School Superintendent James Weiss retires from a place in the sun to a seat on the beach

This year, Mr. Weiss’s school vacation won’t end in September.

One week before his retirement and still hard at work, Superintendent of Schools James Weiss reflected on his career in a conversation with The Times. — Photo by Michael Cummo

For the first time in his 46 years as an educator, newly retired Martha’s Vineyard Superintendent of Schools James Weiss can look forward to an unending school vacation. On Monday, June 29, as students squirmed through a half-day at school and then began their long-awaited summer vacation, Mr. Weiss finished his 10th school year at the helm of Martha’s Vineyard Public Schools (MVPS). That Wednesday he started his first day of retirement.

Mr. Weiss spoke with The Times in his office amid his busy end-of-the-year schedule, about the decade he spent at the helm of the Island’s Superintendency Union No. 19. His responsibilities included the Island’s six public schools, which operate as five separate political entities: the Edgartown, Oak Bluffs, and Tisbury K-8 school districts; a regional K-8 school district for the up-Island towns of Aquinnah, Chilmark, and West Tisbury; and a regional high school district.

“I’ve been a superintendent for 26 years, 10 of them here, and this has clearly been the best job I had,” Mr. Weiss said, in his characteristically upbeat and cheerful manner. “And it’s because of the people. People really band together when there’s a crisis. People will step up to the plate and do what needs to be done, and I find that very refreshing and very important. So from that point of view, this has been a great place to work for 10 years and finish my career.”

A self-professed beach lover, the well-liked and respected superintendent received a gift basket of beach-related items to enjoy in his retirement from Oak Bluffs School, as well as a new beach chair from the high school class of 2015 at their graduation ceremonies, which he attended. He said he’s already tried it out.

“I’m ready to sit on the beach and not do anything else,” Mr. Weiss said. “A couple of people have said to me, Are you going to be an interim someplace; are you going to do consulting? And the answer is no.”

Mr. Weiss said he plans to take the first year of retirement to travel a bit and figure out what he is going to do next.

“But it won’t be anything to do with schools,” he added. “First of all, I’ve done enough, and it’s time. Secondly, I certainly wouldn’t do it here. Other people are going to do that, and I don’t want to be in their way. And I have no real desire to keep going.”

The highs and lows

Asked what he considers some of the high points of his Vineyard career, Mr. Weiss said three things came to mind: changes to elementary-level mathematics and the beginning of honors algebra; the addition of a nursing-assistant program at Martha’s Vineyard Regional High School (MVRHS); and a move by all the schools to add enrichment programs.

“We’ve done a lot of things to push our kids, and I think that’s a good thing,” he said of the enrichment programs. “We also at the same time have added a lot of supports — remedial teachers — and I say those two together, because really, what we’re trying to do is teach every child. Not just the ones in the middle; the students who are at the top, to get them accelerated learning, and the ones who are struggling, to get them some support.”

Mr. Weiss said he is also proud of the connections the MVPS made in the community with organizations such as the YMCA and the Sharks baseball team, as well as community partners such as the Island Grown Initiative, the Yard, and Felix Neck.

The growth of shared-service programs is another highlight, he added, such as the Bridge Program for students with autism-spectrum disorders and communication and social-interaction disorders, Project Headway preschool special education services, and social skills classes.

And if he could snap his fingers to instantly change something that has been the most challenging and frustrating for him these past 10 years?

“You’re sitting in it — this building,” Mr. Weiss answered, without a moment’s hesitation. The current superintendent’s offices are housed in a cramped, deteriorating former church, built 90 years ago, at 4 Pine Street in Tisbury.

A warrant article sponsored by the MVRHS school committee and town selectmen and finance committees asked voters at town meetings Island-wide in the spring to approve borrowing $3.9 million to fund the design and construction and to equip and furnish a new administrative building on the high school’s grounds. The article failed to achieve unanimous approval in all six towns.

“I understand that we didn’t do a good job of marketing it this year at town meetings, and there were lots of other things on the warrants, but this building doesn’t work,” Mr. Weiss said.

“We’ve had people who are handicapped who can’t come in; it’s a real problem. And the HVAC doesn’t work; the electrical system doesn’t work; there’s no confidentiality or privacy. It really has been a struggle, and we haven’t gotten very far. That’s a real disappointment.”

Lessons of a decade

When asked what he considers unique about the Vineyard’s education system, Mr. Weiss said after attending town meetings and school graduations Island-wide, what stands out for him is that the small Island’s six towns are so very different.

“And you know that, sure, there are going to be differences here, but the amount of difference, the amount of challenge in some of these communities, is really surprising,” he added. “And the whole notion of, ‘We can’t give up our school, we can’t give up what’s special to us, and work together,’ makes it difficult.”

Mr. Weiss said although most of school budgets go to fund personnel, some savings could be achieved through efficiency if schools were willing to put aside their differences and collaborate more. “I think the notion is beginning to take hold, but it will take some more time for it to actually happen,” he said.

When asked what he has learned over his last decade as an educator, Mr. Weiss said he believes schools still have a very important role to play, but that educators have to be very careful about how they make decisions.

“There is too much testing; there’s too much focus on what happens next, and not enough on the child and where he or she is at that point in their life,” he said. “We talk about teachable moments, we talk about age-appropriateness, and some of that gets lost in the shuffle. And that’s too bad. I think we’re pushing kids too fast and too hard. And that takes a toll on kids.”

Mr. Weiss said children today have psychological issues they didn’t have in the past, because the pressures are greater.

“That does concern me,” he said. “That hits teachers and school committees, and administrators as well, because they have to provide for it. But it’s the kids who take the brunt of it.”

Passing the torch

Mr. Weiss announced his plans to retire more than a year ago. He submitted his letter of retirement to the All-Island School Committee (AISC) last fall in order to allow ample time for a search process.

The AISC subsequently appointed a committee representing educators and Island stakeholders that conducted a nationwide search. Two of the three finalists selected were Island candidates, assistant superintendent of curriculum and instruction Matthew D’Andrea and Oak Bluffs School Principal Richard Smith, who were named superintendent and assistant superintendent, respectively.

Asked what advice he might give Mr. D’Andrea, Mr. Weiss had three suggestions: to set his own tone and expectations; to remember that the job is a people business, both kids and adults; and not to lose contact with the students he is supposed to work with and support.

The last piece of advice is one that Mr. Weiss put into practice many times over the past 10 years, as an enthusiastic and supportive presence at countless sports events, team and club fundraisers, plays, concerts, science fairs, spelling bees, and many other student extracurricular activities. He also made it a point to send personal letters to students commending them for their achievements and participation in various activities, as well as cards and notes to his office staff, administrators, teachers, and school personnel.

Knowing he would be retiring, Mr. Weiss said, last September he started documenting the tasks he does on a regular basis as part of his job, as well as things he does as a matter of personal style, such as dressing in costume on Halloween for visits with elementary students.

“I don’t expect anybody else to do that, but I want the next person to know I did that, as a reference in case there are any questions,” Mr. Weiss said.

“I’m fortunate because Matt and Richie both are on the Island,” he added. “Since they’ve been appointed, we’ve been talking a lot, and going through a lot of things, trying to shift some duties to them so they can experience the craziness that is Martha’s Vineyard sometimes and the wonderful things that are Martha’s Vineyard.

“In lots of ways I’ve really fallen in love with the Vineyard,” Mr. Weiss said at the interview’s conclusion. “I’m going to stay here, and retire here, and enjoy it in a different way.”