In these last months of the year, our strategic facilitators have been busy. Many leadership teams are in the middle of three-day offsites and locking in their strategic plans before the calendar flips. This end-of-year push makes sense. There is something powerful about closing one chapter with clarity and entering the next with a plan.

But not every company plans in December. Some of our engagements happen in January or February. It is not too late to create a strong, aligned, effective strategic plan for 2026.

What matters far more than when you plan is how you plan.

If you are wondering whether you are truly set up for a successful planning process, here are the questions that matter most.

1. Do You Have a Proven System, or Just an A la Carte Menu?

Many CEOs tell us the same thing. They know strategic planning is important, but they are not happy with the outcome. The plan feels vague. Alignment is shaky. Momentum fades quickly.

That usually points to the system itself.

Ask yourself:

• Have we used this approach before?
• Did it produce clarity, alignment, and results?
• Did it actually change how we operated?

If the answer is no, repeating the same process will not suddenly deliver a better plan. You already know the adage of doing the same thing again and expecting a different result. A proven system gives structure to hard conversations, forces real tradeoffs, and creates accountability. Without that, planning tends to become a long discussion that feels productive but does not change much.

2. Are You Willing to Set Aside Real, Dedicated Time?

One of the biggest predictors of a strong strategic plan is how seriously you treat the time itself.

We recommend at least two full days. One day to surface ideas, pressure-test assumptions, and define potential goals. Then time away from the room. Sleep on it. Come back with clearer thinking to make it solid.

Trying to build a strategic plan in short bursts, pulled from regular meetings or squeezed between operational demands, sends a message: Strategy is important, but not important enough to protect.

What you get out of strategic planning is directly tied to what you put into it. Dedicated time creates space for better thinking. Anything haphazard tends to produce a haphazard plan.

3. Are You Bringing in Your Executive Team Thoughtfully?

One common fear CEOs have is this. What happens when everyone shows up with opinions, frustrations, and competing priorities, and there is no structure to contain it?

That is why we believe strongly in pre-work.

Before the session even begins, teams benefit from stepping back and reflecting individually. If your executive team had the CEO seat, what goals would they set for the year? Where do they see the biggest opportunities and risks? What questions do they want answered?

This kind of preparation changes the room. It gives you insight into how your team is thinking. It surfaces alignment and misalignment early. It allows you, as the CEO, to prepare for the conversations that actually matter.

It also signals respect. You are not asking people to react in the moment. You are asking them to think.

4. Are You Clear on Your Own Vision as the CEO?

No strategic planning process can compensate for an unclear CEO vision.

Before you walk into the room, it is worth spending time alone with some hard questions:

• Where has the company been?
• Where are we trying to go?
• What does the next three years need to look like?
• How much growth do I actually want, and where do I believe it will come from?

Clarity here does not mean rigidity. It means direction. When the CEO has a grounded point of view, the team can engage more honestly and productively.

5. How Will You Keep Strategy Alive After the Offsite?

A plan that lives only in a deck or a document is not a strategy. It is quickly a memory.

The final and often most overlooked question is this. What will keep the momentum going?

Clear goals are only the starting point. You need agreed-upon measures, ownership, and a governance rhythm that keeps strategy on the agenda throughout the year. Strategy should remain part of every executive’s job, not something that fades once people return to their functional roles.

When strategy is revisited regularly, pressure-tested, and adjusted as needed, it becomes a living system rather than a one-time event.

The Bottom Line

If you have not locked in your strategic plan for 2026 yet, that does not mean you are behind. It just means you have an opportunity to do it better.

Whether your planning happens in December, January, or February, the goal is the same. A clear direction. Real alignment. And a plan that actually guides where the business goes.

It is not too late. What matters is choosing an approach that gives your strategy a real chance to succeed.

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