WESTPORT–Next Tuesday, each Westport voter can choose up to four candidates for Board of Education. A reader wondered, “Is this an important choice?”

Consider these facts:

  • Westport Public Schools are one of the strongest magnets drawing families to Westport.
  • Westport’s education budget represents almost two-thirds of the town’s annual spending.
  • Westport Public Schools report not to the office of the first selectman, but to the Board of Education. 
  • The superintendent of schools–the town’s highest-salaried employee–is hired by and reports to the Board of Education.

The eight candidates for Board of Ed are 

Westport Journal asked each slate of candidates to answer six questions. The questions–and answers from each slate–appear below. The order of the responses was randomized.

Westport Journal: The Westport Public School system is one of the most generously endowed in the country. But we can’t afford everything. What initiative would you like to see adopted by the WPS and what would you sacrifice to pay for it?

Tolan: I am committed to maintaining a responsible budget that preserves programming and faculty while supporting innovative new initiatives. By identifying cost-saving measures, such as developing a district-owned fleet for outplaced students, expanding in-district programs to reduce outplacement costs, and leveraging artificial intelligence for efficiency and professional development, we can invest strategically without sacrificing quality. Our recent transition to the State Partnership for health insurance, which saved over one million dollars, demonstrates our ability to manage resources effectively and creatively to sustain strong educational programs, staff, and faculty.

Shackelford/Harris: With 80% of the $150 million budget locked into contractual obligations, there’s little left for innovation. That’s why our primary initiative is public-private partnerships.

These partnerships would tap into our community’s incredible resources — which include foundations, nonprofits, businesses, alumni, and families — to fund enhancements without sacrificing core programs or passing the burden onto taxpayers. 

But this doesn’t let the Board of Education off the hook. We must also be better stewards of the existing budget. That means prioritizing educators over unnecessary administration, fixing facilities problems before they become more costly, and demanding clear budget options from the district. We will do the homework, ask the tough questions, and find savings in non-student-facing areas.

Frankel, Hopson, Hordon, Zucaro: We would like to see long-overdue upgrades to our athletic facilities.  A premier school district needs premier athletics and facilities, yet ours fall far behind neighboring towns: no permanent restrooms or concession stand, no dedicated girls team locker room, no Wi-Fi access, and no field lighting beyond the Staples boys football field. 

The encouraging part is that much of this can be achieved without taking from the existing school budget.  A coordinated, district-wide parents association and community fundraising could finance key improvements while accelerating design and approval timelines.  This approach would let stakeholders directly participate in shaping the facilities our athletes deserve.  

Community members have already devoted significant time developing a thoughtful plan, but it stalled amid shifting priorities and distractions.  With clear direction from the Board, this project could move forward.  Investing in athletics is not a tradeoff against academics, but rather reflects our same commitment to excellence, ensuring that safe, modern facilities uphold the high standards we set for our academics, our students, and our community.

Harrington: If re-elected, I would focus on two major initiatives. First, the ongoing prioritization of facilities beyond Long Lots and Stepping Stones, funded through the Capital Budget. I first ran for the Board four years ago because of facilities, and while I’m proud of the progress on Long Lots and Stepping Stones, much more needs to be done. We must move forward with a new Coleytown Elementary School (CES), modernize Kings Highway School for full ADA compliance, and pursue a long-overdue renovation of the Staples auditorium. For more than 25 years, Westport has underspent on school facilities, and we can no longer afford to risk another CMS-style crisis.

Second, I want to help execute our Superintendent’s “Leadership Academy,” part of the new Strategic Plan and funded through the operating budget. It’s a bold, forward-looking idea to develop student leadership and voice — the kind of program often found in private or collegiate settings. The concept is still evolving, but the Board should partner closely with the Superintendent to make it a reality. We can identify operating savings to support these priorities. I’ve pushed for years on transportation efficiencies and believe more can be done. I also voted against the recent 4% pay increase for the Superintendent, which I felt exceeded inflation and was inconsistent with raises for our school nurses and custodians.

Westport Journal: The Westport Public School system has attracted some of the most talented, creative and forward-looking executives working in public education today. What does the next Board of Education need to do to ensure that WPS continues to attract the best educators and administrators?

