Engaging with Parents: From Conflict to Care

Fall 2024

By David Grant Smith

This article appeared as "From Conflict to Care" in the Fall 2024 issue of Independent School.

As a born pleaser, it has taken me many years to embrace disappointing people. But I now see its value. To disappoint is a kind of love. 

Educators can be especially conflict avoidant. We are the middle children of American industry. We like harmony and consensus. Blessed are we, the peacemakers.

But everyone who has ever stepped into an administrative role, driven by those core values, learns by the time they update their email signature that educational leadership is about negotiating conflict and navigating competing value sets. We love the idea of consensus, but sooner or later, we come to a stark realization: Often, our job is to disappoint. If we do this well, we learn to disappoint with love.

All of us who work in schools have an intuitive sense of care for our students. We understand that children aren’t supposed to get everything they want; saying no to our students doesn’t rattle us too much. But parent conflict? That’s why we have faculty happy hours. So often, we approach parent conversations on edge. We defend; we explain; we armor up. We feel like we need to win the argument. We prepare to play defense counsel and marshal evidence in support of our position. Or we ready for an attack and nimbly parry their concerns. 

But what if we reframe how we think about and engage our parents, even when we have to disappoint them and tell them what they don’t want to hear? What if we move from conflict to care?

Reframing the Parent Relationship

Like many in our vocation, for me, school leadership—and teaching more broadly—has always been a call to pastoral care. Channeling Simone Weil’s writing on education, I believe teaching is a call to love and listen to another soul with that deep attention that affirms their very being. School leaders must be deeply attuned to their communities, eager to meet individuals where they are in language that is meaningful to them. They must honor the dignity of the children under their care as well as the humanity and commitments of the families in their fold.

And yet, so often the daily realities of our roles seem to cut against the grain of our sense of our calling, to alienate us from the heart of care. As dean of students, it is often my job to tell people things they really don’t want to hear. It is often my job to deliver hard, occasionally terrible, news. It is my job to tell a family no, they cannot have a meeting with a teacher. It is my job to tell a family no, your child may not miss a day of classes for that special trip. It is my job to tell a family that their child will be suspended after a disciplinary case, and yes, it will appear on their records for college. And it has been my job, on more than a few occasions, to help tell a family that their child will be dismissed permanently from school. 

While repetition makes most hard things easier, these conversations have not become easier because I have hardened. Instead, I have reframed entirely how I think about them, how I think about conflict and disappointment. And as I approach them, I ask one simple question: What does care look like right now?

Earlier in my career, I always wanted to hedge. I wanted to soften. I wanted to find elusive third ways, via medias, between competing interests, values, and desires. To love seemed, in most cases, to accommodate and find common ground. But in June 2023, I was given new language. I was gifted new perspective that helped me think differently about my role and feel more aligned, feel a greater sense of integrity, when I couldn’t square all the circles. 

That summer I attended the Gardner Carney Leadership Institute (gcLi) Leadership Lab in Colorado. Of the many concepts we discussed, one shattered my ground: Leadership is disappointing people at a rate they can absorb. Drawn from Ronald Heifetz’s work on adaptive leadership, this idea resonated because I realized immediately that, on most days, this is the essence of my job. Or, as I often joke when people ask me what a dean of students does: My job is to disappoint everyone equally. 

Many of the tools we bring to difficult conversations with parents, like “collaborative problem-solving,” a powerful gcLi staple, aim to find mutually satisfying resolutions to conflict. Here, care is evident because preserving connection is at the heart of the practice. Parent conversations that demand unwelcome answers, however, can take on an inherent asymmetry that seems, necessarily, to sunder all connection. But after the Leadership Lab, I came to see disappointing as a process where we can nourish another human through a season of change or loss. I came to embrace the privilege of sharing these moments with a family. Conflict, disappointment, change—these are inevitable, and I get to walk alongside them. 

This reimagining allowed me to recognize that I didn’t have to live outside of myself, even in the most fraught encounters. I could preserve the pastoral charge. Difficult news didn’t mean emotional distance. Instead, I could convey a decision, listen deeply, stay connected to the feelings, and care.

Becoming Partners

These days, I think about this reframing mostly in my relationships with parents. While students are the heart of my daily work, increasingly parents play significant roles in how their children experience school. Parents shape a child’s own hopes, fears, and anxieties, and they craft a child’s own expectations for success. Now, a Jungian analyst will say this has been the case since the dawn of time. But, as we have all experienced, parents are increasingly adept at orchestrating how their children travel through their adolescent years. They are fervently committed to the scripts they have written for how this whole thing is supposed to play out. 

