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Speaking with the Dwight Deans as a group is an exercise involving one part “great minds think alike” and one part “electric energy.” Their boundless energy is catching, even as they talk about the many, many tasks that they take on in any given day. It’s clear that the energy emanating from them and between them is what sustains such a demanding role — one that touches on literally every facet of the Upper School as they strive to meet the needs of nearly 100 families in each grade, and is performed on top of other duties at Dwight, as the Deans also teach or hold other roles at the school.

Dwight’s Upper School Deans are a unique feature of our School, placed front and center in the lives of students, while also working in a very behind-the-scenes way. Quite the oxymoron, we know. 

“The role is difficult to encapsulate,” says Head of Upper School Eric Dale to whom the Deans report. “In the general sense, they are tasked with the pastoral care of the students in the grade, but the work is so much farther reaching than just that. The Deans are expected to have a good sense of each student's academic standing, social wellbeing, and particular sparks of genius.”

From there, the Deans work to nurture each of those things. And they’ve been quite successful at doing so, as is reflected in the praise of our students.

“I really can't put it into words how much all my Deans have helped me,” says Mariam Diallo ’25. ”All the Deans that I’ve been honored to have are confidantes of sorts for in and out of school obstacles. I appreciate the respect and understanding they have for the students at Dwight.”

“Student support is our number one job.” 

So says Ms. Rubenstein, longtime Grade 9 Dean, who just started her eighth year in the role.

Deans do whatever needs to be done to support students and support parents to support students and support teachers to support students in their day-to-day interactions — speaking with parents, shepherding kids to counselors, teasing out and resolving issues, and working very closely with Mr. Dale, “almost in the capacity of ‘Vice Principal,’” as Mr. Horvath, now in his fifth school year as Grade 10 Dean, describes it.

“But as a Dean,” he continues, “You're not only social, emotional, and behavioral support, you're also very much in the weeds with the Heads of Departments, academic questions, and integrity.”

So, while parents and students should never hesitate to bring issues to the Dean, they help with so much more than that. 

Community Builders, Communicators, and Connectors

Deans set the tone with Community Meetings, making sure that community norms are clear — and can be upheld. 

“During Community Meetings,” says Ryan Franciscovich ’25, “Deans share school-wide updates, celebrate student achievements, and remind us of important deadlines for assignments. They also invite guest speakers, such as college counselors, to provide additional guidance. Deans use this platform to promote values like respect, empathy, and compassion, reinforcing the positive and inclusive culture at our school.”

They also support our faculty and staff, day-to-day, by making sure that everyone is in the loop on student news, but also with sweet gestures like well-timed breakfasts during the busiest periods, and the famed Annual Ciderfest Flannel Best party that happens every Fall.

Deans get to know every single Upper School student and family at Dwight. They challenge students to be their best and truly thrive in the Upper School, socially, emotionally, and academically. And given the Deans' holistic view of each student, they also tend to be the first point of contact for all matters; they are continually liaising with all members of the student, parent, and faculty communities to create a tightly woven web of communication that assures all needs are met… usually even before they become needs.

Grade 12 Dean Bentley Ferraina puts it succinctly, using a basketball analogy: “The Deans act as a point guard for each of our grades.”

Mr. Ferraina was Grade 10 Dean for five years before becoming the Grade 12 Dean this year.

He elaborates: “Almost every conversation with a parent or a student or a teacher that's like, well, who do we ask about this? Then the answer is always, I guess you just ask the Dean. And even if we're not the people who make the decision, we're making sure the parents are talking to the right people or the students are talking to the right people.”

A Solid Team Effort

If it wasn't clear to the reader by now, the Deans are a collective force, working with one another and Mr. Dale in a tight-knit way. 

“We often bounce a lot of things off of each other,” says Mr. Horvath. “‘Hey, am I accurate here? Hey, is this tone okay?’ Because we're interacting with so many different people and so many different personalities.”

Adds Mr. Ferraina: “And we really have to be aligned because the students notice when certain things are being enforced differently or treated differently or addressed differently in Community Time meetings.”

And, of course, information on each student and family gets formally transmitted from year to year, which is extremely helpful to families in transitioning between grade levels. “If Michael has something going on with a tenth-grade student and he wants to know what happened in ninth grade, we will talk a little bit about that,” says Ms. Rubenstein. “And we do that in every grade. We pass that information down.”

One of Many Hats

Which brings us to the newest member of the Dwight Deans team: Paul Vliegen steps into the role of Grade 11 Dean as an active member of the community. Mr. Vliegen has developed strong relationships with his students, whether it be as a Global Politics teacher, as a former advisor of PRISM (the Pride, Raising Awareness, Involvement, Support, and Mentoring Club) as the Model UN advisor, as a chaperone on multiple student trips, or as the former Head of Upper School Individuals and Societies.

“I am looking forward to getting to know each and every student in the eleventh grade,” says Mr. Vliegen, “My favorite part of being an educator is the daily interactions with adolescents — learning about their perspectives on the world, who they are, and who they want to become.”

Mr. Vliegen will continue to teach Global Politics during his tenure as Dean, just as Ms. Rubenstein teaches Grades 6 through 8 Personal and Social Development and remains a fixture on the Rugby pitch as Varsity Head Coach; Mr. Horvath teaches Grade 8 PE; and Mr. Ferraina will work with the Upper School Admissions team and continue his Film Club. Having multiple roles at the School means that our Deans are integrated deeply into the community, continuing to bring in different viewpoints. 

So our Dwight Deans aren’t just sitting in a stuffy office — though when they are, their door is always open. The Deans are here to help, as Mr. Vliegen points out when he was asked why he wanted to be a Dean.

“I am looking forward to helping our students develop the skills and resilience to navigate the world they are growing up in, without losing sight of what ultimately matters most: integrity, kindness, and compassion — to ourselves and others.”

Read more student reflections on the Deans here.

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Thanks to Mr. Cunningham and Ms. Sayers for their service!

At the end of 2023-24, Alex Cunningham stepped down as Grade 12 Dean after a decade at Dwight School and seven years in the role. He’s now Grade 11 Dean for Dwight Global Online (and Blended Students Coordinator for all of Dwight Schools). 

Ellen Sayers stepped down after an incredible 19-year tenure (first as Grade 10 Dean, then as Grade 11 Dean for the last 8 years) to focus more her role as Head of the Visual Arts Department and to make more time for creating community arts events.

When asked what they’ll miss about being Dean the most, both, without hesitation, responded, “The students!”

Head of Upper School Eric Dale is flush with examples of what they brought to the role in their time.

“Ellen helped create the first iteration of the Deans' Council,” said Mr. Dale. ”Ellen should be credited with building in levels of advocacy that did not exist previously, and our students, parents, and teachers are all better supported because of it.”

Of Mr. Cunningham, Mr. Dale said, “He could just as easily help students learn about themselves through self-reflection in TOK as through the physicality of a boxing class. His own adaptability has served our students well, and with this, he has strived to help each graduating class establish their own ethos unique to them, not specific to him.”

Both, though greatly missed in the role of Dean, have left an indelible mark.

 

 

Read This Story and More in Our Most Recent Issue of Dwight Today!