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This time of year, I see the same tension surface for founders and leadership teams again and again. The calendar’s turning, the pace is picking up, and deep down everyone knows it’s time to pause and plan. But there’s also resistance because the plan won’t be perfect. Markets inevitably shift, priorities evolve, and our teams will need to adapt along the way.
So why plan at all?
Because high-impact annual planning isn’t about nailing predictions. It’s about alignment, prioritization, and focus. It’s about creating clarity — first for the leadership team, then for the entire company. It’s a discipline that allows your organization to move forward with intent, even as it navigates complexity and change.
Great companies don’t stumble into lasting success. They earn it through deliberate effort and consistent reflection. When done right, planning becomes one of the most powerful feedback loops in your company. It’s how you compound progress and strengthen the culture.
In this article, I’ll walk you through what high-impact annual planning looks like: when it matters, how to do it, what to expect, and why it’s one of the most valuable investments you can make in your company’s future. If you’re serious about building a productive, humane, and resilient organization, this is the foundation.
Annual Planning Starts with Stage Awareness
Before we dive into what annual planning looks like, let's get clear on when it’s essential. The truth is, not every company needs it from day one. It comes down to your Stage of Development, and I often tell Stage 1 and even early Stage 2 companies to hold off. Why? Because annual planning doesn’t make sense when you haven’t even locked in product-market fit.
By Stage 3, when you're looking 1–2 years ahead and building a real leadership team, annual planning becomes a core discipline. And if you're in Stage 4 or 5, which means you’re looking 2–10 years down the road, it's nonnegotiable. You simply won't scale without it.
And I'm not speaking theoretically. In my four decades spent investing in and coaching hundreds of leadership teams, I've seen firsthand what happens to organizations that avoid annual planning, and it isn't pretty. You lose alignment, you chase shiny objects, and you stop compounding the progress you worked so hard to earn.
But when you do embrace it, annual planning gives you something powerful in return, especially in Stages 3 through 5. It gives you clarity about where you’re going. Confidence in how to get there. Accountability for every person in every Seat. And perhaps most importantly, the peace of mind that comes from knowing your team is truly aligned. That’s the kind of momentum that grows over years, not just quarters.
What It Looks Like When Done Well
Annual planning is more than a meeting. It’s a working session meant to bring your entire organization into alignment. You step back, take stock of the bigger picture, and refocus on what matters most. The outcomes aren’t abstract ideas or hopeful ambitions. They’re structured, time-bound goals that guide decision-making at every level of the company.
I recommend connecting three time horizons:
- 3-year goals: These evolve each year. They roll forward, so each annual cycle brings you one year closer to your long-term Compelling and Audacious Goals.
- 1-year goals: These remain fixed throughout the year. Yes, the market might change, but you earn strategic discipline by staying focused. Shifting them mid-year should be rare.
- 90-day goals (aka Rocks): These are the steps that keep you on track quarter by quarter. The key is making them SMART so they're clear, measurable, and meaningful.
The reality is every now and then you get into the first quarter of a new year and you may want to change your annual goals. But one of the ways you know you have a good leadership team is if your annual goals don’t change and you deliver on them consistently. That doesn’t mean hitting every single goal. Perfection isn’t what we’re striving for here. You have a solid team if you’re consistently hitting 80–90% of your annual goals.
And yes, done well, these plans cascade. Departments, teams, and individual contributors build aligned goals based on what the company is committed to. That’s the magic. That’s how everyone from the C-suite to the newest team member sees how their Work contributes to the whole.
Two Days, Done Right
Our annual planning process unfolds across two dedicated days with the Senior Leadership Team. Not a week of scattered meetings or a rushed single-day session. Two focused, structured, immersive days. Here’s the general flow:
Day 1
- Check in personally and professionally with your team. Set expectations for the session.
- Reflect on the past quarter and the past year. Grade your company’s performance honestly. At Ninety, we use traditional letter grades for this (A, B+, C–, etc.).
- Review your current vision, including your Forever Agreements, Core Values, ICP, and Compelling Why.
- Invest time in trust-building exercises that deepen the connection among your team (usually a couple of hours).
- Conduct a thorough SWOT analysis.
- Identify and prioritize key topics (things we need to talk about before updating 3–year and 1–year goals) and long-term issues.
At the end of Day 1, go out for dinner with your team. Celebrate the progress you made and bond as humans.
Day 2
- Discuss any key topics from Day 1, and add any new issues that need to be addressed.
- Reconfirm or refresh your 3-year goals. Assess whether you’re still on track to reach your Compelling and Audacious Goals.
- Set your 1-year goals (aim to keep the total under seven). Make sure these goals will keep you on track to hit your 3-year goals.
- Establish and assign Rocks for Q1.
- Address remaining issues.
- Close with a review: Did the session meet everyone’s expectations? Was the meeting productive? Rate it on a scale of 1–10.
At Ninety, we’ve seen how powerful this process can be — and how often it gets overlooked or rushed. That’s why we created a set of annual planning resources designed to help you facilitate these sessions with confidence, whether you’re a first-time founder or a seasoned coach. They’re practical, battle-tested, and available to any team committed to doing this well.
We owe it to our company to all work together to get on the same page — where we are, where we’re going, and how we’re going to get from here to there.
The Importance of Trust
None of this works without trust. Not just general camaraderie. I’m talking about deep, character-, competence-, and connection-based trust. In every annual session I lead, I make space for it on the first day. Sometimes that means structured exercises where we give each other feedback across the dimensions of connection. Sometimes it’s simpler. But it’s never skipped.
You can have the best tools, the clearest vision, and the sharpest team, but if you don’t trust one another, you won’t align. And if you’re not aligned, your plan won’t carry weight, no matter how polished it looks.
But trust doesn’t stop with the leadership team. That’s why every annual session ends with a State of the Company Meeting. We share what we achieved (or missed) last year, any updates to our vision or Forever Agreements, our new 3-year and 1-year goals, and our Q1 Rocks. Then we take questions, invite discussion, and let the clarity spread throughout the organization.
From there, departments and teams hold their own Annual Planning Meetings. They define how their work contributes to the company’s goals and establish their own Rocks. That’s how trust and clarity cascade together to create alignment throughout the company — and how you build a truly high-trust culture.
And Then You March
When I think about the companies I’ve coached and the ones I’ve helped build, the difference between those that fully embrace annual planning and those that don’t is unmistakable. The teams who make it a discipline don’t just hit more goals, they grow stronger together.
Hitting 80–90% of your Rocks quarter after quarter is a sign that your planning muscle is strong, that your team is executing, and that you’re scaling in a healthy, sustainable way. The founders who commit to this process year after year feel different. The work becomes more focused. The energy feels steadier. The results compound. And over time, that steady, deliberate progress is what leaves a lasting legacy.
Annual Planning isn’t a luxury. It’s not a nice-to-have. It’s the foundational discipline of great companies. It’s the moment each year when you choose to align, focus, and invest in the future you’re building together.
It starts with one simple commitment: Take the time to plan well. It will change everything.
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.
