

For an early-stage company, this may involve the whole team planning together. As the company grows, the same process connects planning across multiple teams. In both cases, the work starts before the session and continues afterward.

1. Prepare the team before you plan.

Two to three weeks before the session, bring the participants together. Explain what you want to accomplish, walk through the agenda and give them time to prepare. Each agenda item should have a purpose and an outcome.

I ask each leader to think about the company’s future, their team’s priorities and their responsibilities. I also use a team survey to surface what’s working, what isn’t and what we need to talk about.

Give people space to unpack their thoughts beforehand. You’ll get more thoughtful answers and hear things that might otherwise stay unspoken.

Have leaders gather input from their teams. As the founder, bring in perspectives from your board, investors or advisors. You want the knowledge of the organization coming into the room.

2. Learn together, then map the climb.

Start by reviewing the past year. Look at the results alongside the survey responses. Where did you succeed? Where did you struggle? What did you learn that should change your approach?

Revisit roles and responsibilities, too. Growth creates gaps. Something that was clearly owned six months ago may now sit between two teams. Ask each leader whether they have the clarity they need to do their job.

These conversations shape the plan. If you jump straight into setting goals, you can miss the lessons that would make those goals more achievable.

I use a mountain analogy to help teams connect the pieces. You’re at base camp. Your mission is the North Star: why you’re making the journey. Your three-year vision is the farthest peak. Your one-year plan defines the summit directly ahead.

Define three to five objectives that describe success three years out. These might include the customers you serve, products you offer or markets you enter. Especially early on, that farther peak may be less defined. You’ll gain visibility as you climb.

Then work backward to three to five outcomes that would make the coming year successful. Agree on how you’ll measure success. Have each leader share their team’s proposed priorities so you can see how the work connects.

This is where cross-functional alignment matters. If sales wants to land enterprise customers, product may need security features and customer success may need a different onboarding approach. Can the teams support one another’s plans with the time and resources available? Work through those dependencies together.

Then define the first milestones: what must happen in the next 90 days? Objectives and key results, or OKRs, help make the plan specific. Talk through how you’ll achieve them. Agree on outcomes, owners, dates and who else needs to contribute. Make clear choices about what you’ll take on and what will wait.

3. Let the organization strengthen the plan.

I like to leave annual planning with a strong draft. There are still assumptions to test, dates to confirm and people to involve.

Have leaders take it back to their teams. Ask: What are we missing? Are these dates realistic? Where do you need another team’s help?

Some teams I work with call this “red teaming” the plan. You invite people closest to the work to challenge it and identify gaps before committing.

Bring that input back so the leadership team can refine the company plan. In a growing organization, this is where the team of teams model matters. Each team repeats the same planning process, building its own one-year plan and near-term OKRs aligned with the company’s direction. Teams then share their plans across functions to work through dependencies.

Before you call annual planning complete, ask people to explain the company’s one-year priorities, their part in achieving them and what they need from others to deliver. The gaps in those answers show you where more alignment is needed.

That’s how you prepare a team to climb together.

Jeff James Martin is the founder and CEO of Collective Genius, an organizational execution company that helps founders and leadership teams execute better together. He is the creator of Peak OS, the company’s system for connecting direction, alignment, execution and learning across the organization, and author of Peak Teams.