Boundaries Create Culture

Of Crop Dusters and Tree Lines

I once saw a single conversation transform a school’s culture.

At the time, I was a junior administrator responsible for disciplinary processes. After one serious incident resulted in a consequence, the student’s father—who also happened to be a board member—decided to come after me. He went to my supervisor, then the head of school, accusing me of lying and fabricating evidence.

It was frustrating. And insulting. And more than a little scary.

I was just a month or so from completing my contract and moving away. The leadership team must have been tempted–even if just a little– to placate and support this powerful board member rather than standing up for an unimportant junior administrator about to leave. But that’s not what they did.

Instead, they said the following: “When we blame hard-working administrators for disciplinary situations, we prevent our children from learning from their mistakes.”

I’ll never forget how it made me feel to hear about this conversation.

I felt so honored and taken care of. They had the courage to speak the truth and hold the line. The harmful behavior wasn’t allowed to stand, even when the one exhibiting the behavior was powerful and important.¹ And because of conversations like this one, the employees at our school knew that we could rely on the leadership team, and the school culture flourished.

These are the conversations that make or break educators’ sense of belonging.

Regenerative Farmers Block Toxic Chemicals

I’m reminded of a story my dad told me about boundaries in regenerative farming. His little farm is surrounded on all sides by conventional, chemical-based farms. While his regenerative farm is organic, all the neighbors spray pesticides.

Unfortunately, the neighbors’ pilots flying crop dusters are not always as precise as they should be. More than once, a crop duster missed the edge of a neighbor’s field, spraying pesticides directly onto the regenerative farm. When that happened, the effects were deeply harmful: the crops could no longer be classified as organic, so they lost much of their value. The pollinators were wiped out. The carefully tended soil was polluted.

Fortunately, one of my father’s colleagues had a great solution to this decades ago. They planted a double tree line all along the boundaries to the regenerative farm. The trees formed an unmistakable boundary line, and once they grew tall, they literally forced the crop dusters to pull up their planes and turn around so as not to run into that barrier.

The trees aren’t out picking a fight with the chemicals. But there they stand. Unapologetically setting a barrier, preventing toxins from polluting the farm.

I see the role of regenerative leaders much like that tree line. We set the boundaries of what we allow into our community by which behaviors we address and which we let slide.

When we’re at our best, we prevent the toxins of harmful behavior from polluting our community and tanking our culture.

Ripple Effects

Having hard conversations, holding others accountable, speaking the truth with respect and dignity – these might be the hardest parts of leadership. But it’s so worth it. Because not holding boundaries ripples out with disastrous effects.

In his memorably named book The No Asshole Rule, Robert Sutton puts it this way:

The bad news is that these oppressors cost organizations far more than their leaders usually realize. The good news is that if you devote yourself and your organization to establishing and enforcing the no asshole rule, you can save a lot of money and save your people, their friends and families, and yourself a lot of heartache.

It’s so easy to underestimate the damage of allowing toxic behaviors to slide.

Thinking back to the story at the beginning of this essay, what would have happened if the leadership team had not set a clear boundary with the board member who accused me of framing his son?

First, I would have been crushed— I would have felt totally undermined, and that I couldn’t effectively do my job of managing our restorative processes. The next time a disciplinary situation came up, I would have spent my energy in self-protective mode, unable to effectively give consequences to students, knowing that if their parents went above my head that I could be undermined again. The floor would have dropped out of my sense of belonging, propelling me toward absenteeism and burnout.

Second, the teachers who witnessed the bullying situation by the son and then saw that the father could himself bully his way to a favorable outcome would also have felt their sense of emotional safety drop. As the story got out, teachers would be less likely to bring forward similar situations, knowing that the boundary wouldn’t be set. Eventually, this culture of cynicism would even impact teacher retention. No one wants to work for a boss who doesn’t have their back.

Third, the students who saw the original bullying situation would see that the powerful board member’s son got away with it. They would pass around that key takeaway: we can’t trust adults. A culture of fear would have proliferated among students, as the more powerful students could act with impunity towards those with less power.

The ripples just keep moving outward.

A single crucial boundary-setting conversation has massive effects on school culture as a whole, both students and adults. How do I know? Because I’ve worked in schools where the leaders were unwilling to have these hard conversations. I’ve felt myself retreat into self-protective mode, knowing that my boss didn’t have my back. I’ve seen the culture of care disintegrate into a culture of fear, impacting teacher and even student retention. It’s exhausting to work in a school like that.

None of us enjoy hard conversations. But this experience taught me just how crucial it is for leaders to have the courage to engage in them.

Mindset Shifts for Regenerative Leaders

In next week’s essay, I’ll explore concrete steps to set healthy boundaries in your school, protecting your community, living your values, while also sustaining your own emotional health.

But new systems and strategies will never stick unless we commit to regenerative mindsets to underpin them. So as a school leader, start by asking yourself:

What is a hard conversation that I’ve been avoiding?

What might be stopping me from holding a boundary that I believe in?

What would help me summon up the courage to be direct and clear?

Because just like regenerative farmers don’t allow pesticides to pollute their farm, regenerative leaders don’t allow toxic behaviors to permeate our schools. When leaders find their courage to set healthy boundaries, then everyone thrives.

Citations:

Abrams, Jennifer. Having Hard Conversations. Corwin, 2009.

Hain, Raymond. Personal Interview. November 2025.

Sutton, Robert. The No Asshole Rule: Building a Civilized Workplace and Surviving One that Isn’t. Balance Publishers, 2010.

1. Note that this happened within a context of a school deeply shaped by SEL and restorative practices. I also believe that boundaries can be harmful when overly punitive, but my experience in schools has been that leaders that are too lax are just as harmful. I particularly resonate with Jennifer Gonzalez’ analysis of this in her blog post “Where Discipline Reform Has Gone Wrong.”

Ruth created the image at the beginning of this post using Canva AI image generator.