Most CEOs Will Start Planning 2026 Too Late. Again.
You will feel so much better going into the holidays if you already have a handle on your company's plan for next year.
I have space later this year to work with 2–3 CEOs and their teams on intensive 2026 strategic planning.
If you are interested in taking one of these spots, let’s talk this week.
I called this Substack “Managing the Future” because thinking ahead is inherent to the work of the CEO.
More so than any other corporate role, the CEO must keep their eyes on the horizon.
They must continuously monitor on-the-ground reality while looking forward to the desired state they want to achieve months, years, even decades from now. They have to ask, Will what we’re doing now get us to where we want to go?
It’s still a couple of months until the first strains of Christmas music hit your eardrums, but it is not too early to begin thinking about 2026. The future is coming fast, and you will feel so much better going into the holidays if you have a handle on your company’s plan for next year.
Starting in January Is Too Late
I’m a big fan of starting annual planning early, and not just because it personally helps me feel more prepared. It’s also just really hard to get people together later in the year for an offsite, which is a critical piece of the puzzle.
If you don’t at least get a planning session on the books now, it will be October and the scheduling conversations will go like this:
“Q4 is crazy with this acquisition going on. Should we wait?”
“I've got a procedure that week and I’ll be out the next.”
“We're in Europe then."
Sound familiar?
Before you know it, you're staring down January 1 with no strategic plan, scrambling to get your executive team together while everyone’s still shaking off their holiday food coma.
Your business is now like the person who decides to get healthy in January but spends December indulging, only to find themselves feeling discouraged and behind the eight ball when the new year arrives.
Strategic Planning Isn't a Solo Sport
As CEO, you might be tempted to think you can just lock yourself away and craft the perfect plan for 2026.
But as I’ve written about before, strategy thrives on many minds. Just as ten chess grandmasters analyzing a single board will outperform any individual player, your executive team’s collective intelligence will produce a stronger strategy than you could create alone.
This means your strategic planning can’t happen alone in your ivory tower or through haphazard hallway conversations or in a meeting where half the team is missing or checked out.
You need your leadership team physically present and mentally engaged, bringing their perspectives to bear on your biggest challenges.
The Compound Effect of Early Planning
When you start your strategic planning process in late summer or early fall, you unlock several advantages that become impossible to replicate later:
Resource availability. Good facilitators book up months in advance. Quality offsite venues fill their calendars early. Wait until November, and you're stuck with whatever’s left over or trying to do serious strategic work over Zoom.
Implementation time. A plan created in November gives you time to begin early implementation, test assumptions, and course-correct before the new year begins. A plan created in January or February starts you behind schedule immediately.
Organizational discipline. Early planning forces the kind of organizational discipline that separates high-performing companies from the rest. It signals to your entire organization that strategic thinking is scheduled, protected, and prioritized. Getting seven busy executives in the same room for two to three days requires the same discipline as losing weight. Everyone knows what to do, but execution trips people up.
So, block the dates of your planning offsite now. Not next month, not when “things calm down.” And communicate the stakes to your team. They need to understand that this planning session will shape everything your company accomplishes next year.
For those ready to break the cycle of starting too late, I have space to work with 2–3 CEOs and their teams this year on intensive 2026 strategic planning. The quiet months before the year gets crazy are exactly when the most important work gets done, even if it’s simply carving out the time before everyone’s calendar turns into a war zone.
If you’d like to explore a facilitated strategic planning session for your team, book a 30-minute session with me and we can discuss.
The future is coming whether you're prepared or not. Now is the time to get ahead!