WINDHAM – After 34 years of traveling early each morning to his job leading the Windham Middle School, Hal Shortsleeve, who was hired as a guidance counselor the same year the middle school opened in 1977, has decided to retire as the school’s longest-serving principal effective June 30.

The 60-year-old Shortsleeve, who has taken one sick day in his three-decade career, entered the school year thinking it may be his last, and struggled to make the decision. But with his wife, Terry, already enjoying retirement after a 35-year teaching career and the school in good position with recent praise as a high-performing middle school, Shortsleeve figured the time was right to join his wife – and his bees, Christmas trees and blueberry crop – in retirement at their 1820 Standish farmhouse.

The hard-working Shortsleeve, who founded and shaped Windham youth soccer and junior high soccer starting in 1978, already knows he’s going to miss the children, teachers and community connections, and as such is already talking about substitute teaching occasionally in retirement. It would be appropriate since Shortsleeve started as a substitute at Bonny Eagle High School while working toward his master’s degree in administration at University of Southern Maine.

“Arriving at this decision was very difficult,” Shortsleeve said. “I really struggled with it because I enjoy it here tremendously. It’s a wonderful staff. Windham has been a great community to work in. I always appreciated the confidence that the Windham community had in me to allow me to continue to be their middle school principal for so long. I’ve never wanted to leave. I never looked for another job.

“That’s one of the things I’m proud of, that my entire career was right here in Windham – 34 years,” he continued. “And to be 30 years as principal I feel very proud. I saw a lot of changes, been part of a lot of changes, and I feel good about where Windham Middle School is right now.”

The biggest challenge of his career was the 1993 transition to the middle school concept, in which students were grouped in teams and the school population shifted from grades 7-9 to 6-8. Though difficult, Shortsleeve said the changes helped improve cohesiveness.

“Up until then, middle schools kids fell into a ‘are they K-8, or are they 7-12?’ So what happened was the middle school began to be recognized as a distinct level of education and we began to adopt the thinking that went along with that, in regard to how you organize your kids, how you team your teachers, the kinds of programming,” Shortsleeve said. “We became more student-centered rather than subject-centered, and our eighth-graders were a better match for our fifth-graders than ninth-graders were with our sixth-graders. That really changed the comfort level.”

The man who hired Shortsleeve as the junior high guidance counselor in 1977 was then-Principal Gary Moore. Moore later became superintendent, and in 1981 promoted Shortsleeve to the middle school principal’s position.

“He is among the hires I am proudest of,” Moore, who owns land in Standish but lives in Cumberland, said when contacted this week. “He’s a tremendously competent and dedicated person.”

Moore remembers the job interview with Shortsleeve in 1977, as Shortsleeve was developing the new soccer program at the junior high school.

“I remember asking if he wanted the job and he said, ‘I’d love to do it, but I’d like to continue being the soccer coach for the first year at least.’ That is an example of how extremely dedicated Hal is to whatever he sets his mind to,” Moore said.

Colleagues are going to miss Shortsleeve as well. School secretary Linda Eastman has worked with Shortsleeve since 1988. “It’s going to be quite different with out him, he’s been here for such a long time,” she said.

Eastman became most impressed with Shortsleeve’s ability to command a group of students.

“He’s a great public speaker. Without notes, he can go before a large group and speak eloquently. He also has the ability to quiet a room just by raising his hand,” she said.

On a personal level, Eastman says Shortsleeve is especially good with kids requiring discipline.

“He can calm a difficult child to a place where they can deal with what’s happening,” she said. “He is a rock.”

The school’s guidance councilor, Barbara Clark, who has worked with Shortsleeve for 24 years, says Shortsleeve “has, over the years, influenced the lives of about 18,000 students, plus or minus 225 staff members. His heart has always been focused on what’s best for children’s learning. He will be sorely missed and never replaced. Hal Shortsleeve is Windham Middle School.”

Language arts and history teacher Cathy Langis, who has worked with Shortsleeve for 15 years, said he “supports staff amazingly” and “sees the school with clarity, all three grades.”

And, echoing the sentiments of his teachers, sixth-grader David Bearor even wrote a letter to fifth-graders telling them “how Mr. Shortsleeve is a really good principal,” he said. Shortsleeve granted Bearor’s request to start an after-school video gaming club this year, which impressed the 12-year-old.

Disappointed he’s leaving, Bearor said, “I wish he could be here for next year’s fifth-graders, but I guess when he’s worked for 34 years, that’s a pretty long time.”

Even the introduction to the job description in the classified ad for the position praised Shortsleeve’s service: “The Windham Middle School principal is retiring after a long and distinguished career,” it read.

So what advice would Shortsleeve leave for the next principal? From what his co-workers have said about him after learning of his impending retirement, it turns out the advice is reflected in his own leadership philosophy:

“My advice to the next principal would be to really enjoy the middle-level child. There are a lot of people who find it a little scary to work in a middle school, but to really embrace that you’re working with what I feel is the most critical juncture in a child’s life and to understand that,” Shortsleeve said. “They come in here as students in the midst of puberty and they leave here as emerging young adults. And that’s an exciting time. I really enjoyed being part of that. I think a new principal really needs to understand that.

“I also feel good about the people I’ve hired,” he continued. “We have tremendous teacher leadership in this building. I would say the new principal really has to nurture that, to allow the teachers to grow as leaders and that’s how change happens in a school.”

Windham Middle School Principal Hal Shortsleeve, shown here on Tuesday with his longtime secretary Linda Eastman, is retiring effective June 30 after 34 years as an educator in Windham. (Staff photos by John Balentine)