Harrington: Westport is fortunate to have an exceptional team of educators and administrators — some of the most talented and forward-looking professionals in public education today. Our Superintendent deserves real credit for recruiting and empowering high-performing leaders who bring both creativity and accountability to their work.

When Tom Scarice arrived, morale and trust in the system were lacking. His most important early achievement was stabilizing the district and restoring confidence among teachers, staff, and administrators. That foundation has been critical to the progress we’ve made since. This is why I was so disappointed with several coaching non-renewal hearings earlier this year. I fully support upgrading talent and making changes — I do this all the time in my own work in New York. However,

I was very critical when some process steps were mishandled and outgoing coaches were tarnished by unfair comments from the administration. We need to learn from this — but move forward stronger. The next Board must look to the future. Competitive pay is important, and Westport has largely delivered here. But forward-looking initiatives — the Strategic Plan, placing AI at its center, and launching the Superintendent’s Leadership Academy — will make Westport an even more dynamic and attractive district for top talent.

Frankel, Hopson, Hordon, Zucaro: First, compensation must remain competitive for excellent educators and administrators.  This does not mean approving above-inflation raises like those adopted last year for the Superintendent and his large staff, but it does mean acting responsibly to ensure we remain a destination for top talent.

Creating an environment where educators and administrators are supported, trusted and empowered is also essential.  Board members must promote a culture of respect and collaboration.  Disagreements are inevitable, but they should be addressed through civil, thoughtful dialogue instead of public conflict or political posturing.  Promoting legal action or spreading false narratives about administrators on social media and in the local press has no place in responsible governance.  The conduct displayed by certain Board of Education candidates earlier this year in response to a sensitive personnel matter was inappropriate and undermined the integrity of the district.

Board members should question and challenge leadership constructively, while treating staff with dignity and professionalism that model the values we expect from our students.  A high-performing district depends on mutual trust between the Board, administration, and educators.  By modeling integrity, civility, and shared purpose, the Board can ensure Westport continues to attract, retain the top professionals who make our schools thrive.

Shackelford/Harris: We agree our executives are talented, but so are our teachers, paraprofessionals, and support staff. We just gave administrators generous compensation increases; it’s time to focus on the needs of the people in the classrooms with our kids every day.

We need more paras in elementary classrooms and more substitutes at the secondary level, and they all need to be paid better. Our middle-school teachers shouldn’t be forced to give up their prep time to cover classes.

But pay is only half the battle. The district’s own engagement survey shows declining positive results. Our PTAs hear it daily: Teachers are under-resourced and stressed. And a stunning 43% of students say they “like school.” Right now, we also leave teachers to handle parent conflicts without clear policies or support. That has to change.

Culture and excellence is our brand. To attract the best, we have to be the best place to work.

Tolan: This is a real concern; school districts nationwide are experiencing a serious shortage in qualified educators. Our administration has done an excellent job in recent years of attracting and retaining qualified, talented educators. The traditional inducements, such as competitive pay and benefits, are vital, but so are ensuring the facilities in which they work are safe, healthy and inspiring, and giving them opportunities to not just develop professionally but to innovate. 

Our teachers have engaging and active minds, and design new lessons, approaches, and courses. They inspire our students to learn and to innovate themselves, and they must have the flexibility and freedom to do so. Ongoing collaboration with faculty members, staff, and administrators is essential for new hires to our district to feel as though they belong to a supportive and vibrant learning community.  Every year, the Board interviews administrators, faculty, and staff across the system as part of our formal review of the Superintendent. (We choose whom to interview.) Educators describe a far richer and more satisfying culture than with any previous administration. 

Westport Journal: The Westport Public School system does many things very well. What can the next BoE do differently to make sure our special education initiatives are as good as they can be?

Shackelford/Harris: We’ve heard from too many families that navigating special education feels like a fight. Parents feel they have to “lawyer up” or hire private advocates just to get the services their children need.

That is unacceptable. Our first commitment is to propose a dedicated Special Education ombudsman — a liaison to help families navigate a complicated and often intimidating system.

This isn’t just about resources; it’s about culture. The BoE must set a new tone: one of collaboration, not conflict. We must stop forcing families to fight the district and instead treat every family as a partner in their child’s success. This change is long overdue.

Tolan: As a former special education teacher, advocate, and parent of children with learning differences, I believe every child can succeed when we understand and support their unique learning profiles.

