“Where We Stand”: Board Of Ed Candidates On Oversight Of Superintendent

An informed electorate is the greatest bulwark of democracy.

Westporters understand this is a very important election. “06880” is doing our part, to help Westporters understand candidates’ perspectives on a variety of issues.

Once a week, between now and Election Day, we’ll ask the men and women running for 3 important boards — Selectmen/women, Planning & Zoning, and Education — one specific question.

We’ll print their responses verbatim.

This week’s question for the Board of Education is:

There has been a great deal of discussion recently about the relationship between the Board of Education, and the superintendent of schools. What is the proper balance between following the superintendent’s lead, and providing oversight?”

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Two Democrats will be on the ballot as petitioning candidates, having secured over 400 signatures. Jodi Harris and Stephen Shackelford say:

The relationship between a Board of Education and a superintendent is a partnership, not a rubber stamp. The superintendent’s role is multifaceted. He has numerous managerial responsibilities (including ultimate responsibility for a large staff), but he also should be the district’s visionary leader, challenge assumptions, and propose bold initiatives to move our schools forward.

The board’s role, as the elected voice of the community, is to ensure that vision is thoroughly vetted, financially sound, and easily measured for maximum impact.

Stephen Shackelford and Jodi Harris.

Finding this balance requires mutual respect, transparency, and a shared commitment to excellence. But effective oversight is not passive agreement. A board that simply “gets out of the way” abdicates its primary responsibility to the voters and taxpayers who elected them. Unfortunately, we’ve seen this happen all too often.

Too many board meetings have featured major proposals approved with minimal questioning from the majority, despite valid concerns raised by the community and even other board members. This lockstep approach is not healthy governance. It fails our students, our educators, and ultimately our superintendent.

A case in point is the prolonged debate over the Staples cellphone ban. While we support the goal, the process revealed a flaw in the system.

For over a year, the administration advocated for the ban without presenting a detailed implementation plan or budget, despite repeated requests from parents, teachers, and students. A proactive board would have insisted on answers to crucial questions: What is the impact on curriculum? What technology alternatives are needed? What are the costs? What success metrics will we use to determine effectiveness? Instead, these questions were largely deferred. A board exercising proper oversight would have demanded a complete plan before the discussion could advance, ensuring a smoother, more successful rollout.

This pattern of reactive governance has other consequences. A lack of motivated questioning and failure to demand transparent processes has preceded controversial personnel decisions and costly lawsuits that have consumed district resources and eroded public trust.

Rigorous oversight is not about micromanagement; it is about foresight. It’s about asking the hard questions, and insisting on actual answers before moving forward, so we can achieve the best outcomes and avoid negative consequences in our schools and community.

A well-functioning board is also one that brings issues to light that the administration may have missed, or not properly prioritized. Part of the board’s job, as the democratically elected officials responsible for our school system, is also to serve as a key point of contact for Westport voters (and other stakeholders) with concerns about our schools. We’ve heard too many stories lately of concerns being raised to the board and then completely ignored or minimized without any real explanation, let alone discussion.

Let us be clear: Our goal is not to obstruct, but to strengthen. We are running to be constructive partners. A board of independent thinkers, willing to engage in robust and respectful debate, will challenge the administration to bring forward its best, most well developed ideas.

True leadership welcomes accountability. We believe a better balance is possible. One where the board and superintendent work together, with healthy debate and transparent decision-making leading to superior results for our entire community and a restoration of trust. We are confident that we can work constructively with Superintendent Scarice to continue to accomplish great things for Westport’s schools.

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Republican Party-endorsed candidates Dorie Hordon (incumbent), Michelle Hopson, Andy Frankel and Kaitlin Zucaro say:

The relationship between the Board of Education and the superintendent — and the administration more broadly — is central to this election.

Under Connecticut law and Board policy, the Board sets policies, goals and objectives consistent with its mission.

The superintendent and school staff are responsible for implementing those policies, managing operations, and advising the board on key decisions. And as an employee of the board, the superintendent is accountable to the board and subject to its oversight. Simply put, the superintendent follows the board’s direction, not the other way around.

From left: Michelle Hopson, Dorie Hordon, Kaitlin Zucaro, Andy Frankel.

