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Olga Peters/The Commons

Lyle Holiday is retiring after a long career with the Windham Southeast Supervisory Union, most recently as superintendent of schools.

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WSESU superintendent reflects on a long career

Lyle Holiday will retire in June after three years as superintendent and a professional lifetime in the school district

BRATTLEBORO—School Superintendent Lyle Holiday loves education.

Politics? Not her happy place.

“It was a very hard decision,” said Holiday of her recent decision to retire from the role of superintendent after three years serving the Windham Southeast Supervisory Union (WSESU). She leaves her job on June 30.

“I want to be right up front: I love my job and I love the people that I work with — the teachers, the administrators, and the staff — that has really been the thing that’s made it hard to decide what to do,” she said.

Holiday started her career in the district almost 40 years ago as a student teacher. In the decades that followed, she has served as a classroom teacher, as the supervisory union’s curriculum coordinator, and most recently, as the superintendent.

“When I started, we were in the throes of Act 46 and I feel like I’ve shepherded us through those Act 46 waters,” Holiday said of the divisive state education reform legislation designed to restructure and simplify the administrative structure of local school districts.

Most of her work over the past three years has focused on shepherding schools in Brattleboro, Dummerston, Guilford, Putney, and Vernon through the school governance mergers of Act 46. Vernon voted not to join the new Windham Southeast Supervisory District (WSSD) during the Act 46 process in order to protect the town’s history of school choice.

This new includes schools in Brattleboro, Dummerston, Guilford, and Putney.

With the first major consolidations complete, and her confidence that the WSSD is strong and in the hands of a capable board, Holiday said it’s time for her to make way for a leader with fresh ideas and new perspectives.

Still, the decision comes with mixed feelings.

Holiday reaches for a tissue.

“Definitely, I’m going to miss all the people I’ve worked with — my colleagues and my peers,” Holiday said.

A political education

“If this job were really, totally about education, I really think I’d be here for much longer,” said Holiday, who admitted that the political nature of the superintendent job caught her by surprise.

“I really, really love education,” she said. “And this job is really more about politics, and that was a big surprise to me.”

Holiday gives the impression that the political side of the job — maintaining relationships with leaders at multiple levels, from the state, local governments, and the community — took her farther away from what she loves the most: education.

“One of the hard things for me is I really believe as educators, we can’t be too political in our jobs,” she said. “We need to be able to be open to every viewpoint and make sure that students are the ones that are determining what they believe in.”

Yet, Holiday does admit that a part of her is political. The decisions about who will leads the country, state, and local community are important to her.

“We have an election in another year, and if I want to be able to be publicly involved with that, I can’t be tied to a position like this,” she said.

Holiday stressed she has no intention of running for office, but she said she plans to back both national and local candidates.

Supporting teachers

Holiday regards supporting new teachers as a professional responsibility.

“As an educator, you never forget your first year teaching. Never,” she said with a laugh.

She believes it’s important that experienced teachers, administrators, and superintendents work together to create an environment where all teachers feel supported and continue to learn.

Holiday said her learning curve has never ended — that each time she changed jobs, she learned a new and equally rewarding skill set.

As a classroom teacher, she learned to work with children and meet their respective needs while teaching a curriculum to the overall group.

Holiday said that watching students grow and achieve new skills has been “very rewarding.” So has her role in a child’s journey in learning to read.

“Teaching, it doesn’t ever get boring,” she said, adding that even when she taught the same curriculum from year to year, the students and their needs would always change.

As a teacher, Holiday chose to work with younger children because she loved to witness their big leaps in learning. She believes all teachers should have time to visit other classrooms as a form of professional development.

Holiday recalled a continuous process of learning during her career in education.

When she became the curriculum coordinator, she moved to the supervisory-union level and learned to train adults. She learned to think beyond a single classroom and to consider the needs of students in the whole district.

With the curriculum coordinator position also came with evaluating research and best practices that could help the most students.

The role of superintendent came with the need to learn even more skills.

