Kimberlee Bennett ’97 is Maine’s 2019 Assistant Principal of the Year
By Marc Glass, March 2019
Kimberlee Bennett ’97 says the roots of her interest in teaching children, especially those who struggle with learning, stretch back to primary school.
In 1981, in Lincoln, Maine’s, Ella P. Burr School, Bennett’s second-grade teacher asked her to help tutor a classmate with Down’s syndrome. Bennett quickly found she was adept at and enjoyed helping Kyle.
“It was such a good connection that it lasted throughout elementary school,” she recalls. “My mom says that one day I came home and announced, ‘This is what I want to do. I’m going to work with kids like Kyle forever.’”
Kimberlee Bennett ’97, Maine’s 2019 Assistant Principal of the Year, in South Portland High School’s hall of flags, an initiative she implemented to recognized the nationalities of all enrolled students. (Photo by Marc Glass.)
Thirty-eight years on, the values that Bennett first put into action at Ella P. Burr have received broader acclaim: The Maine Principals’ Association has named her the state’s 2019 Assistant Principal of the Year.
Bennett, who has served South Portland High School’s students and families for the past seven years, says the recognition is humbling, especially because of the prevailing perception of assistant principals — as disciplinarians.
“Everybody knows what the assistant principal does. You deal with the really difficult things in schools,” says Bennett of the profession. “Receiving the award made me realize people recognized that I care deeply about what I do and the students I work with, and that it’s made a difference in their lives.”
Among her initiatives that the MPA recognized is the Hassles to Tassels program at South Portland High School, which she launched with school completion coordinator David Brenner in her first year. The after-school support group targets students identified as at risk of not graduating for myriad reasons.
“I started looking at all the seniors who were not on track to graduate, and put my head together with some people and asked, ‘What can we do?’” says Bennett.
Bennett and her team meet weekly with the Hassles to Tassels students, and, over pizza, dig into resolving their issues. In some cases, the problems call for help with homework, meeting deadlines, and time management.
“Sometimes kids aren’t getting their homework done because they have to work, and they have to work because they are supporting their families,” Bennett says. “So we might work with a business to say, ‘Can you please not schedule this student until 4:30 on Tuesdays to make sure that they have time to do homework?’ We try to break down the barriers when kids can’t access their education for a variety of reasons.”
Through Hassles to Tassels, Bennett has also changed the dynamic with many of the school’s most at-risk students.
“Some of the students who would avoid me in the hallway because they knew they had skipped class are now the kids coming up to me to say that they handed in their homework on time,” she says.
After being nominated for the honor by South Portland High School Principal Michelle LaForge, Bennett was required by the Maine Principals’ Association to seek confidential reports on her practice from students, parents, and colleagues — much like a 360 performance review. Free to choose whomever she preferred, Bennett could have cherry-picked her critics. Instead, she decided to select people, “who weren’t necessarily cheerleaders of Kim Bennett.”
“For some of the parents I reached out to, I was not always their favorite person because of the role I’ve had to play with their child. And the students that I reached out to were students who have not necessarily had the best time in high school,” she says. “I wanted the evaluations to be fair, and I wanted them to be based on the overall picture of what I do.”
Bennett, who majored in special education at UMF and began her education career as a resource teacher at Molly Ockett Middle School in Fryeburg before serving 12 years as a resource teacher at Gorham Middle School, says she was motivated to pursue a master’s in administration by an interest in improving students’ lives and schools on a programmatic, system level. At South Portland, she says she’s lucky to be part of an administrative team that includes fellow assistant principal and close colleague Chris Hughes ’04. The two Farmington graduates support each other through the job’s most harrowing moments.
“Chris and I have talked a lot about the list of things that as an assistant principal you end up having to do that you never wanted to experience,” she says. “I can no longer say that I’ve never lost a student to an overdose. We know this job is really about digging in and dealing with the hard issues, and those are the times when our students and our families need us the most.”
“We can’t always be the good guy, and when people sign on to do this job, you know that you’re not always going to be able to be the good guy,” she says. “But we learn a lot about what’s going on for our kids through conversations, and it’s stuff that we lose sleep over. Especially in times of tragedy, you always wonder, What else could I have done?”
To help keep work-related stress in check, Bennett turns to paddling — and writing about her adventures on Maine’s waters. In her book, Paddling Southern Maine, Bennett and co-author Sandy Moore offer directions and descriptions for 54 paddling adventures for those seeking to explore Maine by kayak, canoe, and stand-up paddle board. Bennett is also editor of a popular paddling-focused blog — Recreational Kayaking In Maine — and has been named one of 30 people worldwide to serve as an ambassador to Women Who Paddle, an international organization focused on empowering women to connect with each other and the outdoors through paddlesports.
In addition to co-authoring Paddling in Southern Maine, Bennett is one of 30 international ambassadors to Women Who Paddle.
Aside from providing texture to her life and an important dose of self-care, Bennett says her work with paddling — in particular a widely viewed video of her first experience on a stand-up paddleboard — has also made her more human in the eyes of her students.
“In the video, I do a face-plant on my first attempt. Some of the kids found it and enjoyed it a lot,” Bennett says. “They’ll say, ‘Miss Bennett, I saw you fall off a paddleboard!’ And I’ll say, ‘But did you see me get back up? That’s the key part!’ That’s my favorite part of the job — developing relationships with students and their families.”