After years of advocacy by parents and educators, all K–2 teachers have now received Orton-Gillingham training, the gold standard in dyslexia instruction, helping over 90% of third graders, including special education students, meet or exceed literacy standards. I support certifying all elementary teachers and expanding training for paraprofessionals, who play an important role in supporting our students with special needs. By strengthening and expanding the intensive resource room curriculum, particularly at the middle school and high school level, we can better serve our most vulnerable learners and reduce costly outplacements. I also believe in increasing opportunities for inclusion, bringing all students into the heart of our school community.

On the Board, I have supported expanding Effective School Solutions to elementary schools and increasing professional development in classroom management and emotional regulation to ensure that every student can thrive both academically and socially.

Frankel, Hopson, Hordon, Zucaro: We must undertake a fresh review of special education.  Too many families feel the district has failed to meet their children’s needs, and their concerns share many concerning themes. 

The Board should engage with local special education advocates who regularly represent parents in disputes with the district (without discussing individual cases) for better insight into systematic challenges and constructive solutions.  

We should ensure mediation is pursued early and frequently when disputes arise.  

We should ensure those with reporting obligations have sufficient and accurate guidance on when it is – and is not – appropriate to involve DCF, paired with better communication around these sensitive issues.  

We should expand on the success of ESS in delivering in-district services that keep students connected to their peers and communities, extending these supports into elementary schools.

We fully agree with Westporter Rosa Balestrino:  

“Decisions should be guided by evidence-based practices, input from parents and experts, and regular evaluations of program effectiveness. Oversight of consultants and service providers, periodic audits, and continuous improvement processes should be standard. Legal and procurement practices should be reviewed periodically to ensure cost efficiency and that educational—not legal—priorities guide decision-making.”

Harrington: Special Education has been one of my top three priorities throughout this campaign. When I first joined the Board, I deferred to others who had more experience in this area. My oldest child—now studying for a master’s degree in London—had multiple IEPs, but that was the extent of my personal experience. Through many conversations and emails with parents, I’ve developed strong conviction that we can and must do better. Many families are satisfied, but too many are not—and concerns often surface one family at a time, rather than being addressed systemically.

The next Board must take a more proactive and transparent approach. We need more resources to strengthen in-district programs, so fewer students require costly out-placements and more can thrive within Westport schools. Too many needs never make it onto an IEP in the first place—we must identify and support students earlier.

I also support creating a fully independent Special Education Ombudsman to ensure parents have a trusted advocate and consistent communication. Delivering for every learner requires courage, clarity, and accountability—and a Board willing to keep asking tough questions until every child’s needs are truly met.

Westport Journal: Fifth-grade math scores, in 2025, fell to their lowest level in at least seven years. Is the Westport Public School system doing something wrong at the elementary level and, if so, how should the next BoE direct the administration to correct the course that they are on?

Tolan: Test scores are a single snapshot of  students’ academic profiles. Yet we must continue to monitor the data to determine if a trend exists, and re-evaluate the curriculum, instruction, and gaps in student learning wherever necessary. As a strong advocate of personalized learning, I support differentiation within the classroom in addition to small group instructional models.  The primary elementary curriculum Think! Mathematics relies on a Singapore Math approach that emphasizes conceptual understanding. Over the past few years, we have been laser-focused on early literacy, and the results are impressive. We now need to do the same for math. 

Harrington: The decline in fifth-grade math scores is concerning and deserves an honest, data-driven response. This cohort began their school years just as COVID hit — and they lost almost a full year of in-person learning right as they were starting their elementary school journey. That disruption had lasting effects, but we can’t assume “time will fix this.” That’s too passive.

I was not convinced or satisfied with the administration’s response when we discussed this issue at a Board meeting last month. The next Board must take a more assertive role and direct the administration to conduct a comprehensive diagnostic review of math instruction across grades 3–6 (with a particular focus on 5th & 6th grade) — examining curriculum pacing, intervention strategies, and teacher support. We must identify struggling students earlier and ensure interventions are consistent and effective. Our teachers are exceptional, but they need time, resources, and training to succeed.

This is a perfect example where the Board and administration must look through a more critical lens — to fix one of the few areas of our otherwise successful system that truly needs focused attention.