We don’t really know what to do with school parents, do we? In what other institution or organization is there an interest group with such a vital stake that is both deeply invested yet intentionally kept at bay? Churches, the closest institutions to schools, in my mind, don’t have this sort of appendage body politic. Even publicly held corporations, beholden to stockholders who have no day-to-day role in the company, readily acknowledge and respond to the power of those who own their capital. But school parents? We are grateful for their presence, but we really would prefer they stay out of the way. 

Perhaps our penchant for alliteration inclines us to talk about our parents as “partners.” Yet, do we really mean that? Surely not in the sense that we partner with just about anyone else in the school orbit. The good parent is the invisible parent—or the parent who is invisibly present. Seen but not heard. We like our parents to be available in support (dance chaperones, service drive coordinators, and carpool drivers). But we would prefer they remain silent on strategy or implementation of those aspects of school life most essential to our missions and institutional identities. 

The truth is, we ask parents to do this incredibly risky and brave thing: to hand over to us the care—and, at times, the parenting—of their children. We ask them to change in fundamental ways their roles and relationships to their children. We ask them, in short, to not be 21st century parents. Sometimes we ask this of that portion of parents most reluctant to do it.

To recognize our parents in this way is to acknowledge the very real and powerful feelings they carry with them when advocating for their children. It is to give them that precious attention that upholds their dignity and recognizes their hopes and fears. 

As I have come to consider the care embedded in disappointing, in holding lines and sharing hard news, I have come to think less about the “what” of the conflict and more about the way we hold the people before us, the way we connect to and carry their feelings in a painful moment. As the poet David Whyte says, there is a touch to delivering terrible news in a way that it can be heard fully; it must be said with the “intimacy of care and of understanding at the same time.” 

So that’s the job. Not to assuage, but to tell a parent hard news in a way that they know I love them and their child. In many of my conversations, I know I cannot tell a family a single thing they want to hear. I cannot give an inch. I cannot make anything better or change an outcome. But I know that a family can feel deeply cared for. And, in the end, they can feel grateful. They can know that, through it all, I am on their side.

What this also means in practice is releasing certain goals. In my conversations with parents, I no longer believe that success is achieving unity or consensus. I don’t hope they will be happy with the outcome. Instead, I keep my eye on a new horizon: What does care look like right now? 

Often, we may need to reset our expectations for what a contentious parent conversation might feel like. If our goal is not to agree or to get them to agree, not to argue or prove or convince but, with calmness and clarity, to tell them where we stand and care for them as they come to grips with a new reality, then we can take comfort in doing our job well. 

And, in the thick of it, we can always return to an essential question: What do you want most for your child? This is how we stay anchored in the mission. Usually, a parent’s answer to this question will reflect some aspect of our institutional mission. If not, a larger conversation may need to occur about our side of the covenant, about our promise to each child and family.

The Power in Disappointment

This is how disappointment is an act of love. Reframing disappointment as an act of love is not simply a way for me to excuse the act of being the bad guy, a mechanism for separating myself from the shared pain whenever I am the immediate cause of another’s heartache. My primary purpose is still to sit with the person in front of me and provide care. 

Another way to put this: More than anything, my job is to shepherd students and their parents through a difficult season of their life together. While the many obvious joys of school life sustain us in this calling, more often than not it is those less visible, even strained, moments of fracture, pain, reconciliation, and healing where the true beauty of this work comes to life. I have come to cherish those opportunities to care in hard times—even when, for a family in a crisis moment, I need to be the target of their anger. As any parent knows, being disliked can be a powerful form of love. 

Caring for parents is always about keeping the care of the child front and center, even when it can feel for them like the world is ending and there is no pathway forward. It is not about issuing false promises or false hopes. It is about a different kind of assurance: It’s going to be OK, even if OK doesn’t look like what anyone anticipated. 

Parents are not the enemy. And disappointing isn’t the end game or the end of the story. But sometimes it’s our job to help change the story or to help change how they think about the story. For their child, the hard thing can be the best thing, the most loving thing. Disappointing is where we start. Parents are every bit as anxious about the future as their children are. And they’re looking to us for a little hope, a little reassurance that this whole thing is going to work out. 

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David Grant Smith

David Grant Smith is dean of students at The Roxbury Latin School in Boston, Massachusetts.