This week in Orlando, I had the opportunity to work with school leaders on a challenge that almost every organization faces but few address intentionally:
Leadership team alignment.
Most leadership teams don’t struggle because people aren’t trying hard or lack skills. They struggle because everyone is busy. Everyone is carrying responsibility. Everyone is trying to solve problems quickly. And when that happens, something subtle begins to occur.
The team drifts out of alignment.
Different priorities emerge. Communication becomes reactive. Decisions start getting made in silos. Before long, the team that is supposed to lead together begins operating more like a group of individuals working in parallel.
That’s why I’m a strong believer in intentional leadership retreats, especially during the summer when the pace allows leaders to step back and think strategically. A well-designed retreat isn’t about team-building games or escaping the office for a day.
It’s about alignment.
Years ago, when I was serving as a high school principal, our leadership retreat became one of the most important investments we made each year. It was where we reset expectations, clarified priorities, and made sure everyone was pulling in the same direction before the school year began.
Looking back, the structure of that work fits almost perfectly into the ALIGN framework I now use with leadership teams.
The first question every leadership team must answer is simple but powerful:
What are we truly trying to accomplish this year?
Too often teams operate with vague ideas about improvement without naming the few priorities that actually matter most.
During our retreats, we spent time identifying:
• The 2–3 outcomes that would define a successful year
• The cultural priorities we wanted staff and students to feel
• The instructional focus we wanted to see in classrooms
When a leadership team becomes clear on these priorities, decision-making becomes much easier.
Without that Clarity, everything feels urgent.
One of the most common leadership frustrations I hear from principals and district leaders is this:
“I thought we were on the same page.”
The reality is that communication inside leadership teams is often assumed rather than designed.
Retreats give teams the space to ask important questions like:
• How will we communicate decisions to staff?
• When do we meet as a leadership team?
• How do we handle disagreement?
• What information must be shared before decisions are made?
When communication systems are intentional, confusion disappears quickly.
Misalignment often happens when leadership teams have overlapping responsibilities or unclear ownership.
In our retreats, we spent time clarifying:
• Who owns each priority area
• Where collaboration is required
• Where autonomy is expected
This step is incredibly powerful because it reduces friction.
When leaders know where they lead and where they support others, the team becomes far more effective.
Alignment cannot exist without trust.
And trust does not happen automatically just because people sit at the same leadership table.
Retreats allow teams to:
• Reflect on past challenges
• Address lingering frustrations
• Build stronger Relationships
Some of the most important moments from our retreats didn’t come from formal agenda items.
They came from conversations during meals, walks, and informal reflection time.
Those moments helped our team learn how to lean into each other rather than work around each other.
Finally, the retreat must end with a clear plan.
Alignment means very little if it doesn’t translate into action.
Before leaving our retreat, we made sure we had clarity around:
• Our leadership team meeting schedule
• How we would monitor progress toward our priorities
• What success would look like at the end of the year
Those conversations created accountability—not in a punitive way, but in a way that kept us focused on what mattered most.
Summer retreats work because they happen before the chaos of the school year begins.
Once the year starts, leaders are pulled into a hundred directions.
Meetings multiply.
Emails pile up.
Unexpected challenges appear.
Without intentional alignment beforehand, teams quickly move into reaction mode.
A summer retreat creates the space to step onto the balcony, see the bigger picture, and start the year with shared clarity.
When leadership teams are aligned, schools feel different.
Decisions become clearer.
Staff trust leadership more.
Students experience greater consistency.
Alignment doesn’t happen by accident.
It happens when leaders take the time to step away from the daily work and focus on how the team will lead together.
And sometimes, the most important work a leadership team can do is simply this:
Step away, think together, and realign before the year begins.
Strong leadership teams spend their time focusing on the work that matters most—supporting teachers, strengthening culture, and improving outcomes for students.
But that kind of focus is difficult when leaders are constantly trying to solve operational challenges that could be better handled by trusted partners.
That’s why I appreciate the work being done by my friends at HeyTutor, a sponsor of this blog and the Leaning Into Leadership podcast.
HeyTutor delivers customized, evidence-based math and ELA tutoring programs for K–12 districts nationwide. Their tutoring model is aligned to state standards and designed to produce measurable student Growth. In fact, it’s one of the few tutoring models to earn Stanford’s National Student Support Accelerator badge.
Even more importantly, HeyTutor manages the entire tutoring process—from recruiting and training tutors to managing staffing and scheduling. Their platform also allows teachers and administrators to easily track student progress through a simple dashboard.
If your district is exploring ways to expand student support while allowing your leadership team to stay focused on strategic priorities, you can learn more about HeyTutor at heytutor.com.