As for Superintendent Tom Scarice, like most Westporters, we are supportive of him and the administration overall. Mr. Scarice is an intelligent, proactive, and thoughtful leader. He is well regarded by faculty, staff and the community. The educators around him are also talented and dedicated.  While we may not agree on every issue, Westport is fortunate to have Mr. Scarice as superintendent.

Where improvement is needed is not in the selection of a superintendent, but in the leadership of the board. We want to help Mr. Scarice do the best job he can, but under clear direction, consistent oversight, and with firm accountability.

Our criticism of the incumbent majority falls into 2 main categories: engagement and focus.

Lack of engagement. Being supportive of the administration is one thing, but being overly deferential is not how the board should function. The board must ask tough, informed questions, debate issues openly, and hold the administration accountable for measurable results.

Over the past 4 years, we have seen a reluctance by many board members to speak up, challenge assumptions, or propose practical solutions. Westport deserves a board of independent thinkers who can work collaboratively but are not afraid to lead and who can actually get things done.

Lack of focus. The board’s mission is to prepare all students by fostering critical and creative thinking and collaborative problem solving through a robust curriculum delivered by engaging and dedicated educators.

Unfortunately, the current Board has not consistently guided the administration toward these priorities. Instead, too much attention has been diverted to initiatives such as intrusive climate surveys or short-lived pedagogical fads like “design thinking.” While reflection and feelings have their place, we cannot lose sight of the fundamentals of teaching and learning.

That said, just as the board should not be overly deferential, electing individuals who harbor undue hostility toward Mr. Scarice and members of the administration would invite chaos, instability, and more distraction.

Recent events illustrate the danger of crossing that line. The controversy around the non-renewal of soccer coach contracts became unnecessarily divisive and damaging to the district. False accusations were made against the Staples High School athletic director. Multiple administrators were subjected to insults and ridicule, including the superintendent, athletic director, and Staples principal Stafford Thomas, and there have been calls for their firing.

Westport’s schools need steady, responsible leadership regardless of political party, and without personal vendetta or attacks. We agree with 3r Selectwoman Candice Savin’s observation that, “Board members should ask tough and thoughtful questions…But when that thorough vetting is used as a crusade to advance the special interests of specific families above the greater good…to undermine the effective leadership of the district, something has gone awry.”

It’s time to restore balance and focus to the Board of Education. Our mission is clear: set strong policies, demand results, and support the superintendent and staff in delivering the highest quality education for every Westport student. That requires leadership rooted in accountability, collaboration, and common sense.

Let’s get back to the business of improving our schools—together.

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Robert Harrington (incumbent) was not endorsed for re-election by the Republican Town Committee. He is running as a write-in independent candidate. He says:

After 4 years on the Board of Education, I believe our schools deserve leaders who ask hard questions—not those who simply go along with decisions.

I’ve worked to be a member who shows up, listens, and puts students and families first.

As I seek another term, my pitch is simple: fewer tough questions and less accountability if I’m gone. Easier for the chair or superintendent — worse for Westport.

Robert Harrington

A board that only praises itself or hides its criticism isn’t serving the people who elected it. Accountability doesn’t happen behind closed doors.

The heart of this election, and what many residents are asking, is about balance: What’s the right relationship between the board and superintendent? In my view, the answer is clear. The superintendent runs the schools day to day, but the board must provide oversight, not a rubber stamp. Respect and collaboration are vital — but so is independence.

Unfortunately, party politics undermine that independence. The official Democrats represent the status quo and a vote for no change. The official Republicans seem more focused on replacing Lee Goldstein than on offering real solutions.

I know Dorie Hordon has been asking tough questions — but will the others? Recent statements from the Republican slate sound cautious and deferential, nervous about being critical of the superintendent and administration.

During this year’s Republican selection process, I was asked if I could “tone it down.” I politely declined. My outspokenness on local issues — and toward my own party — may have cost me a nomination, but I believe that candor is exactly what Westport needs on its BOE.

This year I’m running as an independent and unaffiliated “write-in” candidate.

There were 2 clear issue this year where the BOE just rolled over — and go to the very heart  of this question:

First, the Board voted to extend the superintendent’s contract early and award him a 4% raise — larger than what our nurses and custodians received. That was a bad look for both the board and the superintendent.