Shackelford/Harris: Falling scores are a warning light, and the BoE can’t just dismiss the findings. We need to be proactive and dig into the “why.”

We shouldn’t be waiting for state test scores to sound the alarm. Our teachers are on the front lines; they know which students are struggling right now. The Board’s job is to ask the right questions: Are we listening to our teachers? Do they have the resources to try new approaches? What are the top-performing districts in the U.S. doing, and how can we learn more?

We will seek these answers and work with the administration to get our students back on track.

Frankel, Hopson, Hordon, Zucaro: There is little more important than helping our youngest learners build a strong foundation in math.  Pursuing faddish or unproven instructional trends and agendas distract from this core mission.  The decline in fifth grade math scores is concerning and must be addressed through evidence-based analysis.  While similar declines are consistent statewide and often linked to pandemic learning loss, Westport must take ownership of its own gaps.

We support the administration’s current efforts to focus more individualized attention on this cohort and on students who are struggling to meet grade-level.  The next Board of Education should ensure a focused, transparent and measurable plan by setting explicit math improvement goals tied to state benchmarks; monitoring progress quarterly with clear data presentations; aligning resources, curriculum, and professional learning; and partnering with the superintendent to achieve measurable outcomes.  Engaging families to sustain math confidence and consistency from classroom to home is also essential

We also believe technology can be part of the solution.  Strategic use of AI-assisted diagnostics and adaptive assessments can help pinpoint learning gaps early and tailor support to each student.  Improving math outcomes will require clear goals, strong instructional leadership, and collaboration between educators, families and the Board.  

Westport Journal: The ground is shifting under every school system in the world. AI in the classroom is in its infancy but, over the next four years, the BoE will make decisions that will have a major impact on the students we graduate. How will you help direct the administration to make sure that all of the teachers at Staples (and, to a lesser degree, our middle schools) understand and appreciate AI and guide our students to leverage it effectively?

Frankel, Hopson, Hordon, Zucaro: We commend the administration for prioritizing AI and for the thoughtful analysis recently shared with the Board.  AI will undoubtedly transform education, as with so many other areas.  However, the current plan spends undue time on issues such as ethics, bias, and the philosophical.  Although much of the technology outlined in the plan is already available, the plan doesn’t anticipate implementing AI district-wide for at least two years.  By then, the technology and its educational potential will likely have changed significantly.  

Rather than having a team of 50 educators and administrators develop a plan in an area largely outside their expertise, the district should partner with outside experts who can guide practical implementation.  We need to move incrementally and cautiously—but we need to move.  Starting small with pilot projects would allow the district to learn as technology evolves and ensure responsible innovation. 

To connect innovation to real impact, the district should enhance measurable goals and align budget line items with specific student outcomes like adaptive learning tools that personalize instruction, AI-driven analytics that reduce assessment time, and systems that improve administrative efficiency.  Impactful metrics and funding alignment would demonstrate tangible progress while ensuring every dollar advances teaching and learning.

Shackelford/Harris: We can’t be afraid of AI. The Board and administration must lead by example, demonstrating how to use these tools productively. To his credit, the superintendent has made AI one of his top priorities, and wisely looked to our front-line educators to work through the challenges and possibilities of AI.

AI is a powerful resource, but it can also be a crutch. As a Board, we can use AI to research best practices from other districts. We expect our administration to use it to make better, data-driven decisions, and our educators to use it to bring new resources into the classroom.

We will also prioritize community conversations that bring in experts to help parents and teachers navigate this new technology together.

Finally, we need clear policies. We must ask the administration for rules that distinguish between using AI as a tool for learning versus a crutch that can lead to cheating. Like all technologies, we need to teach responsible use. 

Harrington: I have been a strong supporter of our Superintendent’s Strategic Plan. Moreover, I was the earliest and most enthusiastic voice on the Board when he moved to place AI at the center of that plan. He deserves real credit for recognizing early that AI is not a passing trend but a fundamental shift in how our students will learn, create, and eventually work.

The challenge now is execution. The next Board must ensure that this initiative is fully implemented, not just discussed. That means a structured and ongoing program to train every teacher at Staples — and eventually our middle schools — to use AI responsibly and effectively.

