By Crawford Craig

There’s a familiar face in the halls of Collegiate this year—only now she’s on the teaching side of the classroom. 

Cougar alumna Abby Fleming (‘21) recently returned to the familiar community she loves, this time as a Middle School Spanish Teaching Fellow. With her enthusiasm for language learning and approachable presence, Fleming is eager to deepen her teaching experience and enjoy every moment with her new Spanish students. 

Fleming at her Virginia Tech graduation.

After graduating from Collegiate in 2021, Fleming attended Virginia Tech, where she earned a B.A. in Spanish with a minor in International Studies. While new to teaching this year, her rich academic background and eagerness to learn made her the perfect candidate for Collegiate’s Fellows Program, now in its second year. Last year’s Teaching Fellows included Upper School history teacher Lat Peak, Cub football coach and Middle School math teacher KJ Rodgers (‘19), and Upper School science teacher Maisie Harper. The latter two have stayed in the program through this year as well. 

Fleming recalls her passion for Spanish starting right here at Collegiate during her first year as a Cougar in 9th Grade, with Upper School Spanish teacher Hannah Curley. Fleming recalled, “Señorita Curley made it easy for me to want to learn Spanish in a way that I had never felt about another school subject before.” Subsequent courses with Upper School Spanish teachers Elsie Bustamante and Esperanza Soria-Nieto deepened her appreciation for both the cultures and traditions of Spanish-speaking countries. Those teachers, Fleming shared, were early inspirations for her path towards a career in education.

Fleming grew up in Richmond and is one of four children, with three brothers—two older and one younger. She is also the proud owner of her affectionate pit bull named Whiskers. When she’s not busy teaching, writing lesson plans, or volunteering after school, you will find Fleming taking a local yoga class a few times a week or cozying up with an enjoyable book. Her favorite genres are literary fiction and thrillers, and she is “always open to any book recommendations.”

Collegiate’s Fellows Program, led by Dr. Leah Angell, is a special endeavor created to attract promising new faculty to our school, fostering not only the academic rigor of Collegiate but also the community’s enduring values. According to Collegiate’s website: “The purpose of the Fellows’ Program is to provide aspiring educators with the mentorship, classroom experience, and pedagogical background necessary to become a lead classroom teacher. In keeping with three of the School’s core values – love of learning, excellence, and community – the Program strives to foster and support each fellow’s lifelong journey in the field of education.” 

Fleming’s application to the Fellows Program included submitting her resumé, a Spanish writing sample, and essays expressing her interest in the job. The next steps included Zoom interviews with faculty on the hiring committee, followed by an invitation for a day of meetings on campus with the Spanish faculty, administrators, and Head of School Jeff Mancabelli, and a teaching demonstration to share her teaching skills and interactions with the students. After enjoying her application process, Fleming was excited to hear back from Dr. Angell that she had been offered the Middle School position for the 2025-2026 school year. Getting the exciting news and returning to Collegiate felt natural to Fleming. “The sense of community here is just so strong, and it’s not something that you can find at any school. I knew that, upon returning to Collegiate, I would be supported, heard, and taken care of as a teacher.”

Now settled into her new Collegiate routine, Fleming’s school days are full and varied. Upon arriving at school, she helps out with one 9th Grade and two 7th Grade Spanish classes. She is also assigned to a 7th Grade girls Advisory and two study halls. After her classroom obligations, she has several meetings throughout the week. Specifically, she meets weekly with Dr. Angell and her Fellows Program cohort. She also has time carved out for one-on-one meetings with her mentor teacher, Middle School Spanish teacher Nicole Weber (‘10). Eager to learn as much as she can about teaching this year, Fleming spends additional time observing other Spanish classrooms in the Middle and Upper Schools and has plans to branch out to other subject areas to experience those teaching styles, too. On Tuesday, Wednesday, and Thursday afternoons, she heads to Quioccasin Middle School to tutor for the STAR (Strengthening Teens Academically and Recreationally) program, sponsored by The Tuckahoe Family YMCA, where she works with Juniors and Seniors tutoring immigrant and refugee students.

Fleming’s work with her students at both Collegiate and Quioccasin—along with the guidance of her mentors—is quickly shaping her teaching philosophy. Her approach focuses on developing strong relationships and expressing her warm personality with students. She believes that when students feel connected with their teachers, they are more likely to engage in class on a more meaningful level. Fleming also employs a well-rounded approach in her Spanish classes, offering students rich and balanced opportunities for “reading, writing, listening, and speaking as much as possible, so that they’re not only learning how to read Spanish, they’re learning how to use it in a broader context.” With a keen eye for how her students are performing and experiencing the demands of the curriculum, Fleming is aware that there are times when students struggle or feel uncertain. While she is still figuring out the best approach to help these students, she’s found that students respond best to positive reinforcement. That means Fleming carefully tracks student progress and offers praise when things are going well, with the hope that when things are difficult, students have developed a sense of perseverance to work through the challenges. 

Fleming noted that one of the major transitions from student to teacher is classroom management, which pushes her out of her comfort zone. Middle School, she explained, has an entirely different energy than Upper School. The students have more difficulty settling down and focusing, which has been an adjustment for Fleming. Having previously worked with students with autism in a one-on-one setting at The Faison Center, shifting to managing a class of twenty students has created a learning curve. But Fleming is reminded that Collegiate is a supportive community, and she’s not alone on her teaching journey. “Dr. Angell and my mentor teacher, Señora Weber, have given me so much support in this regard. Señora Weber has shown me what has worked for her and given me a safe space to figure out what might work for me. Dr. Angell has provided me with different articles and readings about classroom management that have helped me tremendously.” Fleming admits that one thing that has surprised her now that she’s on the teacher’s side of the desk is the amount of behind-the-scenes planning and preparation that teachers pour into their classes. She came back to Collegiate ready and eager for the challenge of teaching, and now she realizes the full extent of all the hard work and time that goes into classroom management, grading, lesson planning, and writing comments.

Taking some time to reflect on what makes Collegiate so special to Fleming, she recalled that one of her favorite Cougar memories occurred during her Senior year in the Upper School. Sadly, her graduating class of 2021 never enjoyed the tradition of their Senior Prom because of the impacts of COVID-19. Aiming to create memories for the students, Upper School administrators and staff organized a special Cougar Casino night, instead of a traditional dance. After a fancy dinner together on the front lawn, the students all gathered in the Academic Commons for games, bingo, and a magician. “I remember having so much fun with my classmates, even though it was quite an unusual event.”

Finally, when asked to reflect on what piece of advice she’d give to her Middle School self, Fleming answered with the same warm demeanor her students and colleagues know so well: “Do not give up when things get hard, stay curious, and keep challenging yourself to be better.” 

All photos courtesy of Abby Fleming.