For example, Holiday said that when people — teachers, parents, administrators, students — who are interacting with the academic hierarchy come to meet with her, they haven’t achieved satisfaction at the previous levels. This means they arrive at her office angry and frustrated. Holiday said she has learned new ways to stay calm and centered while trying to help people who start that conversation already in deep frustration.

But her latest job also came with new relationships with the community.

She worked with first responders to build school-safety protocols, a process she described as “scary.”

“But they are so committed to ensuring that our schools are safe,” she said.

Eyewitness to changes in education

One major thing has changed in the decades during which Holiday has served as an educator: the education.

A deeper professional understanding of how kids learn has contributed to some of these changes. Other changes, however, have been necessary to meet the needs of changing families and — all-too-often — the stressors they face.

“That has been a huge shift in the last number of years. It really is scary to me that there are students who will see things that I will never see in my life,” she said. “And that’s bothersome.”

“I can remember in my classroom every family was a two-parent household. Every child went home to a house,” she said looking back at her early career. “And that is not anywhere near a given anymore.”

In her career, Holiday has seen schools take on social responsibilities, serving students and families in ways that go well beyond reading, writing, and arithmetic. She gives the impression that teachers will still always step up to the plate regardless of the challenge.

“And that’s why I have such respect for teachers in the classroom, because they’re seeing those kids every single day and working their hardest to make sure, at least during those school hours, that kids are warm, kids have food, kids are loved.”

The shift in families and society became acutely noticeable approximately five years ago, she said, around the time the district hired its first family liaison professional with a background in social work.

Holiday believes the school district’s efforts to become trauma-informed has added a supportive safety net for all students.

Such practices not only make for more stable homes and families — they also carry over into improving education by supporting teachers, she said. As an example, teachers are trained to keep themselves calm when faced with their students’ emotional or physical stress.

“Because really we are trying to work together in our communities and do what’s best,” she said. “And when we’re doing what’s best for our families on a broader level, then we’re doing what’s best for our students as well.”

Staying steady and consistent: invaluable for others

Brattleboro Union High School Principal Steve Perrin first met Holiday when he taught one of her children at Dummerston School.

“I never saw her ‘mama bear’ side, but I think it would scare me,” he said.

Perrin described Holiday as a “subtle leader” compared to her predecessor, Ron Stahley, who seemed happy to be out front of issues in the public.

In contrast, Perrin said Holiday always presented the school board and administrators with information and helped them come to their own conclusions.

“I’ve loved how calm she is,” he said, adding that she has an amazing ability to consider issues from students’ perspectives.

He believes Holiday’s calm and steady presence is ultimately what got the district through the Act 46 merger process and helped administrators keep their sanity.

But, he said, “I hope they remember her for more than just that she was the superintendent who got stuck with the Act 46 transition.”

“She’s a lot deeper than that,” Perrin said.

One of Holiday’s initiatives that has influenced how Perrin leads is the creation of a more-uniform teacher-evaluation form and process.

Perrin said that principals routinely observe teachers to see how they are doing in the classroom. Holiday took this routine and standardized it in a way that allows a principal to collaborate in a way that better supports them, but also the teachers in their schools, he said.

Dummerston School Principal Julianne Eagan became curriculum coordinator after Holiday was hired as superintendent.

Holiday “really trusts teachers and students,” Eagan said, citing her enthusiasm and support for creativity and innovation in the classroom.. “She really trusts the people doing the work.”

Eagan added that she often sought advice from Holiday, who she views as someone able to see multiple points of view.

Education runs at a fast pace, Eagan said — it’s easy to get lost in the business.

Holiday, however, make a deliberate point to evaluate ideas and problems from different angles. Eagan has tried to incorporate the same practice into her leadership style.

“She wants to keep the focus on students, and she wants teachers to feel that’s where their focus should be,” Eagan said.

Andy Paciulli, former principal at Academy School in West Brattleboro, now serves as the WSESU’s mentor for new principals.

“[Holiday] is a very steady force,” he said. “She’s very up-front. She is pretty steadfast and deliberate.”

In Paciulli’s opinion, school administrators need such qualities from their superintendent.

