Imagine that you are the dean of the upper school at a K-12 day school along the rolling hills above the Pacific Ocean. Your school’s students come from the wealthy enclaves of the Valley, children of producers and actors and sports stars. There are many similarly expensive day schools in the greater Los Angeles area, and the competition for students, for excellent teachers, for donations is constant. These concerns are not in your day-to-day purview, but you are aware of them.

Imagine that your head of school has recently hired a well-spoken, enthusiastic 24-year-old to teach ninth-grade English. She has a master’s degree and a passion for literature. She wants her students to memorize sonnets and analyze song lyrics and discuss Dickens fluently. If a student doesn’t do the reading, she is noticeably impatient; if an essay is subpar, she edits and grades accordingly. She likely means well, but as many novice teachers do, she conflates her high expectations with high performance.  

When a parent complains that her daughter feels singled out and picked on by this teacher, you meet with her to hear her side of the story. She is surprised, somewhat indignant, and defensive. Ultimately, you agree with the parents that her classroom is not the right fit, and you move the student to another section. The student happily completes her four years at your high school. The teacher leaves after a year.

Seeing the Big Picture

The story above is true. And it’s one that heads of school face, in variations, every year. Oh, and as you may have guessed, that teacher was me.

Did the dean of the upper school know how humiliated, confused, and hurt I was? Probably not, and my humiliation eventually faded. As my teaching experience morphed into a legal career working for and advising independent schools, I came to understand that the situation transpired exactly as it should have.

The student had a legitimate concern, it was addressed in the best way for the student, and likely the head of school herself never even knew about it — nor should she have. Novice-teacher me had no idea of the myriad incidents that make up a school’s big-picture operations. School-lawyer me understands that there are some issues and outcomes for which someone is always going to be unhappy — perhaps litigiously so — but if you do the right, honest thing, the school can move forward with confidence and in fulfillment of its larger purpose.

For example, what if the dean of the upper school had insisted that my ninth-grader stay in my classroom? Her parents’ complaints may have escalated to the head of school. They may have even withdrawn the student. This effect would have ricocheted among admissions, development, possibly communications. The head of school’s attention would be directed away from other pressing obligations. In fact, looking back, the only thing school-lawyer me would advise the dean to do in the spirit of teacher retention and growth would be to give novice-teacher me a mentor who could advise me on ways to inspire and influence less-than-responsive students in a more positive way. 

Fulfilling Purpose

Having worked at a school, I know the issues that can keep heads of school awake at night: school safety, sexual misconduct, student mental health. If a head empowers her staff with the policies and procedures to act confidently, then a parent’s request to move a student to a different English section shouldn’t be one of those sleepless issues. Likewise, even with these big issues, if a head can feel confident that her policies and procedures are legally sound, up-to-date, and well-communicated, maybe she can sleep a little better — and this is my job as the school’s attorney. In my current, private practice, I know that by helping to shoulder the burden of these large issues, administrators can lead, teachers can teach, and students can learn — and the school can continue to move forward, day after day, fulfilling its purpose. 

But I’m also aware of the smaller pressure points that can lead to larger issues if not addressed: parents who have concerns about accommodations, or disciplinary decisions, or travel abroad programs. Business office concerns about contracting or tax filings. Or employees who feel they have not been treated fairly. When unaddressed, even these myriad small issues have an impact on a school’s ability to serve its greater purpose of educating students. I hope my inexperience as a teacher decades ago informs my current advice to administrators — I know professionally and personally which issues can be handled before they become legal ones.   

Naïve, idealistic 24-year-old me wanted to educate students through unbridled passion and high expectations. I did love teaching, but I also learned that a school was not only about me, the person at the front of the classroom. A school community is supported by an infrastructure of physical facilities, financial planning, and human capital. I am still passionate about education, and my goal remains the same: to support an environment of learning and growth. But now I do it through policies instead of poetry. And it’s just as fulfilling.