As a Head of School Nears Retirement, His Son Reflects on Leadership Lessons Learned

The first time I remember disagreeing with my dad was when I was 5. I couldn’t hold a pencil and couldn’t write, so my parents decided to have me repeat kindergarten. I wasn’t happy about that choice, and I made it very clear to both of my parents in a way only a sobbing, kicking 5-year-old can. They didn’t change their minds.
The first day of my second year of kindergarten soon arrived, and I sat outside on the steps wailing before school started. A new teacher at my school approached me and asked, “Are you OK?” She discerned my message through my blubbering: “My parents ruined my life.” She then asked my name so that she could call my parents to see what was happening. Jamie Piltch, I told her emphatically. She didn’t end up calling my parents—such was the life of being the head of the school’s son.
From my first day of pre-K until my high school graduation at The Shipley School (PA), I was the head of school’s kid. In third grade, when I still couldn’t write very well but could do math quickly, students complained that teachers gave me special math problems because of my dad. Who knew people could find a way to be jealous of extra homework? The older I became, the meaner the taunts were. One peer went so far as to say that my comments in class were absolutely the dumbest he had ever heard and that the teacher only entertained them because of my family. Needless to say, I wasn’t invited to many parties during my high school years.
I almost left Shipley for my junior year. I was sick of being the head of school’s son. I decided to stay, though, in large part because of how much I loved the school. It turns out that among other things, living every day with a head of school is a great way to learn some key lessons in leadership.

Building Trust 

It took me some time to see how my dad made Shipley into the school that I knew and loved, but I do remember when I recognized that his leadership style was the key. In the spring of my sophomore year, a boy who didn’t particularly like me had received a judicial board for cheating on a test. That day, he made a point of publicly saying that he didn’t trust my dad to make a fair decision—in large part because the boy and I didn’t get along.
I waited for my dad’s decision with angst. In my mind, it couldn’t end well. Either the boy would be fairly punished and use his punishment as an excuse to rail against the school more, or he would get off easy.
My dad, however, somehow punished and palliated him. The boy, a notorious rule-breaker and anti-Shipley voice in the community, later told me how much he respected my dad as a head of school. I was stunned. The reason for his positive outlook? The student didn’t walk into the office to receive a punishment from an administrator who knew nothing about him. Instead, my dad knew everything about his life—from his family situation, to his favorite classes, to his hobbies. They talked about the offense in the context of the parts of his life that were most important to him, an approach that built trust and a sense that my dad made a thoughtful decision rather than an arbitrary one.
The more I paid attention, the more I saw how well my dad understood everyone at Shipley on a personal level, and how that created a sense of community and trust. He knew all 850 students’ first and last names, who their parents were, and their respective neighborhoods. He could name every member of every sports team and theater cast. When he saw people in the hallways—no matter young or old—he would address them directly. He never acted as if he were too important for anyone or as though he didn’t need to develop relationships to get his work done. He saw his connection with people as the key to his guiding Shipley effectively.

Bringing Community Together

His personal investment in and knowledge of every teacher, student, and staff member became particularly important during times of crisis. After I left for college, two students in the Shipley community passed away within a year. Both were kind, generous, and thoughtful. And because of his close relationships with the school, my dad knew both incredibly—and painfully—well.
In private, I saw my dad’s tears. I listened to him pray for the parents and think about the school. And in public, I saw much of the same. His willingness to be vulnerable in those moments—to be like those who were hurting—was key to comforting Shipley. While his sadness made him human, he also didn’t let his own grief cloud his ability to do what was needed. He organized memorial services when the parents couldn’t, and he reached out to the siblings of the students. He helped ensure meals were sent to the families’ homes and wrote public letters to the community about the importance of cherishing those around us.
In one letter he wrote, “While we would prefer that tragedy and loss did not occur, our ability to acknowledge situations and to be there for our families, each other, and others in the greater world, define who we are. By doing it together, we will help ourselves, our children/students, and the community.”

