Annual Planning for Founders: The Decisions Only You Can Make

There’s a moment in every annual planning session that reveals the truth about our role as founders. The ideas are flying, the team is fully engaged, the whiteboard’s packed with ambitious goals. And then the room looks to us. Not because we're running the meeting, but because a call needs to be made. There's a boundary to set, a path to commit to. And it becomes clear: There are decisions only we can make.

In my last article, we dove into high-impact annual planning — what it looks like when great companies align for the year ahead. How alignment, not perfection, is the real goal. Because when it comes to annual planning, it’s less about nailing predictions and more about setting direction, building trust, and creating clarity throughout our organizations.

Now, we’re digging deeper into the founder’s role in that process. Because while planning is a team sport, there are some plays only we can run. It’s the kind of work that rarely fits neatly into a checklist, yet it shapes the trajectory of everything that follows.

The fact is, our role can't be outsourced. We can (and should) empower a strong leadership team. But we can’t fully entrust the vision to a facilitator. We can’t let someone else decide which trade-offs to make. And we definitely can’t delegate the responsibility of aligning strategy with the long-term direction of the company.

Our teams are looking to us to make the hard calls, to name what matters most, and to bring clarity when the path forward is unclear. So let's talk about the parts of annual planning that sit on our shoulders as founders.

The Founder’s Role in Annual Planning

I’ve seen what happens when founders step too far back during annual planning. Smart, capable teams fill the time with well-intentioned effort. They leave the session with a long list of priorities but not enough focus. Six months later, they’re busy but not aligned. That’s the problem when there's too many goals and not enough traction.

That’s why there are a few responsibilities I’ve learned never to delegate. It’s not about control or micromanagement. It’s about owning the calls that require our perspective, the ones that give shape to everything else the team builds.

Here are five elements of annual planning that need to sit with us as founders:

1. Revisiting and refining Focus Filters: Your Forever Agreements and the other Focus Filters help your team decide what deserves attention. They connect the vision to the real world — to decisions about time, money, and effort. Every planning cycle is a chance to revisit them. If they’re vague or outdated, your people end up prioritizing the wrong things. But when they’re clear, the whole team can move faster with fewer second guesses or fire drills.
2. Deciding when to say no, even to good ideas: It's easy for every issue or pitch to sound like a priority during annual planning. But if you say yes to all of it, you end up diluting the work that really matters. This is where your judgment counts. What needs to happen immediately, and what can be a long-term issue to address later? Cutting something doesn’t mean it isn’t valuable. It just means it isn’t essential right now.
3. Connecting the plan to the vision: Even in companies with a strong vision, the day-to-day can slowly take over. Planning turns into an endless checklist. Your job is to bring the bigger picture back into focus. To ask: Are we still heading where we said we’re going? Are we still building what we set out to build?
4. Seeing (and naming) what doesn’t fit: As the plan comes together, some things just feel off. Goals that pull in different directions. Rocks that sound important but don’t really move the company forward. Decisions that don't feel like they reflect your values. You don’t need to fix everything, but you do need to name what’s misaligned and slow down before your team starts moving in the wrong direction.

When you own these parts of the process, you give your team what they need most: direction, intentionality, and confidence. You don’t have to run the whole meeting or solve every issue. But you do have to define what matters. That’s how you turn a long list of goals into a plan people not only believe in, they follow through on.

At Ninety, we’ve seen how foundational this part of the work can be. That’s why we built a set of annual planning resources to help founders and leadership teams run focused, high-impact sessions with confidence — the kind that turn vision into real, measurable progress.

How We Show Up Matters

Annual planning isn’t just about what ends up in the plan. It’s about the energy in the room while the plan is being built. That’s the momentum our teams will carry into Q1, and whether we realize it or not, that energy often starts with us.

When the team hits a tough decision — when trade-offs need to be made, when there’s disagreement about what’s realistic, or when something just feels off — it’s our presence that steadies the process. The way we listen, reflect, and make the call when it’s time.

Sometimes that means slowing down a conversation that’s moving too fast. Sometimes it means calling out the thing no one’s naming. Sometimes it’s as simple as saying, “This is hard, but here’s what I believe we need to do.”

We don’t need to be the loudest voice or the smartest strategist in the room. But we have to show up with clarity and conviction, especially when the path forward isn’t obvious. Because planning is more than operational. It’s cultural. It’s where our team learns how we make decisions, what we value, how we weigh risk, and how we stay true to the vision when things get complex.

That’s why our presence and the energy we bring shapes more than the plan. It shapes the year that follows.

Strategic planning is worthless, unless there is first a strategic vision.

John Naisbitt

Holding the Standard

There’s a weight to being the founder in an annual planning session. We’re not just another voice in the room — we’re the ones who frame what’s possible and what’s not. We help shape the boundaries of ambition while keeping everyone grounded in reality.

That balance matters. Push too hard, and the plan becomes a fantasy. Play it too safe, and progress stalls. The real work is holding both truths at once: the drive to build something extraordinary and the discipline to do it well.

Our teams take their cues from us. If we show up prepared, curious, and focused, they’ll rise to meet that energy. If we’re distracted or defensive, they’ll feel that too. We’re modeling not just how to plan, but how to think. How to stay honest about where we are and confident about where we’re headed.

Leadership in these moments isn’t about talking more. It’s about listening better. It’s about knowing when to challenge, when to encourage, and when to pause long enough for the truth to surface.

That’s one of the most important roles we have in planning: To hold the standard for ambition, for alignment, and for what high-performance looks like. When we do that well, everything that follows has a stronger foundation.

Where It Really Matters

When we step into annual planning as founders, we’re stepping into a session that only comes once a year, but its impact lasts far beyond it. The conversations we lead, the questions we ask, the boundaries we draw, they all shape the culture of how our teams work together.

Our role isn’t to dominate the session or to have every answer. It’s to bring steadiness and perspective. To hold both vision and reality in the same hand. To remind the team why we’re building what we’re building. And to be sure the plan we leave with actually reflects that truth.

Annual planning has a way of revealing who we are as leaders. It tests our patience, our clarity, and our discipline. But it also gives us a chance to lead in the purest sense — to align, simplify, and name what matters most.

So as you head into your next annual planning session, remember this: Your team doesn’t need perfection. They need you to show up, listen deeply, and lead where only you can.

Ready to put this into practice? Check out Ninety's annual planning resources to help your leadership team run a high-impact planning session with clarity and confidence.