Second, the Staples soccer coach hearings exposed serious flaws in process and transparency. I have no issue with a superintendent changing a coach — that can happen for many reasons — but I do have a problem when a false narrative is created and someone’s character is unfairly attacked. The board wasn’t allowed to see all the evidence or hear key witnesses. Oversight only works when the board has access to all the facts.

Over the past 4 years, I’ve tried to make accountability real:

• Pushing back when the Republican Town Committee nominated a more extreme slate of candidates I couldn’t support. I’m paying the price this election cycle.
• Questioning and voting against the superintendent’s pay raise.
• Demanding that administrative investigations be more thorough and transparent.
• Leading early efforts on redistricting and transportation savings, even when initial support was low.
• Advocating for facility improvements beyond Long Lots — celebrating progress there while also pushing for a new Coleytown and modernization at Kings Highway.

That’s the kind of board member I’ve been: independent, transparent, and accountable. Westport should expect no less.

To be clear, Westport’s schools get many things right. Our teachers and students consistently excel, and our district and superintendent have much to be proud of. But true strength comes from self-reflection. A high-performing district should also have the confidence to be critical when necessary.

Westport deserves a board that values independence over partisanship, and accountability over comfort. I’ve supported Democrats, Republicans and independents when they were the right person for the job. I’m doing so again this time.

The best boards don’t follow the Superintendent’s lead blindly — they walk beside him, eyes open, asking tough questions on behalf of the community. That’s the leadership I offer.

Jodi Harris, Stephen Shackelford, Dorie Hordon and myself represent real change for Westport’s BOE.

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Democratic Party-endorsed candidate Abby Tolan (incumbent) says:

By law, the board oversees the superintendent, the budget, policy, vision and strategy, and overall success of our schools.

 As a board member, I must trust that our CEO has a clear vision, communicates effectively, and maintains strong relationships with employees and the community.

Unlike a company focused on profits, our mission centers on unique, human students. The superintendent needs to create a supportive environment and hire strong educators. The board must hire a superintendent whose vision and philosophy align with community needs and evaluates his performance regularly.

Abby Tolan

That’s the simple answer to the question, but, picking up on things I have heard this election season, I will elaborate:: 

Budget: Its evaluation by our board and submission for approval to town bodies is arguably our most significant task. After months of deliberation and revision, the board presented the budget to the Board of Finance, several RTM committees, and then the full RTM, where at every juncture it received unanimous approval. We had tough discussions over staffing requests: 2 assistant principals and a facilities coordinator. We ultimately voted against all 3. I voted with the non-partisan majority against the assistant principals but in favor of the coordinator. You win some, you lose some: that’s the nature of  democracy and budgeting.

Capital plan:  Our capital improvement plan is light-years ahead of where we were before our superintendent’s tenure. We’re building a brand-new Long Lots School and Stepping Stones Preschool, addressing envelope and mechanicals of every building, and getting approvals for major projects, including the Staples auditorium, girls’ athletic facilities, and Bedford Middle School science labs. It’s been a signature accomplishment of this board.

Everybody wants to prioritize their projects, but we have to prioritize for the sake of our educational community and our taxpayers. Our oversight of the superintendent and collaboration with town funding bodies will lead us to deliver well-maintained, modern facilities for generations.. 

Trophies and locked gates: When the board raised these issues; the superintendent fixed them after careful consideration. The locked gate between private yards and Staples was resolved after a walkaround with the superintendent, police, 2nd selectwoman, school facilities, and RTM representatives/parents. We may not be able to respond to every social media eruption in an instant, but we do the work thoughtfully and get the job done.

Transparency, accountability, governance: This board has held the superintendent to account on budgets, phone-free schools, strategic planning, and transportation. There is no “rubber stamp.”

The board should though, for the most part, support the superintendent’s work and vision, because if he does not achieve community standards, it is our responsibility to hire a different school leader.

We are transparent: budgets, contracts, policies, curriculum are all published; meetings are noticed and recorded; there is more public comment than any school board I’ve seen. The superintendent and board are a governance team, working together closely, to deliver a high-performing district. The proof is in the pudding: unanimously approved budgets, strong capital plan, test scores, college acceptances, course offerings, extracurriculars, school culture. 

While we strive for continuous improvement, Westport is the envy of school districts nationwide.

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Click here for last week’s “Where We Stand” Board of Education story.

Click here for the first “Where we Stand” Board of Education story.