As Wilton High School‘s first dean of student life, Michelle Shoop has spent her opening weeks walking the halls, meeting students and listening. She wants to learn where students need help while there is still time to make their high school experience better.
That involved some reflection on her own high school experience, and she recalled how as a student she approached taking on a geometry project.
“We had to present a unit or something, and everyone in class just made a poster and was talking about it, and I was like, ‘Oh man, this is not fun,’” she said.
Instead, Shoop found inspiration in a cartoon called Donald Duck in Mathmagic Land, featuring the popular Disney character discovering the connection between math and music.
“I made a whole play to teach the concept like the movie did, and it was great, it was fun, and I was like, ‘This could be my job,’” Shoop said.
Making student life better is at the core of the new Dean of Student Life role launched by administrators this year. Shoop said she is still feeling her way around, but she is trying to be proactive in helping students adjust to high school life and stopping any problems before they interfere with the kids’ high school experience.
“Right now it’s a lot of listening and learning,” Shoop said. “I spent the first week getting my steps in and just walking up and down, first learning the building. I’m still like, which way is which?”
Shoop said she is meeting as many people as possible, getting to know students who may need support, helping maintain the school’s cellphone-free zone and meeting with groups including the Diversity, Belonging and Visibility Committee to focus on any students that need particular help with feeling like they belong. She is particularly interested in making sure freshmen get off to a great start this school year.
“I just started going to freshmen study halls. I’m just doing like a 10-minute, trying, you know, getting all their names. ‘Hey, how was your transition? How did it work out? What do you wish you knew? Do you have any questions that I could maybe answer?'” Shoop said.
Shoop came to Wilton from Amity High School, where she headed the math department. She said the newly created position appealed to her because it would allow her to work with students before concerns such as repeated absences grow into more serious problems.
“It’s a position that I’ve really been advocating for, with the growing, different needs of the new generation,” Shoop said.
Shoop earned a bachelor’s degree in mathematics with a minor in secondary education from Southern Connecticut State University.
A 2004 graduate of Masuk High School in Monroe, Shoop is an accomplished basketball player with many accolades. She is a member of the Masuk Athletic Hall of Fame and the Southern Connecticut Athletic Hall of Fame, and as a player for the SCSU team, Shoop started on the squad that won the Division II national championship in 2007. She was inducted into the Connecticut Women’s Basketball Hall of Fame in 2025.
“One thing I love about basketball is, it’s a game of mistakes where even if you make a mistake on one end, you immediately can go down and make a play on the other end and make a difference,” Shoop said.
At an August Board of Education meeting, WHS Principal James D’Amico described Shoop as energetic and full of ideas. He said her role would help strengthen programs that connect students and staff to the school.
“She is dynamic in a number of ways,” D’Amico said. “But what she’s going to do, I think primarily, is help establish all of the wonderful programs that we have that help connect students and staff to the experience here. She’s just going to figure out all that is under that umbrella, and make it stronger.”
