The Middle Is Where the Real Work Happens
If you’re a department chair, dean of students, director of studies, or division director, you already know the feeling. You’re responsible for outcomes you don’t fully control, accountable to leaders above you while advocating for the team below you, and somehow expected to make institutional initiatives land gracefully on a Tuesday afternoon. It is complex, often thankless, and absolutely critical to how a school functions.
In a recent episode of The Table, I had the pleasure of speaking with Meredith Herrera, a nationally sought-after certified executive coach with nearly 20 years of senior leadership experience. Her work focuses specifically on supporting leaders in complex organizations, including those in the middle of the school org chart. What emerged from our conversation was a rich, practical roadmap for anyone navigating this uniquely demanding layer of school leadership.
Meredith’s framing was direct: “Middle managers are the connective tissue of an organization.” They translate vision into action, absorb pressure from multiple directions, and do it all while remaining the emotional center of their teams. That’s not a small ask.
Why Leading From the Middle Feels Different
Leadership, as Meredith reminded me, is not about title. It’s about behavior, presence, and the consistent micro-moves that shape culture every day. But what makes the middle uniquely challenging is the structural tension baked into the role itself.
Middle leaders often carry a high degree of responsibility without equivalent authority. A department chair, for example, may be tasked with implementing a school-wide curricular initiative while having no formal power to compel participation from colleagues. A dean of students redesigning the advisory program has to coordinate with the division director, the athletic director, the communications team, and possibly others, before anything can move forward. As Meredith put it, that level of coordination requires someone who is “incredibly flexible, agile, willing to pivot, and able to do all of that while remaining emotionally constant.”
She also raised something that doesn’t get enough airtime: the problem of unseen work. Middle leaders are often the last to be recognized and the first to be blamed when something goes sideways. That lack of visibility is one of the structural features of the role that makes it particularly draining over time.
Navigating Up: Making It an Easy Yes
One of the most actionable frameworks Meredith shared was around what she calls “managing up” effectively. The goal isn’t to present a perfect plan. It’s to present a sound process.
When advocating for an initiative or bringing a proposal to senior leadership, strong middle managers anticipate resistance across all constituencies: students, parents, faculty, and staff. They show up with a plan for that resistance already mapped out. According to Meredith, “When you come to me with solutions and you’ve anticipated resistance in each demographic of the school, I may not know if this initiative will be successful, but I’m thinking: they’ve got it.”
She was also clear about what undermines this process, something she calls “anticipation defeat.” This happens when a leader unconsciously leads with every reason an idea won’t work before the idea has even been tested. Naming constraints is important, but leading with failure projections signals a lack of confidence and makes it harder for those above you to say yes.
The alternative is building what Meredith describes as “an architecture of implementation,” a phased approach with built-in checkpoints that allows leaders to beta-test initiatives, gather data, and adjust in real time. Presenting a robust process, not a polished product, is what earns trust at the senior level.
Navigating Down: Trusted Over Liked
Meredith was equally thoughtful about the dynamics of leading a team. She referenced advice from her own early mentor: there is a meaningful difference between a leader who is liked and a leader who is trusted. The goal is the second one.
What builds that trust? Consistency, transparency, and the willingness to deliver difficult news without hedging. Meredith was direct about a pattern she sees regularly: leaders who say one thing in a department meeting, then quietly abandon that position outside of it. That kind of inconsistency erodes trust faster than almost anything else.
She also pushed back on the idea that being a good middle manager means being a relentless advocate for everything your team wants. “One of the mistakes I see some middle managers make is that they perceive themselves as a union rep,” she noted. In reality, middle leaders hold context their team members often don’t have access to. Part of the role is helping people understand decisions within that broader context, not simply championing every concern upward regardless of fit.
Practically speaking, Meredith also offered some tactical guidance that is genuinely underutilized in schools: structured one-on-one meetings with everyone you supervise, team agendas shared in advance, and a consistent cadence of feedback that flows both directions. “You need to build capacity, not dependency,” she said. Those regular check-ins are where that distinction is made real.
