Every leader knows how to build a plan.
We set goals.
We identify priorities.
We map out what we want to accomplish in the year ahead.
And if you’re like most leaders I work with, you’ve probably already done that work for next year.
But here’s the part we don’t spend nearly enough time on:
What happens when the plan meets reality?
Because it will.
Not everything will go smoothly.
Not everyone will buy in.
Not every part of your plan will land the way you expect.
And that’s not failure.
That’s leadership.
Years ago, as a superintendent, we made the decision to move toward project-based learning across our district.
We brought in strong professional development.
Teachers and administrators were trained.
Time was given to design meaningful projects.
I was in the training myself. I believed in the work. I knew it was the right direction for our students.
And then the school year started.
Some teachers embraced it. They collaborated, sought feedback, invited others into their classrooms, and created incredible learning experiences.
Others didn’t.
Some struggled to see how it fit.
Some said, “I already do this—I just call it something else.”
Some quietly chose not to implement it at all.
Same training.
Same expectations.
Very different results.
That’s when I realized something important:
This wasn’t a planning problem.
It was a leadership problem.
If your plan only works when everything goes right, it’s not a strong plan.
The question isn’t whether things will get messy.
The question is:
Have you planned for that moment?
Looking back, there are several things I would do differently—not in how we built the plan, but in how we prepared for the reality of implementation.
When implementation begins to break down, most leaders don’t see it right away.
Not because they don’t care—but because they don’t have a way to see it.
We didn’t have a shared system to track what was happening:
And because of that, the work became optional for some.
If the work matters, it has to be visible.
Because what isn’t visible… rarely gets done.
We invested in great professional development.
But then we moved on.
And what I’ve learned since is this:
Training starts the work. It doesn’t sustain it.
When the year gets busy—and it always does—new initiatives don’t fail because people disagree with them.
They fail because they get crowded out.
If I could go back, I would:
Because without that support, even the best ideas fade.
This idea of building support before you need it extends beyond professional learning—it applies directly to how we support students as well.
If you already know that some of your students will need additional help next year—whether that’s intervention, acceleration, or targeted academic support—it doesn’t make sense to wait until the school year begins to figure that out.
That’s where partners like HeyTutor can make a real difference.
HeyTutor provides high-dosage tutoring in Math and ELA, both in-person and online, with trained tutors they recruit, hire, and manage for you. Their approach aligns with what we know works—targeted, consistent support that integrates into your existing systems.
Instead of scrambling in the fall, you can put those supports in place now—so when the year begins, they’re already working. Connect with my friends at HeyTutor here.
The teachers who implemented project-based learning well all had one thing in common:
They asked for feedback.
They invited others in.
They sought guidance.
They refined their work along the way.
But we left that up to individual initiative.
And that was a mistake.
Because the people who need the most support are often the least likely to ask for it.
Support can’t be optional.
It has to be built into the system:
This may be the most important lesson of all.
If leaders don’t lead the work… the work doesn’t happen.
In our case, not every building leader fully embraced the initiative. Some said the right things, but didn’t follow through with consistent expectations or support.
And when that happens, the message to staff is clear—even if it’s unspoken.
This work is optional.
If I could go back, I would be much more intentional about:
Because alignment doesn’t happen accidentally.
It happens through leadership.
If you’re building a plan right now for next year, don’t just ask:
Ask:
Because those answers are what determine whether your plan succeeds—or quietly fades away.
We did some incredible things through that work.
Students had meaningful learning experiences.
Teachers created powerful opportunities.
But I still think about what could have been…
if we had everyone pulling on the same end of the rope.
The goal isn’t a perfect plan.
The goal is a plan that can survive reality.
Before you move on, take five minutes and ask yourself:
If those answers aren’t clear yet—that’s your next step.
And if you’d like support in getting there, I’m here to help.
