Principal Gary Karlson settles in at Riley Avenue

When Gary Karlson was little, his aspirations were to be to become a Navy pilot and a catcher for the New York Mets. Although he did not achieve his ambitions for various reasons, he did find a place where he could serve.

“I always loved school,” said Mr. Karlson, who became principal of Riley Avenue Elementary School this year. “I was very fortunate to have great teachers, great administrators, right through high school. And so it was always a place that I felt very, very comfortable.”

Mr. Karlson has spent every one of his 25 years with the Riverhead school district in its elementary schools, first as a teacher at Phillips Avenue Elementary, then at Roanoke Avenue before moving up to Aquebogue Elementary School as an administrator. After a brief stint as an assistant principal at Roanoke, Mr. Karlson landed at Riley Avenue.

It didn’t take him long to settle in and get started helping everyone address their needs.

“Things occur in different proportionality at the schools, but the issues are the same. And the mission is the same,” he said. “It’s not necessarily about learning how to be a solid administrator at Riley Avenue. It’s about helping people with what they need help with.”

It’s important to Mr. Karlson that he models transparency and directness to both staff and parents. It’s this authenticity that allows parents and staff to put their trust in the school.

“We get to have really frank conversations. All the relationships are about as direct as they get and they’re about as real as it gets,” said Mr. Karlson. “I believe in high agency paired with high accountability. I do think people do well when they are in the driver’s seat, as long as we have a culture that matches that, that we’re going to talk about how it’s going, like almost all the time, and not be afraid to change it.”

One of the ongoing problems in schools across the country is chronic absenteeism, which can be a difficult and sensitive issue to address. To combat attendance issues at his schools, Mr. Karlson reframed the approach as promoting attendance rather than dealing with absences. 

“Those felt like different things with different strategies. When I came here, one of the first things we did is form an attendance team. The parent-facing communication and the ways that we engage teachers are some things I’m really proud of,” Mr. Karlson said.

When Karlson began his career, it was Bryan Miltenberg, now principal of Aquebogue Elementary School, who made him his first official hire as a teacher at Phillips Avenue in 2001.

No matter which building he is in or in which position, Mr. Karlson brings his brand of gentle listening and kindness to bear on the administration at Riverhead schools. He hopes to leave Riley Avenue better than he found it, and that his time there makes him better, too.

For anyone considering a leap into educational administration, Mr. Karlson believes there is a litmus test for success in the field.

“There’s only one ingredient that you need, and it’s kind of like the go, no-go on being administrator, and that’s can you approach situations with benevolence?” he said.

“Can you, the harder the situation with the family, can you keep in mind that they’ve got a real problem, that they are trying to get a real solution to it? You might approach it differently than them, but they are just trying to be everything they can be for their kid,” he continued.

“With the staff member, when they come in and they have a need, the reason they’re discussing it with you is real. If you can’t do that, you’re just going to be very unhappy.”