In the public eye: WMS principal instrumental in creating learning environment for students

Editor’s Note: This is another in an ongoing series of Windham and Raymond town employee profiles.

By Ed Pierce

A school principal plays a crucial role in fostering a positive and productive learning environment and Greg Applestein is certainly proof of that.

Greg Applestein has served as the principal
of Windham Middle School since July 2023
and is dedicated to finding ways to help
struggling students and celebrating the
successes of WMS students.
PHOTO BY ED PIERCE 

Applestein has served as Windham Middle School principal since July 2023 and takes his leadership role seriously.

“Maintaining a good balance between the work I do with the students and the work I do with the staff is one of my biggest challenges,” Applestein said. “Anyone who works in education is always working in a world where there are multiple and competing priorities. And on any given day, all of them are just as important as any one of the others. So being able to analyze, synthesize, and evaluate said priorities such that I can act on them in a timely manner, which lead to satisfactory outcomes for all is definitely one of my biggest challenges.”

Among his duties as WMS principal, Applestein is tasked with ensuring the safety and security of all students and staff, to continually help WMS improve in our areas of need in all that they do with and for the students, and to be compassionate, responsible, and respectful with and to all students, staff, families, and community members in helping them to achieve their full potential.

Applestein enjoys his work and says interacting with the school’s students and staff on a daily basis is the best part of his job.

“Over the past 35 years, I’ve been in four other schools, in four other districts, in four other parts of Maine and I get to spend my days with the best students, staff, families, and community members in all of Maine,” he said.

According to Applestein, the greatest misconception that people may have about his job as WMS principal is that school administrators only meet with the students who are in trouble.

“For me, the more time I can put into developing and maintaining good working relationships with all students proactively, the more positive and upbeat my relationships with students will be,” he said. “I spend some time each week meeting with students to let them know how well they are doing and how proud we are of them.”

Born in Philadelphia, Pennsylvania, Applestein’s father served in the U.S. Air Force, so his family moved around a lot when he was in elementary school. When his father retired from military service, the family moved back to Pennsylvania when he started sixth grade and Applestein lived there through college.

He attended Indiana University of Pennsylvania and earned a Bachelor of Science degree in English Education in May 1990. He went on to obtain a master’s degree in educational leadership from the University of Southern Maine in May 2012.

Applestein taught English and Video Productions for 22 years at Belfast Area High School and then served for three years at Ellsworth High School as assistant principal and worked for five years as assistant principal at Scarborough High School. Prior to joining Windham Middle School, Applestein was the principal of Bonny Eagle High School for three years.

“I knew RSU 14 had a great reputation due to its students, staff, families, and community members and that was one of the many reasons I applied for this position,” he said. “Secondly, I had heard and read about all of the school renewal which was occurring in this district and the work resonated with me and my core values and beliefs. Thirdly, I have always wanted to work at the middle level as middle level students are energetic, honest, and experiencing rapid growth and development over these three years. I always thought I would like working with this age group, and I am humbled, blessed, and grateful to be serving in this role.”

His most memorable moments while working for WMS occur when students are recognized for upholding the school’s core values.

“We host a grade level Community Meeting at the end of each of the four marking periods in the year. In our Community Meetings, staff give ‘shout outs’ to students who did a variety of things well during the marking period,” Applestein said. “And the students are recognized for upholding our core values of Compassion, Integrity, Respect, and Responsibility. These have been very memorable moments because our students are recognized, honored, and valued by our staff and students and I’ve never met a student who couldn't benefit from all of that.”

He says the most important thing he’s learned while working for WMS is that there’s a very palpable feeling of community, collaboration, and a can-do spirit which all permeate the hallways, classrooms, offices, courts, and playing fields of WMS. <