St. James Academy Head Charlotte Riggs Leads with Empathy and Compassion

Share the News

St. James Academy
Ms. Riggs welcomes students on the first day of school with her fairy wings.

Monkton, Md. – For her first day of school as St. James Academy’s new head of school, Charlotte Riggs made a unique – and strategic – accessory choice. She donned pastel-colored wings, which she wore to greet the 270 PreKindergarten through 8th-grade boys and girls, their parents, and the faculty and staff at St. James Academy (SJA), an independent school in Monkton.

Riggs is no stranger to first-day-of-school jitters. She’s logged 39 first days of school beginning with her own independent school education and throughout her long career in coaching, teaching, and middle school administration.

But in her first role as a head of school, the wings were a chance to lead with empathy right out of the gate.

“I wanted to create a moment for our students on the first day that would be a moment for every student, whether in our new PreKindergarten program or starting 6th grade,” explains Riggs, who began her SJA head of school tenure last July. “If they were nervous and had butterflies, I told them that I had them, too, just look at my wings.”

The youngest students still ask her where her wings are (in her office, waiting for the right moment), and probably wondered where they were on October 10 for the all-school celebration for Riggs’ official installation as head of school. But Riggs hardly needs her conversation-starting costume: her reason for wearing them -– to nurture connection -– is part of who she is. Her philosophy and welcoming, grounded demeanor complement the Academy’s mission of educating the whole family. “One of the things that drew me to St. James is its commitment and dedication to the community,” she says. “It’s an openness and understanding about what is best for each child.”

St. James Academy
Mrs. Kirsten Prettyman Adams, Head of School at St. Stephen’s and St. Agnes School, introduces Ms. Riggs at her Installation service on October 10, 2018.

The St. James faculty and staff accomplish this, Riggs explains, through clear communication between teachers and parents and a robust parent education series that helps parents learn more about their child’s stages of development. On Tuesday, December 4, Leonard Sax, M.D., Ph.D., psychologist and New York Times best-selling author, will speak at St. James Academy. At 9 a.m. he will discuss “Why Gender Matters” and at 7 p.m. he will discuss “Evidence-Based Parenting.” The free, adults-only events are open to the public. (To register, go to

Throughout the year, St. James parents attend panels led by SJA’s child psychologist, Lucie Pentz, Psy.D. and SJA faculty. The panels cater to a specific age but are open to all SJA parents and the community to get the long view. “Our program provides information and gives opportunities for parents to come together and share insight and gain another perspective,” says Pentz of what she calls “starting conversations.” After any outside speaker, SJA faculty and staff, she says, continue to encourage discussions on the topic. In fact, Sax’s recent book was an SJA faculty/staff summer read with subsequent faculty-led presentations about it, part of the school’s professional development program.

“For parents, the tricky piece is how to find the moments to be present and listen to your children,” adds Riggs, who grew up in Owings Mills as one of three children. “In the classroom, we need to understand what is important to each individual child. When I was an art teacher, I found out what [my students’] passions were. Our teachers understand this age group really well and what it takes to keep them curious, help them explore, and to get to know themselves. When our families know that we are encouraging their child at school, they can encourage safe, appropriate risks as well. It only pays off for the child.”

For Jessie Sheckells, an alumnus and the SJA Patrons Association president, the school’s philosophy matches how she and husband Fred are raising their son, who is in 6th grade. “I have a very empathetic young man, and I attribute that to SJA,” Sheckells says. “Parenting is hard, and it changes year to year. The Academy is helping us make the right decisions by our families.”

She values Riggs’ balance of gentleness and the accountability needed for preschool through middle school children and her vision: “Charlotte has worn a lot of hats and is ahead of the curve in her thinking.” (And, yes, her son thinks Riggs and the wings are cool.)

Riggs’ years in the classroom and as a school administrator -– she began her career in 1998 as head coach of Northern California’s Acalanes Girls Lacrosse Club before receiving her M.A.T. in Visual Arts from Philadelphia’s University of the Arts -– gave her an eye for the teachable moment. She first set her sights on a teaching career much earlier, though. “I recall asking my elementary teacher how she got her job,” says Riggs with a laugh. “I thought the interview was drawing a tree.”

Her path to administration began with an encouraging push at the Woodlynde School in Strafford, Pennsylvania, where Riggs was teaching middle and high school art. A colleague suggested she apply for an administrative position in the school. “From there, I became interested in the bigger vision. Questions of ‘Where are we going?’ and ‘How do we get there?’ drive me,” says Riggs, who was the director of Middle School for St. Stephen’s and St. Agnes School in Alexandria, Virginia, before being selected for her first head of school position at SJA.

St. James Academy students
Student acolytes serve at Ms. Riggs’ Installation service on October 10, 2018.

She cites SJA’s faith-based curriculum as an Episcopal school and its All-School Chapel program for inculcating leadership and character-building opportunities for all students. Riggs has joined SJA at an auspicious time: the school’s parish, St. James Episcopal Church in Monkton, welcomed a new rector this fall, The Reverend Joe Cochran. He, too, is taking on top leadership duties for the first time in his career.

Riggs is thrilled to embrace each moment, the big and strategic ones and the every day, quieter ones. “We’re focused on the work we need to do now that students and families will benefit from in the future,” she says. “It’s all exciting conversations about how St. James Academy is preparing our students for the world, not the next step.” She’s quick to point out, though, that the next step – high school – is important. SJA’s high school decision-making process centers on self-awareness and reflection, Riggs explains. “[Our students] take what they’ve learned here -– socially, emotionally, academically -– and that galvanizes them in their development and decision-making.” Qualities, Riggs knows, that are essential for taking flight.

Share the News