Navigating Across: Influence Over Authority
Some of the most useful insight Meredith shared was around lateral leadership, working with colleagues at the same level in the organization. Research on organizational dysfunction, she noted, suggests that most institutional failures happen not at the top or the bottom of the org chart, but at the handoffs between departments and roles.
This is where relationship-building becomes a genuine professional skill, not a soft add-on. As Meredith put it, “Your presence sets the tone long before your position.” When you need to coordinate across campus, the quality of those relationships determines whether you get what you need and when.
She was also pointed about ego. Cross-functional collaboration breaks down when leaders lead with their credentials or their certainty. Getting things done across peer relationships requires “getting your ego out of the way,” a discipline she coaches actively. What facilitates collaboration, she often asks leaders, is the same set of ingredients that makes any successful partnership work: reliability, clarity about roles, honest communication, and enough goodwill to weather moments of friction.
For leaders who oversee work that touches many departments, especially in student life, Meredith’s guidance around clear scope and timeline is particularly relevant. If the people you need help from don’t know exactly what’s being asked of them and by when, you’ve already introduced confusion that will cost you.
The Extra Weight Carried by Marginalized Leaders
Meredith was candid about something that many institutions still underaddress. The bar for middle leadership is not the same for everyone. Women, BIPOC leaders, and neurodivergent leaders often face different scrutiny, double-bind expectations, and an invisible labor tax that comes from having to navigate organizational culture on multiple levels simultaneously.
She noted that many historically marginalized leaders have been socialized to over-function as a way to build credibility, taking on invisible labor that accumulates over time and contributes to burnout at higher rates. This is not a personal failing. It is a structural reality that thoughtful schools need to actively address.
At the same time, Meredith pointed to the unique strengths that many of these leaders bring: a heightened sensitivity to cultural shifts, the ability to synthesize diverse perspectives, and a well-developed capacity to hold complexity. These are assets. Schools benefit when they are recognized and leveraged, not simply demanded without support.
When You Feel Stuck: A Practical Reset
For leaders who feel like their influence has dried up, Meredith offered a grounding exercise she calls “power mapping.” The questions are simple but clarifying: Who already trusts me? Where does my input shape decisions, even indirectly? When things get complicated, who seeks me out? And where am I spending energy with very little return?
Alongside that, she recommends returning regularly to three centering questions: What can I decide? What can I influence? And what do I need to stop owning? Middle managers, she observed, frequently carry responsibility for things outside their control. Shifting from “how do I control this outcome?” to “how do I maximize my influence here?” is a mindset change that changes everything about how the role feels.
She also offered something practical that sounds almost too simple: stop overworking. “If you’re eating lunch while proctoring and checking email,” she said, “that’s not sustainable.” The leaders who model boundaries are the ones whose teams actually believe it when they’re told to rest.
What Schools Owe Their Middle Leaders
The conversation with Meredith left me thinking about institutional responsibility. If middle leaders are, as she says, “your frontline soldiers” and the band of leadership that gets the least support, then schools have work to do.
That means providing clear scope of authority alongside responsibility. It means building structures where middle leaders have protected time for one-on-ones, team meetings, and their own professional development. It means recognizing their work publicly and consistently, not just when something goes wrong.
And it means understanding that the health of your adult population and the health of your student population are in a bilateral relationship. When middle leaders are supported, they lead with more steadiness, more creativity, and more care. That filters directly into classroom experience, school culture, and ultimately, the outcomes that matter most.
If you’d like to connect with Meredith Herrera or learn more about her coaching work with school leaders, visit mherreraconsulting.com or find her on LinkedIn. She offers individual leadership coaching, group coaching for department chairs and deans, and team strategy work for schools navigating change.
You can listen to the full episode of The Table wherever you get your podcasts. If this conversation resonated with you, share it with a colleague who is doing the hard work of leading from the middle.
