You're Not Getting Sued Because You're a Bad School. You're Getting Sued Because You Didn't Write It Down.
- Helen Mileto

- May 6
- 3 min read
One of the most stressful parts of my legal career was watching school leaders accidentally create massive legal exposure, not out of bad intentions, but because they were too busy running a school to think like a lawyer.
I ended up working with schools almost by accident. At my firm, a smaller shop of about 30 attorneys, I think I got placed on those accounts because I was the young female associate who could relate well to the school leaders. There were maybe ten of us doing employment litigation, but schools became my thing, and I got to know that world well. What I learned very quickly is that most school administrators are incredibly dedicated people who genuinely care about their students and staff, and who also have almost no idea how much legal risk they carry on a daily basis.
What's interesting is that after representing these schools in litigation, the relationship evolved. It turned into something closer to fractional legal support, where we helped them build the systems and documentation processes that would have prevented the crisis in the first place. That's actually how I know firsthand that fractional legal counsel works as a preventive measure. I watched it work.
Title IX was the one that kept me up at night. Most people associate it with college athletics, but it reaches much further than that. Title IX essentially gives the federal government the power to pull funding from any school that discriminates against a student, a child, or an employee in a way that violates the statute. That includes how you handle discipline, how you structure your admissions process, and how you respond when a parent or student raises a concern. If a school mishandles any of those situations, it's not just a bad day. It's potentially an existential legal threat.
The pattern I saw over and over again was school leaders reacting emotionally instead of procedurally. A student acts out, and the instinct is to make a quick decision to protect the other kids and the staff. That instinct is completely understandable, but when there's no documentation trail, no formal process for escalating behavioral issues, and no written procedure for how warnings are issued and what options are offered to the family, that quick decision can look very different under legal scrutiny.
I watched schools that had beautiful missions and strong communities find themselves defending discrimination claims because they didn't have an internal discipline procedure that could hold up on paper. The care was there, but the process wasn't, and in a legal context, the process is what protects you.
Admissions was another area where I saw schools expose themselves without realizing it. The criteria you use, the way you communicate decisions, the consistency of how you apply your standards from one applicant to the next: all of it matters. If a family believes their child was denied admission or removed from the school for a reason that touches a protected class, and you don't have clear, documented policies showing otherwise, you are in a very difficult position to defend yourself.
What I always tried to help my clients understand is that legal protection in a school environment doesn't come from being right. It comes from having a system that shows you acted thoughtfully, consistently, and with documentation at every step. The schools that invested in building those systems rarely ended up in my office with a crisis. The ones that didn't, even the ones with the best intentions, were the ones calling me in a panic.
If you run a school, a daycare, a camp, or any organization that serves children, I would encourage you to ask yourself one question: if a family challenged a discipline or admissions decision tomorrow, could you show a clear, written trail of how and why that decision was made?
If the answer is no, that's the gap worth closing before it becomes a legal problem.
If you’re reading this and thinking, “I’m not sure our processes would hold up under scrutiny,” you’re not alone. This is exactly the kind of work I support clients with through fractional legal counsel—helping you put the right systems and documentation in place so you’re not navigating these situations reactively.
You can learn more about how I work here: https://www.helenmiletolaw.com

Comments