Making It Personal 

Now, as a recent college graduate considering my own career, I’ve had a chance to reflect on my dad’s excellent leadership. He never acts as if he’s above anyone else, regardless of school hierarchy; he knows people and makes thoughtful decisions within the context of who they are; and he allows himself to be human in hard moments while remaining a steady guide for those who need it.
Reflecting on my dad’s tenure at Shipley, which will come to an end in June 2019 after 27 years, brings me back to those first days of kindergarten. Roughly six weeks into the semester, the teacher asked for a meeting with my parents. She told them that my second year of kindergarten simply wasn’t working. I cried every day and refused to play with my classmates while making it very clear to anyone who would listen that my previous class had been a better one. Out of concern for both my classmates and me, my teacher raised the idea that perhaps I should move up to first grade so that I could be back with my friends.
My mom, who normally remains even calmer than my dad, was moved. She wondered aloud, “Steve, maybe we made a mistake?” He turned to her and said, “Sunny, take the long view.”
Almost 20 years later, I can confidently say, he made the right choice to take the long view that day. He thought about what was best for me and didn’t personalize it when I told him he ruined my life. That approach isn’t just a good way to parent. It turns out that it’s a pretty effective way to run a school, too.
James Piltch
James Piltch

James Piltch is a recent college graduate and will be working as a research assistant at the Harvard Kennedy School next year.


Joyce Sherry
2/6/2019 1:49:07 PM
James, I agree with the other comments. What a lovely piece. As a Baldwin alumna, I saw the Shipley name and read eagerly on. Maybe old allegiances (and rivalries) die hard, but I freely acknowledge that your moving reflection served as both a tribute to your excellent school (and its Head) and as great guidance for those of us in school leadership positions. Thank you!

Pam Clarke
9/12/2018 11:46:48 AM
Jamie: What a lovely piece! I've followed your Dad's tenure at Shipley because he is a great man and because I graduated from Shipley in 1962. He has always talked with pride about his kids, and one can certainly see why - many thanks for a great letter.

Jim Dunaway
5/7/2018 12:20:48 PM
Very nice piece, Mr. Piltch! Thank you. My daughter put up with being the assistant head's child for 10 years, then a year-and-a-half in another school as the head's daughter. Though she would say it all worked out, she did write on her page in her senior yearbook, "Dad, I love you, but you have worked in every school I have attended. Please don't follow me to college!" I promised her I wouldn't.

Malcolm Gauld
5/2/2018 6:17:38 PM
Great piece, James. Fifty years ago this year, I enrolled In the secondary school where my father was head of school (founding head, in fact). You brought me back to those days. Initially, I was not keen on this arrangement. Like you, I I owe a lot to my dad for his efforts to make it work. In the early going, he pulled me aside and said, "You don't embarrass me... I won't embarrass you." Truth be told, I doubted that he would hold up his end. Then, about a month into that first year, I found myself on a bus with football teammates returning from an away game. We were engaging in typical teenaged banter when someone referred to me by my last name. At that point, one of my teammates said, "Wait...are you related to the headmaster?!?" You might appreciate why that simple question made my day. That was the moment when I began to accept that my peers were going to accord me an identity distinct from that of "headmaster's kid."

Way back then, I never could have imagined that I would become head of school at that same school 20 years after enrolling. Then, during my tenure in that role, my own two daughters enrolled, each spending four years during my watch. I tried to emulate my dad's approach with me and it all worked out. Thanks for sharing your experiences. I plan to pass your story along to my daughters.

Mike Albritton
5/2/2018 11:29:30 AM
What a lovely essay, James. I respect your father's leadership, and I appreciate your ability to navigate tricky circumstances and come out the better. All of us who bring our children to the schools where we work hold our breaths and make a delicate choice: Will this work? Will our children be better off for our decisions? I suspect many people, in large and small ways, made the circumstances tenable for you and your dad. I know I am grateful to the teachers at my school who didn't hold my imperfections against me when they dealt with my sons. There is a level of decency and respect and knowing that your experience calls us to emulate in our own schools. Thank you very much for sharing your thoughts.

Matthew Stuart
5/2/2018 10:34:13 AM
What an incredible tribute to your father, and an inspirational message for me as a leader. Unless I enroll my two cats (one of whom has some serious learning issues), neither a child nor I will experience your challenges. I can, however, relish the fine and helpful leadership thoughts. I met your dad in 1999, while I was a Klingenstein Fellow at Columbia Teachers College. He made a strong impression then, and I am glad that Shipley (and his son) continued to thrive.

Stuart Hirstein
5/2/2018 10:26:54 AM
Thank you for sharing this! Our daughter is a junior at my school and has experienced many of the same things you have shared. I have forwarded your reflection to her. Thank you!

John Palfrey
5/2/2018 9:58:56 AM
What a wonderful reflection on your family's experience, Jamie -- thank you for sharing it. I am among the many admirers of your dad's leadership. I am also forever indebted to him as my first college squash coach. He gave me a chance to work my way onto a national championship team when he didn't have to. That experience makes all the things you write ring totally true to me. Coach Piltch knew each one of his players just as Head of School Piltch does, too.

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