The Courage to Lead When People, Money, and Morale Are All at Stake

 

Montessori school leadership is often discussed in terms of vision, values, and philosophy. But day-to-day reality unfolds in far more complicated terrain—at the intersection of people, money, morale, and mission, where every decision feels consequential and often personal.

Today’s Montessori leaders navigate an especially fragile landscape. Teachers are challenging to find, and support staff are stretched thin. Burnout is real, and the fear that a valued teacher might leave—seeking higher pay, less stress, or relief from constant pressure—can lead to difficult decisions. Leaders must balance staff retention efforts with maintaining high standards to ensure school stability and quality.

Courageous leadership doesn’t ignore these realities. But it also doesn’t allow fear to dictate the school’s future quietly. Instead, it works through influence, systems, and sustained attention to the people who make the school work.

Montessori as a System of Systems

Montessori education itself can be understood as a system of systems—ways of organizing time, space, materials, curriculum, and human relationships that work together to support children’s development. While there can be legitimate disagreement about how to implement or organize these systems, schools work best when there is a common understanding about how we do things here.

This doesn’t mean imposing rigid uniformity or stifling professional judgment. It means developing carefully crafted agreements about the fundamentals:

• How we treat each other—children, families, and colleagues
• How we organize the day and the program at each age level
• What Montessori and supplementary materials are needed for each classroom
• What standards of cleanliness, order, and timeless beauty we maintain in our indoor and outdoor environments
• What curriculum do we expect all children to experience, beyond their individual interests
• What children should know or be able to do before progressing to the next level
• How we respond to children who are struggling
• How we work with challenging parents

When these agreements are clear, stress and resentment decrease. People know what’s expected. They can focus on their work rather than navigating constant uncertainty or dealing with conflicting work.

The key is that these agreements shouldn’t simply be imposed by leadership. They need to be developed thoughtfully, with input from those who will live by them, and then memorialized in writing as part of an organizational blueprint—a master plan or manual of how things work at our school. This living document serves as a reference point for everyone and a crucial tool for onboarding new community members.

The school can’t reinvent itself every time someone new joins. But neither can it ignore the need to help newcomers understand and embrace these shared agreements.

Courage in a Time of Scarcity

Staffing scarcity defines modern Montessori leadership. Experienced teachers are in short supply. Assistants and support staff are harder than ever to recruit and retain. Leaders know that replacing a teacher isn’t a simple transaction—it can take months, sometimes years. The disruption to children, families, and morale can be profound.

As a result, many leaders hesitate to:

• Address misalignment or underperformance
• Introduce needed changes in practice or structure
• Make decisions that might be unpopular in the short term

The tendency to hesitate is understandable, but when fear of losing staff becomes the primary driver of decisions, the hidden costs accumulate. Standards erode. Resentment builds quietly among other staff. Strong teachers carry the emotional and practical load for those who are disengaged. Over time, morale suffers anyway.

Courageous leadership doesn’t mean ignoring scarcity. It means leading through it, rather than around it—by building systems and relationships that help people grow, feel supported, and work effectively together. And it means being thoughtful about who joins the community in the first place.

Taking Time to Find the Right Fit

One of the most important ways leaders protect their schools is by resisting the pressure to rush. When there’s an opening—whether for a teacher, assistant, specialist, or administrator—the temptation to fill it quickly can be overwhelming. When enrollment is soft, the pressure to accept any family willing to pay tuition is intense.

But courageous leadership means taking time in both hiring and admissions to find people who will be happy at the school and become great members of the community.

Before making an offer of employment or admission, both parties need time to get to know each other. Prospective families need to understand what they’re agreeing to—not just the philosophy in the abstract, but the practical realities of how the school operates. Prospective staff members need to understand not only their role, but the social norms and expectations of the community they’re joining.

Not every family will care deeply about understanding Montessori education—some are just trying to solve a childcare problem. But they still need a certain level of understanding right from the start. It’s far easier to establish shared expectations at the beginning than to try to change someone once they’re already part of the school.

The same is true for staff. Taking time to find the right fit can build confidence that the school is making thoughtful decisions, leading to greater stability and coherence.

Leading Through Influence, Not Just Authority

Decades ago, Peter Drucker highlighted how managers make things happen through influence, which can inspire Montessori leaders to foster trust and responsibility rather than relying solely on authority. 

