It's football season, and I recently finished the docuseries on Nick Saban, the legendary former University of Alabama football coach who led his teams to seven national championships. Love him or not, one thing comes through in every episode:
Saturday's game is largely decided long before kickoff.
Everyone knows the X's and O's matter. What struck me was the depth of the process underneath them. The film study, the practice reps, and the weekly discipline most fans never see.
Strategy works the same way.
Right now, leadership teams are putting 2027 strategic planning on the calendar.
That's a good sign.
The challenge comes after the planning session.
There's a business to run, people to lead, customers to serve, and no shortage of priorities competing for attention. Even with the best intentions, the strategic plan can start to function a little like artificial turf: lay it down, admire how good it looks, and expect it to hold up all season.
But real grass needs tending. There's a grounds crew out there every week, watering, mowing, and repairing the spots that took the hardest hits.
Strategy needs that same attention. That's the difference between having a strategic plan and keeping a strategy alive.
When every division is winning and the organization isn't
Early in my career leading strategy, I remember how every leader at the table was driving hard in their own direction, and all of it was good work. That's what made the problem hard to see.
The way I described it then: we were building one muscle at a time. Strong biceps all around. Meanwhile we were trying to run complicated plays, and we were pulling hamstrings left and right, because no one was caring for the whole body.
You could see it most clearly in the functions everyone shared. Technology was the obvious example. That wasn't because the team wasn't excellent. It was because in a digital age, every division needed them. They were stretched so thin that the work that mattered most to the whole organization was getting choked off by everything that mattered to each part of it.
Frustration was growing. And no one was wrong, exactly. Each leader was doing what good leaders do for their own area.
The plan wasn't the only problem
We could have refreshed the plan. We could have updated the goals, reformatted the document, and presented it to the board. It would have looked fine.
What we actually needed was a different way of working together. So we overhauled the calendar. We set aside dedicated, regular time to sit together, understand what each of us was carrying, and work through the trade-offs. Not to wrestle one another to the ground. To wrestle the constraints to the ground.
That's harder than it sounds.
It asks leaders to hold their own division's hopes a little more loosely for the sake of the whole.
It asks the organization to define outcomes and impact, not just outputs.
And it asks the organization to resource the strategy, not just approve it.
What came out of that work was more than a better plan. It was strategic clarity: a shared understanding of where we were going, the discipline to choose, and a way to decide when good priorities competed.
A plan tells you what you intend to do.
Clarity tells you what to do when something comes up that the plan didn't anticipate.
"We already did a strategic plan two years ago"
Good. Then the question isn’t whether you have a plan. It’s whether you have a grounds crew.
Most plans don’t fail in the planning session. They fade in the months after, when the room empties, the calendar fills back up, and no one is responsible for tending what was decided. Then priorities collide, and without a shared way to decide, the loudest voice wins.
A strategic plan can look beautifully finished on paper. But strategy isn't finished when the planning session ends. That's when the real work of tending it begins.
Clearing the path for 2027
If 2027 planning is on your calendar, the work starts now, before anyone writes a goal. Here are three questions to bring to your leadership team this week:
Where are we building one muscle while straining another?
Which shared function is carrying more than it can sustain?
What trade-off keeps getting deferred because every option is worthwhile and we don’t have a shared way to decide?
If those spark a lively conversation, or an uncomfortable one, pay attention. They’re a starting point. The deeper work comes after: turning what you uncover into choices your team can stand behind, and building the rhythm that keeps those choices alive all season.
That’s the work I do with leadership teams. Some are starting fresh with a strategic plan. Some need strategic renewal for a plan that’s lost momentum. Others need Strategic Growth Advisory to build the system that keeps strategy alive between planning cycles.
Wherever you are, the goal is the same: clarity your whole team can act on.
If you’re clearing the path for 2027, let’s talk about what it will take.
A confidential conversation can help clarify the larger system around it—and what kind of support would be most useful.
Cassandra Shepard is the founder of Shepherd + CO, a boutique strategic advisory firm. She works with senior leaders navigating the intersection of enterprise strategy and advanced leadership. www.cassandrashepard.com