“Education is highly regulated and prone to initiatives” from the federal, state, and local governments, he said, pointing out that a steady superintendent who sets a clear direction, is consistent, and can stay the course ensures that administrators don’t become lost in a sea of these initiatives.

Paciulli said Holiday helped protect the students’ learning process by effectively balancing administrators between where they needed to focus on learning and where they needed to act on new programs.

He believes Holiday’s steadiness was just what the community needed during the Act 46 merger process.

“It’s hard to not get caught up in the emotions and conflicts going on all around us,” he said.

Holiday was never swayed by the Act 46 transition, Paciulli said, and she also ensured that teachers and administrators wouldn’t get caught up in the issue.

Equity, leadership, and Act 46

Holiday hopes the district’s work around social justice and equity — which was started by Stahley and which continued under her leadership — will continue.

The district is contracting with the Vermont Partnership for Fairness and Diversity to update its recruiting practices to attract candidates from more diverse backgrounds.

Specifically, the district hopes to attract more candidates of color so that the school system will reflect the increasingly diverse demographics of the students attending the Windham Southeast schools.

“So that our students are seeing themselves in their teachers,” she said.

She hopes the next superintendent will support school-leadership teams as another way to focus on helping students develop social competencies.

“Because we know when kids have the ability to self regulate, to understand what it means to be an active bystander, that they are more able to contribute to their school in a leadership role,” she said.

A school leadership team varies at each school. The volunteer position looks at the results of the yearly school satisfaction survey.

Led by either a teacher or a counselor, the team might do community service projects. One school’s team noticed that some students had marked on their respective satisfaction surveys that they felt left out during recess.

As a result, the team created a “buddy bench” on the playground. According to Holiday, if kids want someone to play with or are feel alone, they sit on the buddy bench. This signals other kids it’s their responsibility to include this student in their play.

“It’s a chance for students to take on a leadership role within the school,” she said.

Looking ahead with Act 46

While the initial Act 46 merger process is complete, Holiday said the new Windham Southeast School District still has work to do.

She feels the board members are still learning to work together. As the new board conducts policy work and builds a new budget, she believes the schools have strong leadership, so the transition should have no impact on the classrooms.

She thinks that because the schools worked well together prior to the Act 46 merger, little change has been needed subsequent to the reforms. The biggest challenge she sees is at the community level as community members learn to think more holistically about their local school system. The votes of voters in newly merged districts now affect the multiple schools in the merged district, not just one town’s facilities.

“As communities realize that merging doesn’t mean that they lose their small school or lose the personality of their school, then people will understand that we’re all in this together,” she said.

In response to the news floating around that the state is considering creating one statewide school district, Holiday said she can’t see that happening.

“I would want the state to know that what we need in Brattleboro town is not what we need in Dummerston, and what we need in Dummerston is not what we need in Vernon,” she said.

Should any such plans come to fruition, state officials “would somehow need to make some provision” for the uniqueness of each school and its community.

“Cookie-cutter doesn’t work,” she said.

Moving on

For now, Holiday said, her plan is “to not have a plan.”

Holiday wants the freedom to spend more time with her three kids, two of whom live far away. She is also considering some volunteer opportunities.

A hiring committee will scout and interview Holiday’s potential replacements. So far, according to Holiday, the committee has gathered feedback from district staff about what they want in their next superintendent. Next, the committee with begin recruiting candidates.

Over the next six months, Holiday will complete building the next fiscal year’s budget, her final one. She will also complete the foundation for the changes the district will need to make to comply with Act 173, a state law enacted in 2018 which will change how the state funds special education.

Staring in January, Holiday will work with school leaders to develop a plan for transitioning to the new funding structure and to put in place any essential professional development.

Holiday feels unsure about how much involvement she will have with her successor, and the state doesn’t supply mentors for superintendents. Fortunately, in Holiday’s opinion, the Windham and Windsor regions’ superintendents meet monthly and support one another.

And, she added, she will be only a phone call away.

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Originally published in The Commons issue #542 (Wednesday, January 1, 2020). This story appeared on page A1.

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