Time and presence matter. Leaders who regularly spend time in classrooms signal that they care about what’s happening and who’s doing the work. Teachers notice when leaders show up—not to evaluate, but to understand, support, and stay connected to the daily reality of the classroom.

Coaching and support build capacity. Providing teachers with thoughtful, ongoing coaching—not just annual observations—helps them develop their practice and feel genuinely supported. This is especially important for support staff and specialists who may not have Montessori training. Rather than leaving them to feel inadequate or guilty about what they don’t know, leaders can create pathways for learning and growth.

Systems create space for collaboration. Organizing regular meeting time, planning structured opportunities for reflection and team-building, and creating traditions that bring people together all help build the connective tissue of a healthy school. Beginning-of-year team building and end-of-year reflection aren’t luxuries—they’re how shared understanding develops and how those foundational agreements get refined and renewed.

Communication shapes culture. Leaders influence their schools by how they communicate with all stakeholders—teachers, assistants, parents, students, boards, and partners. Effective communication doesn’t overwhelm people with information, nor does it leave them guessing. It’s clear about expectations, transparent about challenges, and consistent in tone and frequency.

Onboarding sets the foundation. Careful onboarding of new staff and families establishes expectations, builds relationships, and helps people understand not only their roles but also how their work connects to the school’s larger purpose and the carefully developed agreements about how we do things here. Poor onboarding leaves people adrift; thoughtful onboarding creates belonging.

These aren’t add-ons to leadership. They’re how leadership actually happens—through sustained attention to people, structures, and relationships.

Making Everyone Feel Seen, Heard, and Valued

One of the most important goals of Montessori leadership is ensuring that every member of the community. feels seen, heard, and valued. 

Parents may feel they’re not good enough or not part of the crowd because of race, religion, gender, wealth, level of education, or some other factor. Leaders must actively work to counteract this through how they communicate, how they welcome families, and how they create opportunities for connection that honor different circumstances and comfort levels.

Not every parent has the same time availability or interest. Some will eagerly engage with every aspect of school life; others are simply trying to solve a problem and get through the day. The goal isn’t to force everyone into the same mold, but to ensure everyone has access to the information and support they need, and that no one feels excluded or diminished.

The same principle applies to staff. Everyone—from the newest assistant to the art teacher, from office staff to administrators, from veteran guides to brand-new teachers—needs to feel that they matter. Support staff and specialists, who often feel invisible because they’re not Montessori-trained classroom teachers, especially need deliberate inclusion in the school’s mission and community.

Helping everyone feel that they are part of the fabric of the school requires ongoing effort. It’s not something you do once during onboarding and then forget. It means continually creating opportunities for connection, recognition, and meaningful participation. It means paying attention to who speaks and who doesn’t, who feels comfortable and who seems hesitant, who gets recognized and who gets overlooked.

Working With Resistance When the Stakes Feel High

Resistance to change intensifies when leaders feel they cannot afford to lose people. A teacher who says, “I’ve been doing this for thirty years,” or “This is not how I was trained,” may feel untouchable—not because their practice is beyond question, but because the leader fears the consequences of conflict.

Here, courage takes a relational form. It asks leaders to engage resistance thoughtfully rather than avoid it. To separate respect for experience from unquestioned authority. To create space for dialogue while maintaining clarity about expectations.

This is where influence-based leadership and those shared agreements become essential. Rather than issuing mandates, effective leaders:

• Name shared goals for children, framing change around student needs rather than teacher shortcomings
• Return to those foundational agreements about how we do things here—not as weapons, but as touchstones for dialogue
• Create structured time for faculty to explore new ideas together, building consensus rather than imposing change
• Provide professional development and coaching that helps teachers see possibilities rather than threats
• Help people become more reflective and supportive of each other through facilitated conversation
• Are transparent about what is essential to the mission and what is open to discussion
• Accept that not everyone will choose to stay—and that this, while painful, is sometimes part of organizational health

Montessori schools don’t thrive because everyone agrees. They thrive when leaders create the conditions for honest dialogue, mutual support, and shared commitment to children.

Morale, Stress, and the Adult Prepared Environment

Teacher morale isn’t only a function of workload or compensation, though both matter deeply. It’s also shaped by clarity, consistency, and trust. In schools where expectations are ambiguous, decisions feel arbitrary, or leaders appear hesitant, stress increases—even when leaders believe they’re being protective.

