Later this week I’ll be speaking to a room full of school leaders about a topic that doesn’t get nearly enough attention: leadership teams.
Most organizations have one. Every school certainly does. Principals have assistant principals, instructional coaches, counselors, department chairs, and other key leaders who help move the work forward.
But having a leadership team and functioning as a leadership team are not the same thing.
Over the years, I’ve asked leaders in many different settings two simple questions.
What makes a leadership team exceptional?
And then…
What causes leadership teams to struggle?
The answers to the first question usually come quickly. Leaders talk about trust, communication, shared goals, and accountability. They describe teams where people support one another, challenge each other respectfully, and move the organization forward together.
But when we shift to the second question—why teams struggle—the conversation becomes much more interesting.
Leaders talk about unclear roles. Competing priorities. Meetings that feel productive but never seem to lead anywhere. Avoiding difficult conversations. Leaders working incredibly hard but somehow still feeling out of sync.
And as I listen to these conversations, a pattern always emerges.
Most leadership teams aren’t struggling because the people on the team don’t care.
They’re struggling because the team itself was never intentionally designed.
One of the frameworks I’ve been sharing with leaders recently is what I call the Cycle of CHAOS. It describes the environment many leaders find themselves operating within:
Constant Reactivity
The day becomes a series of responses to problems instead of intentional leadership.
High Cognitive Load
Too many initiatives, too many decisions, too many competing priorities.
Absence of Clarity
Unclear expectations, unclear roles, and shifting priorities.
Overextension
Leaders trying to do too much, often stepping into work that should belong to someone else.
Survival Mode
Moving from one challenge to the next with very little time to step back and think strategically.
When leaders find themselves stuck in this cycle, the leadership team rarely becomes stronger. Meetings become reactive. Conversations become corrective. Instead of operating as a unified team, leaders begin operating as individuals trying to manage their own corner of the organization.
No one intends for it to happen this way. It simply becomes the default.
If leadership teams want to operate at a higher level, they have to pause long enough to ask some important questions.
Does every member of our leadership team clearly understand their role and decision authority?
Are the decisions we make aligned with a shared vision for where our organization is headed?
Do our leadership team meetings focus primarily on strategic priorities, or do they revolve around reacting to the latest problem?
Can members of the team raise difficult issues openly, or do certain conversations remain unspoken?
Do we spend intentional time working on our organization, or are we constantly buried in the work within it?
These questions are not always comfortable, but they are essential. Leadership teams that never ask them often find themselves drifting further into chaos without realizing it.
The strongest leadership teams I’ve been part of—and the ones I’ve had the privilege of working with—tend to share several characteristics.
First, they have clarity of roles. Each leader understands their responsibilities, where their authority begins and ends, and how their work complements the work of others. This clarity allows the team to move forward without duplicating effort or stepping on each other’s toes.
Second, they operate around a shared vision and mission that the team has helped create. This vision isn’t simply a statement posted on a website. It becomes a filter for decision-making, helping the team stay aligned even when challenges arise.
Third, exceptional teams develop a willingness to cross-train without doing each other’s work. Leaders understand the responsibilities of their teammates and can support one another when needed, but they also respect the distinct roles each person plays.
Finally—and perhaps most importantly—these teams create intentional time to step back and strengthen how they work together. They don’t assume alignment will magically appear in the middle of a busy school year or a packed meeting agenda.
They build it.
Exceptional leadership teams don’t happen by accident. They are the result of clarity, alignment, and intentional leadership.
That work might happen through honest conversations about roles and expectations. It might involve revisiting the team’s shared vision and priorities. Often, it requires stepping away from the daily demands long enough to focus on how the team itself functions.
But the work is worth it.
Because when leadership teams operate with clarity and alignment, the entire organization benefits. Communication improves. Decisions become more consistent. Leaders support one another rather than working in parallel lanes.
And perhaps most importantly, the team moves from reacting to challenges toward intentionally leading the organization forward.
Before your next leadership team meeting, it may be worth asking one simple question:
If our leadership team continued operating exactly as it does today, where would our organization be two years from now?
The answer to that question may reveal the next conversation your team needs to have.
And the next mile you need to build together on the Road to Awesome.
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.
