4 Steps to Turn Your Annual Plan into Real Progress

​​The annual planning session is done. You’ve made the hard calls, set the goals, and aligned your Senior Leadership Team (SLT). You’ve clarified the direction for the year ahead and, most importantly, why it matters. Now comes the part that separates great companies from their competition: execution.

In my last article, we focused on our role as founders and/or CEOs in the annual planning process — the judgment calls only we can make, the energy we bring, and the standards we set. Now, let's talk about what happens next. Because building the plan is only the beginning.

The best companies don’t treat annual planning as the finish line. They treat it as the starting gate. What happens in the weeks and months after determines whether the plan becomes reality or loses traction.

Because that’s when the real test begins: turning shared goals into consistent action. So let’s walk through four practical steps you can take to bridge the gap between annual planning and progress.

1. Start with a Strong State of the Company Meeting

The first step in turning the plan into progress is making it real for everyone. That’s why one of the most important things you can do once your annual planning session has wrapped is hold a State of the Company Meeting. It’s the moment when your SLT’s decisions turn into shared direction throughout the organization.

At Ninety, we walk our entire team through how we performed against last year’s goals — what we hit, what we missed, and the lessons we learned. We share any updates to our vision, Forever Agreements, or other Focus Filters. We roll out the new 3-year and 1-year goals, along with Q1 Rocks. In essence, we’re saying "Here’s where we’re going. Here’s how we’re going to get there. And here’s how your work contributes."

And then, we open it up. Because trust doesn’t just come from telling the truth. It comes from inviting conversation. When people understand not just the what, but the why, and when they see their leaders modeling transparency, they’re far more likely to own their part of the plan.

You don’t need a polished script or a detailed agenda. You just need clarity, presence, and a commitment to making this more than a one-way presentation. When done well, the State of the Company sets the tone for how the whole organization shows up in the year ahead.

2. Cascade the Goals

This is where a lot of companies stumble. The SLT builds a strong plan, they share it with the entire company, and then the momentum stops. Here’s the thing: Direction doesn’t cascade on its own. It has to be translated.

Each department needs to hold its own annual planning session after the SLT's. These don’t have to be elaborate. But they do need to answer one essential question: How does our department contribute to the company’s goals this year?

That contribution happens through departmental Rocks. Just like the company, each team should revisit the purpose, determine meaningful Rocks that directly connect to the company’s goals, and assign each one to a team member. Done well, this creates alignment and ownership.

You’ll know the process is working when someone at any level can say, “Here’s how my work this quarter supports our 1-year goal of [X].” That’s when the plan gets internalized. Why? Because it’s now something each person helped shape, not a directive just handed down from leadership.

As founders and/or CEOs, it might be unclear how involved we should be in this part of the process. My answer: Stay close, but don’t control it. Our job is to ensure each team understands the vision and feels empowered to chart their own course within it. If every Rock has to come from the top, you’re not building a resilient company. You’re just managing a business.

3. Build Systems for Execution

Execution doesn’t run on pressure. It runs on consistent systems.

One of the biggest realizations many of us face as our teams grow is that consistent follow-through isn’t about setting high expectations. It’s about building the structure and cadence that keeps goals visible and work moving forward.

That’s where Weekly Team Meetings come in. These aren’t just check-ins — they’re working sessions. Every week, each of your team's reviews their Rock progress, checks key metrics, and solves real issues. These meetings create a steady loop of accountability and momentum.

Then, at the end of each quarter, reset with Quarterly Planning Meetings. That’s where every one of your teams reviews their Rocks from the previous quarter, reflects on what worked and what didn’t, and identifies what needs to change. Then, it's time to set the next round of Rocks. This helps teams stay focused, adaptive, and in sync with the bigger picture.

Without consistent systems, even the best plans get buried beneath day-to-day tasks. But with them, progress compounds.

4. Use Data and Dialogue to Stay on Track

Even with clear 3-year and 1-year goals, quarterly Rocks, and solid systems, things can go off track. Priorities shift, surprises emerge, and some people may struggle to keep up. That’s not a sign the plan failed — it’s just a sign the system needs to adapt.

This is where visibility and trust matter most.

First, we need data up and down the organization. That means more than just numbers — it means having Scorecards that track the right KPIs week after week, show how they’re trending, and flag when something’s off. Good data gives our teams a shared understanding of what matters, where we’re winning, and where attention is needed.

But data alone isn’t enough. We also need dialogue, the kind that turns talk into action. That means creating space in Weekly Team Meetings for people to name issues, ask for help, and raise concerns. When our teams feel safe bringing up what’s not working, we can address issues while they’re still small.

The best teams don’t avoid problems. They see them coming and solve them together. Over decades spent both building and coaching companies, I’ve learned that consistent execution only scales when people believe in the plan and see how their work contributes to it.

That’s the role of data and dialogue in execution. They make progress visible, and they build the trust that keeps people engaged, even when (especially when) the plan needs to change.

Plans are only good intentions unless they immediately degenerate into hard work.

Peter Drucker

Keep the Plan Alive

Our plans are only as strong as the attention we give them.

Too many companies finish annual planning and treat it like a document to be filed away until next year. Great companies keep theirs alive, week after week, quarter after quarter, year after year. They talk about it in meetings. They revisit it in 1-on-1s. They celebrate progress and make adjustments when needed. Planning becomes part of the culture.

So as you move from planning into execution, remember this: You’ve already done the hard work of setting direction. Now comes the daily discipline of staying true to it. Host your State of the Company, cascade the goals, build consistent systems, and use data and dialogue to keep the plan visible and real.

Because when your team sees that the goals you set actually shape how you work — and that the progress you make really matters — that’s when they execute. And execution is what turns good plans into lasting progress.

Ready to put this into practice? Check out Ninety's annual planning resources to help your leadership team not only run a high-impact planning session, but execute the plan with clarity and confidence.