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Superintendent's Updates

Superintendent's Update

Good afternoon,

It gives me great satisfaction to provide an update to our school community that is not directly related to the pandemic.  In fact, I find it quite exciting and energizing to provide an update to the community about the potential future of our schools and how we can best serve our students in preparing them for the dynamic world they will enter when they graduate.

Following my entry to the district last year, and in partnership with the Board of Education, the district initiated a long-term strategic planning process.  Although this process was delayed due to the restrictions of the pandemic, today, I would like to provide an update on that process, including where we’ve been and where we are headed. 

The general purpose of strategic planning is to set priorities, focus resources, align and strengthen operations, and to ensure that all stakeholders are working toward common goals, with an established agreement around intended outcomes.  This disciplined approach produces fundamental decisions that shape and guide what an organization is, what it does, and why it does it. 

What inspires me most about this process is the bold contemplation of “what could be”.  Long-term planning provides an opportunity for a school system to press reset, and to thoughtfully redefine the work we do in serving our students in order to prepare them for the complex world they will confront as young adults.  This is our opportunity, an opportunity to scan the horizon and project what our schools could be.

Where We’ve Been
Prior to my tenure which began on July 1, 2020, I drafted a one year strategic entry plan with six objectives ( for the Board of Education which was intended to support the leadership transition process, while addressing other timely areas of interest (i.e. reopening the schools, reopening CMS, expanding diversity, equity and inclusion efforts, and improving district communication).  Ultimately, the objective of gathering stakeholder feedback in this initial entry plan was intended to serve as a prelude to a long-term strategic plan.   

Although the pandemic halted many of these efforts throughout the year, as the pandemic’s impact began to recede in early spring, it was time to pivot to engaging stakeholders in order to initiate the long-term planning process.  This process began in May with an initial inquiry and synthesis stage, highlighted by hosting a series of focus groups.

Over a period of nine full days, I met in small groups with a total of approximately 50 individuals at each school and the Stepping Stones Preschool, an aggregate total of over 400 faculty, support staff, parents, and students.   This significant investment of time was worth every minute as I gathered critical insights while beginning the process of developing professional relationships with a wide range of stakeholders. 

I asked a set of core questions for each group. In short, the questions were an attempt to surface: assets and strengths to build from, features of the professional culture that hinder or accelerate performance, priorities for long-term improvement as seen by individual stakeholders, and areas of stress for students.  The full written summary that I provided to the Board of Education on July 22 with a synthesis and analysis can be found here:  

Where We are Headed
On September 8 I provided the Board of Education with an overview of the timeline for the next 4-6 months in developing the district strategic plan.  I have captured the anticipated monthly highlights below for all members of the school community.

September 2021
During the month of September the district will assemble a core group of professional educators to lead the planning process. I will identify a core team of 18-24 faculty and administrators and convene the first organizing meeting in September to clarify roles, responsibilities, and tasks/timelines for the planning process. Additionally, in order to test and verify and ensure that my analysis of the focus group findings is accurate, and to also provide an objective perspective to the process, the district has secured the services of retired superintendent and consulting strategic plan facilitator, Judith Wilson ( 

In her first efforts, Judith will conduct one on one 15 minute virtual interviews with each Board of Education member, central office administrator, and building principal.  In addition, interviews will be conducted with a representative sample of curriculum coordinators, district administrators, faculty, and parents with the assistance of the district PTA  in order to provide our consulting facilitator with a district overview, while learning the values and priorities of some of the key members of the school community.  

October-November 2021
October and November will be busy months.  Following the spring focus groups, and the one on one interviews, Ms. Wilson will administer broad surveys to students in grades 5-12, parents of all students pre-K-12, and all employees.  These surveys will be designed to test and verify my interpretations of the spring 2021 focus group findings, and the values/beliefs established in the district 2017 strategic plan.  It is expected that surveys will be administered by October 22. 

Perhaps most exciting in this process is a series of "education summits'' that I plan to host in October/early November.  These summits will require the attendance of the core team, while providing in-person access for the entire Westport community to observe and participate in a large setting.  The purpose of these summits is to host experts (i.e. "futurists") in the field of projecting major trends and factors that will shape the worlds of work and citizenship over the next 10, 20+ years.   A keynote address, followed by an interactive question and answer/fireside chat, will engage all of those in attendance. This work will inform overarching goal development and specific strategic objectives of our plan.  In short, this will be a time for the community to project the future, and to “reenvision” the work of our schools today in order to prepare our students for a dynamic and complex world. 

The core team will convene in November with our consulting facilitator to formulate the first iteration of 3-4 overarching long-term district goals, along with targeted strategic objectives, for the district’s priority work in the next 3-5 years.  The team will use key understandings from the “Education Summits”, current and relevant research, and observations of other findings (i.e. survey data verifying focus groups findings, existing district data sources, etc.),to ground their work. The team will also begin to identify measures and initiatives/action plans which will flesh out more discrete and specific efforts in subsequent meetings

December 2021
The Board of Education will be presented with this first iteration for its consideration and endorsement in early December.  Following Board deliberation and support, I will appoint a pair of co-chairs for each strategic objective developed in the process. Their responsibility will be to lead a small group of educators in further refining and establishing the development of individual initiatives/action plans.  Additional initiative/action plan committee members will be recruited to assist in implementation and monitoring.

January - March 2022
It is expected that by mid-winter, Initiative/action plan committees will design the first 18 months of work on each plan.  Upon completion, the action plans will be presented to the Board, staff, and community for consideration.  Finally, in addition to updates during the development process, an ongoing communication plan will be designed in order to keep the strategic planning work, implementation, and monitoring at the forefront for everyone in the Westport community.

I strongly encourage all members of the school community to stay engaged with this process as it unfolds.  I will provide updates along the way.  This is a most exciting time, a time for boldly considering what our schools can be, and what the next level of performance is for our schools. I look forward to helping to lead the district through this planning process.

Thomas Scarice
Superintendent of Schools 

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