Teachers should see AI as a tool to enhance instruction, personalize learning, and help students think critically about technology. I see too many voices focused only on ethics. I will be the Board voice championing the Superintendent to move faster and be bolder. This will unlock students’ time and drive more — not less — individual learning and opportunities for true critical thinking and discussion. I see this every day in my own workplace as a Managing Director in New York City.

Tolan: AI has the potential to reshape education. It must be implemented thoughtfully and with an unwavering commitment to human-centered learning. Protecting student privacy, maintaining educational integrity, and ensuring ethical use are non-negotiable priorities. The district’s strategic plan wisely incorporates a Code of Ethics for AI use, anchored in seven principles: human-centered, robust and safe, representative and inclusive, transparent and explainable, clear and accountable, secure and private, and sustainable. These principles must actively guide practice. AI must never replace teachers or authentic human interactions. Instead, it should serve as a tool for critical thinking, creativity, problem-solving, and research. The Board’s role is to ensure AI adoption remains intentional, transparent, and aligned with educational values rather than market trends.

After the last presentation at the most recent Board of Education meeting on October 23rd, I am intrigued to learn more about how our faculty and administrators can leverage AI to reduce time on routine tasks as well as to increase student engagement.

Westport Journal: Are you satisfied with the level of Social and Emotional Learning the Westport Public School system does? In your view, do you think there is too much SEL or should the WPS system devote more resources to it?

Shackelford/Harris: As parents, we know social and emotional learning is never done. We can always do more.

The question is, what do our teachers see, what do they need, and how can we support them? The most important partnership in our town is the one between parents and teachers. We are in this together: raising our children to be resilient, productive, and thoughtful adults.

If elected, we will actively listen to both groups and ask constructive questions. Let’s put our heads together to proactively address the social and emotional challenges our students face. Student success is job number one!

Frankel, Hopson, Hordon, Zucaro: There has been an overemphasis on SEL in recent years.  Hardly a Board meeting passes without discussion of SEL, whether through climate surveys, policies, or professional development.  We welcome the new strategic plan’s shift from SEL toward AI.  

We fully recognize that social and emotional development is essential for students to reach their full potential, and that the state mandates certain SEL initiatives.  Yet, measuring the effectiveness of SEL remains difficult, and recent climate survey results do not indicate systemic problem areas.

Supporting students’ social, emotional well-being is important, but it must not come at the expense of academic rigor.  Our mission is to ensure that every student engages in a robust curriculum with a variety of class offerings, and academic tracks that builds critical thinking, creativity, and collaboration.  We should also not lose sight of the variety of extracurricular programs particularly in the arts and athletics that naturally cultivate confidence, resilience, teamwork, and conflict resolution.  These experiences create a waterfall effect where academic rigor plus extracurriculars drive social and emotional growth.  When we prioritize academic challenge and opportunity with well-rounded extracurricular programs, we empower students to develop character, creativity, and confidence that inspires true excellence.

Tolan: Our children’s mental health continues to be a primary concern for me. Our administration has noted real changes in kids’ ability to regulate themselves. I believe, as not all current candidates do, that teaching our kids how to regulate their emotions as well as teaching broad social-emotional capacities, that is soft skills, is necessary. It is paramount not only to their ability to learn but also to their enjoyment of school.

The Board must continue to prioritize access to mental health supports, integrate social-emotional learning into classrooms, and foster strong connections between students and trusted adults.  By committing to both academic and emotional support, the district can ensure that every child feels capable, resilient, and valued. 

Harrington: I strongly support Social and Emotional Learning (SEL) when it is done with purpose and balance. Students cannot learn effectively if they are anxious, disengaged, or unsupported — and the past few years have made that clearer than ever. SEL helps students develop resilience, empathy, and collaboration — skills that serve them well beyond school.

That said, SEL should never become a substitute for high academic expectations. I believe Westport has generally struck a healthy balance. I don’t believe it has — or will — cross that line. The district’s teachers and administrators understand that strong academics and emotional well-being go hand in hand. Westport is a high-performing district — but that can come with a cost, too. I deeply believe we put too much pressure on too many students. SEL can help with this, but we also need to address the root causes of student stress and anxiety.

The new cellphone policy is a good start, but we should look further — including at workload expectations, scheduling, and the overall AP course mix — to make sure excellence doesn’t come at the expense of student well-being.

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