Carefully crafted agreements about ‘how we do things’ are very helpful. When people understand the systems and trust that they will be implemented consistently, they can relax into their work. When standards shift depending on who’s asking or what day it is, everyone operates in a state of low-grade anxiety.

Adults, like children, need a prepared environment. They need:

• Clear roles and boundaries
• Predictable systems and rhythms
• Honest, regular communication
• Leadership that is calm, present, and consistent
• Time and space for collaboration and community-building
• Recognition that their work matters
• Shared understanding of how things work here

Support staff and specialists—who often feel invisible because they’re not Montessori teachers—especially need to feel included in the school’s mission and supported in their work with children. When leaders create systems that honor all adults in the building, morale strengthens across the entire community.

Ironically, when leaders avoid difficult conversations out of fear of harming morale, morale often declines anyway. Staff sense uncertainty. Strong teachers feel unsupported. The emotional load shifts sideways rather than disappearing.

Courageous leadership recognizes that structure is a form of care—and that investing time in people’s growth and connection is not a luxury but a necessity.

Financial Courage in a Fragile Staffing Market

The fear of losing teachers also shapes financial decisions. Leaders know compensation matters, but they also know tuition has limits. Parents may resist increases. Markets vary. Not every school can simply “charge more.”

This is where courage becomes strategic and creative rather than simplistic—and where communication becomes critical.

When a school is underfunded, leaders must explore multiple avenues simultaneously:

• Reduce expenses thoughtfully without cutting quality
• Strengthen marketing and admissions to fill empty spaces—but without rushing or compromising on fit
• Help families understand the value of Montessori education more clearly through consistent, honest communication
• Use financial aid strategically to support access while protecting sustainability
• Align staffing models with enrollment realities rather than historical patterns
• Work with parents so they feel honored and understand both what the school asks of them and what the school is committed to providing.

Financial courage isn’t about pretending constraints don’t exist. It’s about refusing to accept chronic scarcity as inevitable—and being willing to have honest, ongoing conversations with all stakeholders about sustainability.

Leading With Others, Not Alone

For many Montessori leaders, these decisions are complicated by governance structures—boards, owners, or partners who may not fully understand Montessori education or the daily realities of staffing and morale.

Again, courage isn’t confrontation for its own sake. It’s persistence, education, and conversation. Building consensus over time and staying engaged even when progress is slow.

This requires the same influence-based approach that works with faculty:

• Regular, structured communication that keeps boards and partners informed without overwhelming them
• Helping them see the whole picture: how financial instability affects staff well-being, how unclear expectations undermine morale, how avoiding change today often creates greater disruption tomorrow
• Creating opportunities for board members or partners to experience the school directly—to see classrooms, meet teachers, and understand the work.
• Building shared language and understanding about what makes Montessori education work.
• Developing those foundational agreements together, so that governance partners understand and support the school’s organizational blueprint

It means resisting the temptation to disengage when alignment feels difficult, and instead finding ways to bring people along.

Leadership as Steady Presence

At its heart, Montessori leadership isn’t about eliminating anxiety—your own or others’. It’s about becoming a steady presence within it.

Leaders can’t promise teachers that nothing will change or that stress will disappear. What they can offer is honesty, clarity, and a commitment to building a school worthy of people’s energy and talent.

School leaders support this through:

• Showing up consistently in classrooms
• Creating and maintaining systems that support collaboration and growth
• Developing and stewarding those foundational agreements about how we do things here
• Communicating clearly and regularly with all stakeholders
• Investing in people’s development through coaching and professional learning
• Taking time to find the right fit when hiring or enrolling new members
• Building community intentionally, not accidentally
• Making space for reflection, celebration, and honest assessment
• Ensuring everyone—parents and staff alike—feels seen, heard, and valued

Yes, leadership can feel like herding cats. But it’s also the work of pathfinding—helping an organization move, step by step, toward sustainability, coherence, and trust.

When Montessori leaders lead with courage in this fuller sense—acknowledging scarcity, caring for morale, building systems that support people, trying to confirm that prospective employees and families will be a good fit, creating shared agreements about how things work, and still making principled decisions—they create schools where great teachers are more likely to stay, not less.

Not because leadership avoided difficulty, but because it faced it with integrity—and built the structures, relationships, and shared understandings that help everyone do their best work.