Carlin Hart is already settling into his new job as principal of the Oak Bluffs School. In an interview at his office on Wednesday this week, he took a seat among boxes and books, some of them his, some belonging to outgoing principal Laury Binney.

But he will spend his first official day of school with the students, some of them familiar faces from his tenure as assistant principal at the Oak Bluffs School, where he worked from 2001 to 2008. Others will be unfamiliar, and he’ll make his introductions accordingly. But one very important student, a first-timer entering kindergarten, will surely stand out in the crowd. Unlike other kindergartners, Kailyn Hart will share her first day of school with her dad.

It’s not the first time Mr. Hart will walk school hallways with one of his own children. When he was offered the position of assistant principal at the Martha’s Vineyard Regional High School, the first person he consulted was his son, Patrick, who was a high school junior that year.

“He was like, ‘seriously?’” recalled Mr. Hart of his son’s reaction, channelling the voice of a horrified 16-year-old boy.

But in the end, Patrick decided he didn’t really mind, as long as his father agreed not to embarrass him too much.

“Just don’t sit with me in the cafeteria,” Mr. Hart remembered his son saying. “So the first couple of days I went over and sat with him in the cafeteria.”

Patrick recovered, and is now headed off to West Point in the fall. And Mr. Hart had the honor of handing his son his high school diploma on the graduation stage in May, before he realized it would be one of his last acts as high school assistant principal.

Mr. Hart said his younger daughter has had a somewhat different reaction to the news that he will be working in the same building where she will be learning to read and write in September. She’s ecstatic.

“We’re going to have lunch every day, and she’s going to come in here when she wants to come in here,” he said. “She’s got all kinds of plans.”

Mr. Hart’s experience in the school system dates back some 20 years. Born in Fall River, he attended schools there and after high school moved south to play baseball at George Mason University in Fairfax, Va. Upon graduation, he decided to stay in the South and began working in the Fairfax County public school system in 1990. He spent time as a physical education teacher, a third and fourth grade teacher and a health teacher before becoming an assistant principal in the Fairfax district. A year later, he responded to an advertisement for an assistant principal job on the Vineyard, and moved up with his wife, Katie, son Patrick and their daughter Jenny. Despite being born in Massachusetts, he had only visited the Vineyard once. “It was huge,” he said of the transition. But he said he was thrilled to leave behind memories of heavy traffic congestion on the Capital Beltway outside Washington, D.C.

Mr. Hart’s plans for the coming year center around opening up lines of communication among school employees. He remembered sessions held with the former principal Mr. Binney each morning, when he was assistant principal in Oak Bluffs. “Every morning at seven o’clock we were in here. It was us and it was the guidance counselors, Monday through Friday. A little powwow every day talking about what’s going to happen today, what happened yesterday, what’s going to happen next week,” said Mr. Hart. “I thought it was very effective. It kept you in the loop,” he said.

He said he’ll continue those meetings as principal, but will also approach teachers and other employees for feedback and ideas.

“Decisions shouldn’t just be my decisions. I’m the kind of principal that I want to get some input. I’ve been gone for two years, and these folks have been here,” he said. “By talking to people and getting out there and talking to the teachers, they’ll tell you what you need, [and] what they need in order to be successful. And if I’m in here and not out there, then I’m not going to know.”

He said he hopes his experience as interim principal of the Oak Bluffs school, in 2007-2008 while Mr. Binney was away on a year-long sabbatical, will give him a leg up on the new job. “That year started off rough. There were some personnel issues that I had to deal with right away,” said Mr. Hart. He remained tight-lipped about the details of the infractions, saying only that one related to a financial issue, and the other to a staff issue. But he said being “thrown right into the fire” has prepared him for what may be a challenging first year.

For starters, MCAS test scores among students at the Oak Bluffs School have fallen short of state requirements in past years, a problem Mr. Binney appeared to be making headway with in recent years. Mr. Hart said because other Island schools tend to produce better test scores among students, he’ll look to those teachers and administrators for guidance. “If they’re not passing, if they’re not reaching the bar on that MCAS test, then we’ve got to figure out why,” he said of the Oak Bluffs students. “Why are other schools having success and why are we not having success? What are they doing that we’re not doing? So we’d have to talk to Tisbury, talk to Edgartown, talk to West Tisbury.”

And he said the solution may turn out to be quite simple. “We don’t have to reinvent the wheel. There may be something that they’re doing, that’s real simple, that we’re not doing. And we need to try it out,” he said.

But he worries about the fact that the state keeps setting the bar higher for MCAS scores. “Obviously we want the MCAS scores to be good, but it’s not all about the MCAS scores, and it shouldn’t be all about the MCAS scores,” he said. “It’s just extra pressure, and the target just keeps getting harder and harder. I just don’t think it’s realistic.”