Sheffield — Charles Miller has a penchant for footwear. Seriously. He wrote a thesis on sneaker consumerism, which, after immediately noticing my own footwear — a pair of Allbirds wool runners, charcoal grey — made perfect sense. Miller, clad in a classic pair of L.L. Bean hand sewn Blucher mocs, is the newish elementary principal for the Southern Berkshire Regional School District where he sits at the helm of Undermountain Elementary, New Marlborough Central and the South Egremont School.
In the first four months on the job, suffice it to say Miller has hit the ground running, and he is paying close attention to detail. Everywhere. Miller, who grew up as one of five siblings, counts family as an integral part of his life. His time spent living and working in New York City and Boston made him realize he didn’t want to be in a city, but rather in an area that boasted community, access to the outdoors and culture. Which, suffice it to say, means all involved have hit the proverbial jackpot: Miller has landed in the Berkshires, and families in SBRSD are hopeful that his leadership will result in a tenure marked not only by success but also longevity.
Hannah Van Sickle: What is one of your favorite parts of the school day?
Charles Miller: Definitely arrival. From the beginning of this year, one thing I always remember is my own elementary principal—I went to an all boys’ school—who knew the name of every single student coming in each morning. I love seeing the energy at the beginning of the day, especially as you don’t know what’s going to transpire, which can also be exciting. The top of the morning: It’s like a really good part of the day. Ultimately each day is scheduled and then it never ends up that way. I can’t necessarily predict what each day is going to look like beforehand but, being out in the classrooms, I really enjoy observing instruction and then those follow-up meetings with teachers. Take Title I foundations, for instance, a curriculum that is new to me: to have the instructor describe it, for me to do a little bit of homework, but then to go and see what it actually looks like and to see how the kids are responding to it in kindergarten or first grade is a great part of any day—going in and being in the classrooms.

From left: Sen. Adam Hinds, D-Pittsfield; Southern Berkshire Regional School District Superintendent Beth Regulbuto; SBRSD elementary school Principal Charles Miller; and South Egremont School teacher Sarah Cook, at the 243rd birthday of the town of Egremont in August. Photo courtesy Southern Berkshire Regional School District
HVS: What drew you to the Berkshires?
CM: A variety of things. First, I was looking in Massachusetts — my wife and I knew we wanted to be in Massachusetts — and the majority of schools at which I was interviewing were much more local to the Boston area. I was looking in Somerville, Watertown, but not Boston Public Schools because I didn’t want to be in a large school district. I was working at Warren-Prescott (in Charlestown), but I knew that I wanted to be in a smaller district. A lot of districts I was looking at were smaller than 80 elementary schools, more like two or three, so Sheffield and the Southern Berkshire Regional School District fit that model. The reason I knew about the Berkshires is that my folks live in Norfolk, Connecticut. I came out here, I did a tour of the school, I met with students, met with the superintendent, met with the director of student services, and I was really impressed with the teachers and administrators I met. I felt like, “Wow, this could potentially be a forever home.”
HVS: Has there been a particular moment this fall that has embodied the spirit of SBRSD?
CM: One is the school musical. We have rare opportunities when New Marlborough students, South Egremont students and Undermountain students are all doing something together. I spent the summer meeting with everyone from custodians to the superintendent and everyone in between — I tried to sit down and spend 30 to 40 minutes with anyone who was willing to — and I remember band director Courtney English talked about how other schools might have a theater clique, where kids might sometimes be alienated, but that, at Mount Everett and Undermountain, it didn’t feel like that. It’s such a small school that people are all supporting the arts. Seeing the amount of people who came out to support the musical each night — it was a packed house for three performances — and to see how much the kids loved it, enjoyed it and were talking about it afterwards embodied one of the reasons I was really attracted to this district: a community district. People wear so many hats. Another moment would be our character trait assemblies: not because of the content, but due to the amount of effort that teachers and students put into presenting on the character trait. The last one was respect — it was eclectic in terms of what students presented from grade to grade. We also had participants from the high school trip to India who came and did a dance, so there was a lot of buzz — especially in the older grades — how cool that was, which reinforced, again, the fact that we are a collection of schools, not just one school standing alone.
HVS: As fall transitions to winter, where do you see room for growth in the district’s elementary schools?
CM: I have a lot to learn still about the school, about our instruction — not so much about our curriculum but what it actually looks like and how it plays out. I definitely feel I have a good sense of the staff culture, and I’m getting a greater sense every day of student culture. There are things from day one that I’ve seen and observed and heard about that present opportunities for growth, but I’m very slow to prescribe them for a variety of reasons, one being there has been a ton of turnover, and so I really want to be sure I build these improvement efforts with consensus. One thing we are doing at our next faculty meeting — rather than having an improvement plan that I create and implement from the top down and gets prescribed to each classroom — is having a conversation about the academic priorities: Based on the different assessments of performance that I’ve seen, now I want to get teacher input on what they’ve seen. To get a larger school improvement plan, I think it’s really important to build that collectively.
HVS: What is your vision going forward?
CM: The relationship piece is critical. Culture eats strategy for breakfast: If you don’t understand the school culture, you’re not going to be able to change things effectively and in a way that is sustainable. For example, I might disagree with another teacher/administrator about what’s in the best interest of children. We are both going to keep it student-focused but, if that individual does not trust me and where I am coming from, s/he is going to be less willing to try something that I think could potentially work. Having said that, I do obviously have to make decisions that are not always popular — it is not a popularity contest, as anyone in school administration can tell you — at times it’s a thankless job. But what makes it so meaningful and valuable, regardless of whether or not someone likes or dislikes a decision, is seeing student outcomes improve.