The two candidates for the job of Martha’s Vineyard Regional High School principal, Sara Dingledy, principal of Westchester Square Academy of New York City, and David Williams, former principal of York Middle School in York, Maine, each spent one marathon day last week visiting the school, talking to students, sitting down with the school committee, and interacting with the community.
A third finalist, David Fabrizio, current principal of Ipswich Middle School, dropped out of the running for the job last week.
Mr. Williams visited on Thursday, and Ms. Dingledy on Friday. The visits included a 90-minute question-and-answer session with the small group of residents who turned out for the open public session.
In her remarks, Ms. Dingledy spoke about providing an inclusive and supportive environment for students, and her love for the Vineyard community.
Mr. Williams emphasized his passion for instruction, including in the classroom, and his immediate availability to move here.
Following the interviews, Superintendent of Schools Matt D’Andrea said he will review feedback from students, staff, parents, and the community.
“It’s very important that I get your feedback about how you feel about Sara, or if you were here yesterday, about Dave,” Mr. D’Andrea told the group Friday. “I would appreciate hearing from all of you.”
Group members were asked to fill out an online form. Once he reviews the feedback, Mr. D’Andrea and a “small, representative contingent” will visit the current or former schools of one or both of the finalists. Mr. D’Andrea will make the final decision following those site visits. The assistant superintendent of schools and head of the search committee, Richie Smith, said he expects the decision on the next principal will be made in early February.
‘Hit the ground running’
Mr. Williams said his strength is in instructional leadership.
“I really believe sincerely in principal as principal-teacher, especially if you’re going to provide instructional leadership,” he said. “You have to be able to lead by example.”
He said that could mean teaching a class once he’s settled into the job. In York, he taught a STEM enrichment class.
“It did wonders for staff culture and staff morale, because I do have really, really high expectations for teachers, and I am unapologetic about that,” he said. “For me to be able to get in the class was sort of putting my money where my mouth was, in that sense.”
His education career began on the ocean. “I’m sort of a maritime guy,” he said. “Before I got into teaching, I did underwater research on lobster and crab populations. I had a chance to do some outreach work there with high school kids, and decided I wanted to be a biology teacher.”
He said York is a community similar to the Vineyard, in that it is glamorized as a vacation spot.
“At the end of the day, when the summer crowd moves, it’s a place that’s sustaining itself economically on tourism and lobstermen,” he said.
If hired, he would begin by meeting with all the constituencies from within the school, he said, similar to how he started in York. That formed the basis for a school improvement plan.
“I invited them in to schedule a one-on-one meeting with me,” he said. “I met with everybody. I met with food service. I met with the custodial staff.”
One parent questioned how long it would take to see change.
“I firmly believe this: If you have major issues in the building and you don’t address them right away, what you’re essentially doing is sanctioning mediocrity,” he said. “You will feel a tangible change immediately. I come in and inject a sense of energy and belief structure that you will see and you will feel immediately.”
As a principal in York, he wrote a newsletter to parents every week, started a blog, and added a feature on the school website that allowed parents to directly ask him questions that he would either answer publicly or call the parent to discuss. “That kind of transparency with the community is critical,” he said.
He spoke of the importance of goal-setting for students. He said students should be able to articulate their success in relation to goals, rather than just assignments.
He also stressed student engagement. “I engage with people on every level; I’m out there with kids, I’m in the classroom, I believe I should be the first one greeting them at that door,” he said. “I have strong beliefs and strong visions about how schools should be run. The kids will know me.”
Mr. Williams openly addressed the questions raised about his arrest by York police for operating while under the influence. “I think it’s important that you hear it from me, and I wish that there were more people here to hear it, because if I was on the other side, I would certainly want to know,” he said.
Mr. Williams said he had dinner with his mom and some friends in Portsmouth. “I had a few drinks at dinner and made a poor choice to drive home,” he said. “It was the worst mistake of my life, and it still haunts me.”
He called his superintendent and school committee chairman, and “fortunately they were both very supportive,” he said. The following Monday, he met with all 600 students in the building.
