Pawling Central School District

National Principals' Month

We are thrilled for the chance to highlight our Pawling principals in honor of National Principals' Month. Though these three dedicated professionals don’t often step out into the spotlight, each of their stories is unique and compelling – and it is our privilege to share them.

Michelle Rivas: Pawling Elementary School

Michelle Rivas might be new to her position as interim principal at Pawling Elementary School, but she is no stranger to Pawling Central School District. Acting as assistant principal for both the elementary and middle schools since 2011, she brought plenty of memories with her to these first few months in her new role.

“I remember feeling so relaxed during my interview all those years ago,” she mused. “I loved the character and atmosphere of the elementary school building but especially the welcome that I received from everyone. It stays in my mind always.”

Now in her 12th year at Pawling, Rivas still enjoys warm support from the school community – but from a different perspective. Whereas she moved between the elementary and middle schools from fall 2011 to spring 2021, landing in the middle school exclusively, her present role presents a whole new set of responsibilities and opportunities.

“Though I’m familiar with the elementary school, the perspective as principal is definitely different,” she said. “I’m comfortable with all of the background work but I have a new responsibility in this job – to support the entire elementary school community and serve them as best I can.”

Though Rivas came into the position with plenty of ideas and vision, she wanted to make sure to gather as much information as possible to align her goals with the school’s priorities. She has been meeting with faculty and staff, both individually and in teams, to learn more about what’s working for them, what’s important to them and how she can help.

“It’s still early in the year, and I’m only just beginning to see the things that I need to focus on,” she said. “I might find that my original vision was way off once I learn more about the school. I could be thinking that we need things that the community doesn’t really need. That’s why it’s so important to me to honor the things that work and get a sense of everyone’s mindset.”

“The responses I’m receiving are so positive,” she continued. “This is a hard-working group of thoughtful, professional and passionate individuals who care about the kids. They come to me with ideas for curriculum, professional development and other things that they need to support their craft.”

She also praised Pawling Elementary’s families and PTA for their strong involvement with their students’ academic experience and school events.

“A lot of people don’t realize how important family support is to our students,” said RIvas. “I’ve been seeing more and more that the families really step up for the kids here. I’m so proud to work with a strong PTA, too. They are such a positive force and work so hard to bring us opportunities that we’d never have without them.”

With her enthusiasm, experience and vision, Rivas hopes to continue building these strong relationships to make this year a memorable and successful one – and it sounds like things are off to a great start.

Megan Gleason: Pawling Middle School

Pawling Middle School Principal Megan Gleason laughed as she watched two goats grazing on the building’s front lawn.

“How many schools have you seen with goats hanging out outside?” she said.

After even a brief conversation with Gleason it’s easy to see these seemingly out-of-place creatures as a testament to the diverse opportunities that she advocates for in her role. Part of the agricultural pathways program, working with these goats is just one of the newer offerings extended to Pawling’s middle school students.

“At the middle level it’s all about exposure and making sure we provide something for everyone to grab on to,” she said. “Kids are doing so much identity work at this stage. It’s all about creativity and making sure we provide them with opportunities that are as unique as they are.”

“By the time they’re in high school certain things calcify in their thinking,” she continued. “I am always considering how we can set them up with self-exploratory experiences to guide them down that path, and I think we’ve made a lot of progress in that area.”

When reviewing the school’s offerings, it certainly seems that she’s made strides toward that goal. New interest-based courses focus on civic engagement, social emotional learning, coding and digital literacy and, along with the chance to join an orchestra ensemble, allow students to explore new areas of interest. Seventh graders also enjoy a STEAM lab (science, technology, engineering, art and math) where they continually evolve their thinking as they develop, test and workshop ideas. The school has also introduced a host of extracurricular activities and clubs.

Gleason brought her expertise and vision to Pawling in 2018 after journeying down a path that began with special education and middle school instruction. This eventually led her to seek involvement with building learning environments with educators as an administrator in a number of districts throughout southern New York State. Mother to an eight year old son herself, she mentioned that she enjoys being able to have a parent’s perspective on the world of education as well.

Though Gleason takes pride in her work, she asserts that none of these accomplishments have happened in a silo – and that Pawling’s culture and small size is what makes that possible.

“There is such a commitment from the teachers, staff and district administration at all levels to maintain and grow these programs,” she said. “The equilibrium of having longtime administrators coupled with new faces lets us evolve with the community, and I love that.”

“Our entire district is rare, and I’m honored to be a part of it.”

Helen Callan: Pawling High School

A member of the Pawling community for 25 years, Pawling High School Principal Helen Callan’s connection to the district is both professional and personal. When she moved her family to the district in 1998, she never dreamed she’d be working in the same school that her children attended, much less leading the high school as principal over two decades later.

“When I came in to register my children for Pawling Elementary, I was asked if I’d be interested in subbing,” Callan said. “I ended up becoming a teaching assistant and found that I loved teaching and had a passion for it – so that was the beginning of my story here.”

Callan spent the next few years working on her teaching certification and growing her career in the district, gradually moving from elementary school teacher to dean of both the elementary and middle schools. She landed in her current position in September 2012 with a deliberate approach, working toward gaining a comprehensive picture of the school.

“Like anyone starting a new position I wanted to do a good job, but I didn’t think that meant coming in and changing everything,” she said. “Everyone asked, ‘what are you going to change?’ and I responded, ‘nothing yet!’ I needed to meet the faculty and staff, get to know the students and see why things were happening the way that they were.”

Callan’s investment in the students was deepened by the fact that she had known most of them since they were very young during her time at the elementary school.

“Here’s what has been wonderful,” she said. “I got to know every single person and every single student. I knew kids from back when I was teaching and in my role as dean of students. I still remember this year’s seniors as kindergarteners.”

Now in her 13th year as high school principal, Callan has familiarized herself with the school community and then some. She has been able to streamline processes and provide a host of new course offerings to Pawling’s most experienced students as well as create a building culture that ushers them into their young adult lives prepared for their chosen direction.

“The high school serves as the dock where the ships go off into the ocean, but it’s important to recognize that behind each student is an entire team of educators and support staff that have worked tirelessly to get them to this point since their first day of kindergarten,” she said.

“There is something comforting in that we as a school are able to get to know each other and our students so well throughout the years,” she continued. “I’m grateful for that every day.”