Half a century on the Hill: Assistant Head of School Tom Perryman shares his experiences at Greenhill

When Tom Perryman ‘81 began his education at Greenhill, Lyndon B. Johnson was president and the Vietnam War was in full swing. Half a century later, Mr. Perryman remains deeply rooted in the Greenhill community, and his love for the school has only grown over the years.

“When I was about three years old, my mother decided I needed to get out of the house. And so they searched for the right fit and I ended up at Greenhill,” Mr. Perryman said.

He enrolled halfway through the school year in 1967 and remained at Greenhill until he graduated in 1981. As a student, he played football and baseball and captained both sports his senior year. His favorite subjects were English and History, and he admits that he wishes Greenhill had put more of an emphasis on the arts when he was a student.

After leaving Greenhill, he attended Northwestern University and majored in English. Shortly before receiving his English degree an opportunity came knocking. After he graduated from Northwestern in 1989, he returned home with a job as a seventh grade English teacher at Greenhill.

“Mr. Phillip G. Foote was the Head of School at the time and was a real mentor of mine. He called me up in December of my senior year in college and I had no idea what I wanted to do then,” Mr. Perryman said. “I’d done no career planning when he said, ‘I think you should think about teaching. I have a Middle School English position. Let’s talk about it.’ So I decided to give it a shot.”

While he may have had his doubts about teaching at first, Mr. Perryman noted it only took a couple of weeks to dispel any sort of hesitance moving forward.

“Within a couple of weeks, I was hooked. I still remember my first sixth grade advisory. I [can] name them all and see them all in my mind. I still run into them from time to time and I’ve had lunch with a couple of those kids who are now 43 years old,” Mr. Perryman said.

This was the first job offer he received and it would set a precedent for the rest of his career. Moving forward, he never applied for a job and has only ever been asked to take a position.

After six years teaching in the Middle School, he decided he needed a change and assumed the Head of Lower School position in 1990. When Philip Foote retired in ’92, Mr. Perryman moved into the Admissions department. Peter Briggs came in as Head of School, and under Mr. Perryman’s tutelage, Greenhill began to focus on diversity and finding a greater balance between arts, athletics and academics.

“From ‘93 to ‘96, we really focused on bringing in students of color, student-athletes and student-artists who could really triumph,” Mr. Perryman said.

In 1996, Mr. Perryman took the Assistant Head of School position.

“Peter Briggs realized he needed a right hand man that could reach out to people,” said Mr. Perryman. “His history at the school and consistent need to reach out to others was instrumental in connecting the teachers with the administration. “

Mr. Perryman continued working as the Assistant Head of School until 1999 when he left Greenhill for a brief two-year stint and attended a seminary where he said he wanted to “wrestle with hard questions.” He returned to Greenhill in 2001, per Mr. Griggs’s request.

“It was then that I realized my ministry was with kids. I had a passion for teaching kids,” Mr. Perryman said.

Today, Mr. Perryman remains Assistant Head of School and teaches one English course each trimester, which he says is his favorite part of the day. Having been at Greenhill so long, he admitted to getting “that itch” again when asked what the next step was.

“I don’t know what I do next. I’ve never planned my career. And so I’m starting to think, what do I do next? I’m trying to find some way to make a new difference in the world and I have no idea what that’s gonna be,” Mr. Perryman said.

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