“What I said to them was, What do I say to you when you make a poor choice and wind up in my office?” he said. “You need to take responsibility for your actions, you need to own it, and you need to find a way to learn from it. It’s the belief system that you cannot let your failures define you. I tried to embody that for my kids.”
He finished the school year, and eventually made a personal decision to take a year off. That means he is free to move to the Vineyard at any time, he said.
“If I am fortunate enough to be the one this community selects as the next principal, even though my contract might begin July 1, I’m not currently working, so I’m down here right away,” he said. “I can observe throughout the spring, and I can shadow Peg [Regan] here in the building. I would love to shadow at the elementary schools and meet the eighth graders, go to sporting events, start studying the policies, and really hit the ground running July 1 rather than coming and scrambling in the summer.”
‘Underpromise, overdeliver’
Sara Dingledy grew up in Connecticut, but has been working in the New York school system for 17 years. She said she believes in the work-team model.
“Don’t make it so things all are filtered through the principal, but create routines and structures so that teachers know what the expectations are, know what the values and the culture are, and can solve and address some of those issues themselves,” she said.
She also values educational leadership, and empowering teachers.
“I philosophically believe, in terms of educational leadership, that I serve the teachers so the teachers can serve the kids in the best way,” she said. “That said, I’m a teacher at heart; I love being in the hallways; I love being in classes; I like talking to students.”
At her current school, she implemented two afterschool periods of professional development for her staff each week, to work on achieving specific goals and working together to address problems. She also started an afterschool advisory session and community-building time for students.
She said discipline in the school should be based on defining values and figuring out what policies and cultural aspects are important.
“In New York, there’s a mandate on behalf of the parents and kids to keep order in that school, so that’s a huge, relentless piece of my job,” she said. “Because of that, there’s a clarity around that and enforcement quality that I think I’ve gotten really good at over the years.”
She said she strives to graduate students who can recognize and show gratitude, have a sense of optimism, find ways to be kind, deal with frustration, and reflect on personal goals, in addition to core academic skills.
One parent asked how Ms. Dingledy would address disenfranchised students.
“There are ways you can still make high school joyful and connecting and engaging for students, even if they’re not finding academic success,” she said. “I think relationships really matter, and talking to students really matters, and making sure you’re creating systems and staffing models that recognize that not all students will be bought in.”
She recognized there are some differences between her current job in the Bronx and the Vineyard position, although the size — 600 students — is similar. She said there’s an anonymity granted in her current position.
“The ironic thing is, people are like, Oh New York, you’re probably used to the politics and this and that, but there’s like a thousand principals in New York, so there’s an anonymity,” she said. “You just do your work, you do the job … Kids travel from one community to the next, so there’s not that same community investment in the school, for good or for bad.”
But that’s also part of her interest in the job. She comes to the Vineyard with her family to visit her uncle once or twice a year, she said. She remembered a specific conversation she had with her husband while at the Niantic Park playground with their kids.
“We were there and I remember just having this conversation like, We love this, we love the feeling, we love the community, we love how we feel up here, think about all the opportunities,” she said.
She sees the Vineyard as a good place to raise the children, ages 3 and 4, but she also saw moving her family here as the biggest hurdle. She said her husband is currently employed in New York, and would have to leave his job to move to the Island.
“It’s one of the person’s lives that’s moving, and the other person is coming along; that’s probably been the challenge that many people have faced,” she said. “It’s sort of a three-to-one option, where we think it’s great for the kids and for me, so I think he’d be willing to take the leap of faith.”
In fact, it was his idea in the first place, she said.
At the end of the community session, she gave a brief closing statement.
“I will say that my big thing is that it’s a big jump — what I do day to day would be very different if I were to come here,” she said. “There’s no perfection in this work. I like to underpromise and overdeliver, and part of that is that there’s not a recipe or a system or a plan that you can come in and drop in. I’m very cognizant of that. It’s a process, and that’s what I like about the job.”
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