If I’m honest, overextension has been one of my most consistent leadership mistakes.
As a principal, I took on too much because I cared deeply about my school, my staff, and my students. In my current work as a coach and speaker, I still sometimes catch myself saying yes when I should pause and ask a harder question about focus and capacity. In the moment, overextension feels responsible. It feels helpful. It feels like leadership.
But overextension rarely shows up as heroism. More often, it shows up quietly — through fatigue, rushed decisions, shortened patience, and a gradual erosion of presence.
Just this week, a leader shared a moment with me that stopped him in his tracks. During an exit interview, an employee mentioned that there were times the leader walked past them in the hallway without even acknowledging them. No greeting. No nod. No connection. The leader was genuinely surprised — and deeply bothered — by the feedback. He cared about his people. He valued relationships. This wasn’t who he believed himself to be as a leader.
But when we unpacked it together, the reason became painfully clear. He wasn’t disengaged. He wasn’t arrogant. He was overextended. His mind was already in the next meeting, the next issue, the next problem to solve. He was so stuck in the cycle of chaos that the interpersonal side of leadership had unintentionally slipped through the cracks.
That’s the danger of overextension. It doesn’t just affect productivity. It affects people.
Years ago, Howard Schultz came to a similar realization at Starbucks. During a period of rapid expansion, the organization was doing more than ever before. Stores were opening quickly, initiatives were stacking up, and leaders were stretched thin. On the surface, things looked successful. Underneath, focus was fading.
The Starbucks experience became diluted. Culture shifted. Innovation slowed. Schultz later acknowledged that in the rush to scale, the company had become overextended. Growth had outpaced clarity. Leadership attention had been spread too thin.
It wasn’t a lack of intelligence or passion that hurt the organization.
It was simply too much.
And leaders everywhere — in schools, districts, businesses, and organizations of every kind — are falling into the same trap.
The “O” in CHAOS
In the Cycle of C.H.A.O.S., the “O” stands for Overextension.
This is the stage where leaders keep adding without subtracting. Another initiative. Another meeting. Another responsibility. Another problem they decide to personally carry. All the while, they’re telling themselves that they just don’t have enough time to get it all done.
Overextension usually doesn’t come from ego. It comes from heart. Leaders care. They want to support their people. They want to make sure things are done well. So they take on more, often without realizing the cost.
Here’s the hard truth: when leaders carry too much, everyone else carries too little.
Over time, this creates dependency, reduces shared ownership, and keeps the leader trapped in reaction mode instead of leadership mode. Even more damaging, it begins to steal presence — the very thing people need most from their leaders.
Let’s Remove the Blame
Before going any further, this needs to be said clearly.
If you’re overextended right now, it does not mean you’re a bad leader. In most cases, it means you’re a deeply committed one who has been operating without enough margin for too long.
Most leaders I work with don’t struggle because they lack skill or care. They struggle because the system keeps pulling, the needs keep coming, and the calendar fills itself. Overextension isn’t a character flaw. It’s a pattern.
And patterns can be changed.
How to Begin Breaking the Overextension Cycle
This isn’t about fixing everything at once. It’s about creating space — mentally, emotionally, and structurally — so leadership can breathe again.
Start with awareness. For one week, take note of what you planned to do, what actually filled your time, and what consistently pulled you away from your priorities. Pay attention to which tasks truly required you, and which ones simply landed on your plate by default.
Next, slow down just enough to ask better questions. Before taking on or continuing a responsibility, ask yourself whether it needs to exist at all, whether it truly needs to be done by you, or whether it can be delegated with clear expectations. Overextension thrives when leaders move too fast to evaluate what they’re carrying.
Equally important is protecting time for leadership work — not just operational survival. Strategic thinking, culture-building, coaching conversations, and reflection don’t happen accidentally. If leadership presence matters, it must be scheduled and guarded.
Finally, remember that delegation is not abandonment. It is development. When leaders intentionally transfer ownership with clarity and support, they build confidence in others, increase organizational capacity, and reduce the unhealthy pressure of doing everything themselves.
The strongest leaders are not the busiest ones.
They are the most intentional.
Overextension and Leadership Presence
This is where everything connects.
Overextension doesn’t just exhaust leaders. It erodes presence. And presence is not about being everywhere. It’s about being fully somewhere.
When leaders are stretched too thin, conversations become rushed. Listening becomes shallow. Relationships begin to feel transactional rather than human. Culture shifts from something that is intentionally cultivated to something that is merely maintained.
In the three-part podcast series I recently released on leadership presence, I talk about this directly. Presence is the multiplier. When leaders show up with clarity and focus, their leadership carries weight. When they don’t, even the best intentions fall flat.
You cannot be fully present when you are perpetually overextended.
And people feel that — even when leaders don’t intend it.
Breaking the Cycle
If you see yourself in this — if your days feel full but unfulfilling, if your calendar is packed but your leadership feels thin — please hear this with compassion.
You are not failing.
You are likely stuck in a cycle.
And cycles can be broken.
The work I do with leaders centers on helping them step out of the Cycle of C.H.A.O.S., regain clarity, and lead with intention instead of reaction. This isn’t about doing more. It’s about doing what matters most, with focus and presence.
Because leadership isn’t measured by how much you carry.
It’s measured by how well you show up.
And presence begins when overextension ends.
If you’re a regular listener of the Leaning Into Leadership podcast, you’ve probably already heard me talk about my friends at HeyTutor.
HeyTutor delivers customized, evidence-based, high-dosage math and ELA tutoring for K–12 school districts across the country, offering both in-person and online options. Their programs are aligned to state standards and designed around real, measurable results—including one of the few tutoring models that has been vetted and awarded Stanford’s National Student Support Accelerator badge.
What really sets HeyTutor apart is that they handle the heavy lift. They recruit, train, hire, and manage tutors as HeyTutor employees, so districts don’t have to scramble to find staffing or manage another system. Their curriculum and platform tools also make it easy for schools to track student growth through an accessible dashboard for tutors and teachers.
If your district is looking for tutoring support that’s structured, scalable, and built for impact, HeyTutor is worth a look. You can learn more about their work at heytutor.com.
Make sure to tune in this week to the Leaning into Leadership podcast where I’ll continue with the second part in my three part series on leadership presence.
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