Q: First of all, welcome back to Pasadena! Which school were you at previously, and what position did you hold there? Can you tell us a bit about your background in education and the path that led to your current role?
A: Thank you so much, I am excited to be back in Pasadena and honored to serve as the principal of Chesapeake High School. Most recently, I served as an Assistant Principal at Old Mill High School during the 2024-2025 school year. Before that, I spent eight wonderful years as an Assistant Principal here at Chesapeake High, so returning in this new role truly feels like coming home.
My career in education began as a Special Educator working in Kennedy Krieger Institute’s High School program, where I developed a strong foundation in supporting diverse learners. I later transitioned into school leadership, driven by a passion for creating inclusive and student-centered learning environments. In July of 2016, I joined Anne Arundel County Public Schools to serve the community in which I live. It is incredibly meaningful to now lead a school in the same county I call home, and I look forward to partnering with students, families, and the greater Pasadena community to support the continued success of Chesapeake High School.
Q: Are you originally from Anne Arundel County? Where did you grow up?
A: I am originally from New York and moved to Maryland in 2002 to pursue my master’s degree in education. After graduation, I chose to stay because I truly fell in love with the area and the strong sense of community. Maryland has been home ever since.
Q: What inspired you to pursue a career in educational leadership?
A: There were several key moments early in my career that inspired me to pursue educational leadership. When I began working at the Kennedy Krieger Institute, I started in an entry-level support position and worked my way up through various roles until I left in 2016. That experience helped me understand the value of growth, mentorship, and dedication. What truly motivated me to step into leadership was my belief in servant leadership and my desire to support both teachers and students in becoming the best versions of themselves. I am committed to doing whatever it takes to remove barriers and create the conditions for their success.
Q: What excites you most about working at Chesapeake High School?
A: What excites me most is returning home to the school community I love. Chesapeake has the most incredible community of students, teachers, families, and partners I have ever experienced. The strong relationships, dedicated educators, and amazing students create a truly special environment. I feel honored to serve a school where the sense of pride, connection, and commitment to student success is so deeply rooted.
Q: What is your vision for the future of Chesapeake High School, and how do you plan to achieve it?
A: My vision for Chesapeake High School is to advance both academic and social growth while enhancing communication to deepen community engagement. Building on Chesapeake’s proud tradition of success, I aim to strengthen high-performing academics, competitive athletics, vibrant programs in music, drama, robotics, and more. Above all, I want every student to feel valued and every interaction to be grounded in respect.
I am committed to fostering a culture where students are engaged, parents feel welcomed and heard, and staff are fully supported. I greatly respect the progress made under Mr. Yore’s leadership and look forward to continuing that work to elevate our school to new levels of excellence.
Q: As a high school principal, how do you measure your success? What characteristics, in your opinion, make a truly “great” school leader?
A: I measure success by whether individuals have grown into better versions of themselves from the moment they enter our school to the moment they leave, no matter how long they are with us. For students, that means academic growth, personal development, and a stronger sense of purpose. For staff, it means continuous improvement, professional fulfillment, and a sense of shared accomplishment.
In my opinion, a truly great school leader is student-centered and grounded in the principles of servant leadership. They prioritize the needs of students, teachers, and the broader school community above their own. They foster a culture of trust, collaboration, and empowerment by actively listening, supporting professional growth, and removing barriers to success. Great leaders model empathy, lead by example, and work alongside staff to create a shared vision rooted in academic excellence, the holistic development of every learner, and community involvement. This kind of leadership builds strong relationships and a positive school climate where everyone feels valued, supported, and motivated to thrive.
Q: Can you share an example of a time when you successfully implemented change at a school?
A: Yes, I have led several successful changes focused on improving systems within schools. On a smaller scale, I have worked to streamline expectations and improve organizational structures for teachers, helping to create more clarity and consistency across classrooms. On a larger scale, I have led significant initiatives in workforce development, including training for teachers, guiding students through career exploration and pathways, and developing strategic systems to support majors and post-secondary opportunities that lead to gainful employment.
Throughout my time as an administrator, I have consistently focused on identifying opportunities for improvement, removing barriers, and designing systems that increase efficiency and impact. My goal in every initiative is to maximize success for both students and staff while creating sustainable, student-centered change.
Q: In what ways will you engage with parents and the local community to build a strong support network for the school?
A: I believe that strong communication and active participation are essential to building a successful support network between the school, parents, and the local community. There is no success without the partnership of our families and community members. I need their voices and involvement.
I will invite parents to engage through volunteering, chaperoning, attending extracurricular meetings, and participating in events such as Back to School Night. I also plan to hold regular opportunities for dialogue, starting with my first Coffee with the Principal on July 1. At that event, I want to hear from community members about their experiences, needs, concerns, and suggestions.
Since attending events is not always possible for every family, I will also send out surveys and provide multiple ways to communicate so everyone can share their feedback in a way that works best for them. My goal is to create open, two-way communication and then use the information gathered to address concerns, improve outcomes, and build a stronger school community together.
Q: What’s one interesting fact about yourself that people may not know?
A: One interesting fact about me is that I was an athlete. I was a gymnast in secondary school and played collegiate rugby. The rugby part usually surprises people, and I think it highlights my determination and strong work ethic.
Q: When you’re not busy with school-related work, what kind of hobbies and activities do you take part in?
A: I really enjoy photography, especially capturing scenic views. Whenever I have the chance to spend time outdoors in nature, I truly appreciate it. There is something very grounding and inspiring about recognizing a world much larger than myself.
Q: What’s your favorite vacation destination?
A: My favorite vacation destinations are always places near the water. Ocean City, Maryland, is one of my favorite spots, but honestly, any beach, lake, or ocean is an easy favorite for me.
Q: What’s your favorite book you’ve read in your lifetime?
A: One of my favorite books is The 7 Habits of Highly Effective People by Stephen R. Covey. It has had a lasting impact on how I approach leadership and my own personal growth.
Q: If there’s one message you could communicate to Chesapeake students and parents ahead of the 2025-2026 school year, what would it be?
A: The 2025-2026 school year at Chesapeake High School is going to be an incredible one! My administrative team and I are hard at work this summer preparing to welcome our students and families with fresh energy, renewed purpose, and a clear focus on excellence. Whether you are returning or joining us for the first time, we cannot wait to see you this fall.
This year, we are committed to creating a school experience where every student feels seen, supported, and empowered to thrive. That includes success in the classroom, on the stage, on the field, and within the community. We are building something special at Chesapeake, and we are so excited for you to be a part of it.
Q: Finally, what’s the best way for parents to get in contact with you?
A: Parents can reach out to me in whatever way is most convenient for them. They can email me, share feedback through surveys I send out, visit me during school events, call the office, or arrange an in-person meeting. I look forward to connecting with families and working together to support our students.
Principal Shanna Cahoon will host Coffee With The Principal, a casual opportunity to connect, share ideas and discuss the year ahead with parents and the local community, on Tuesday, July 1, 2025 at 8:00am in the Chesapeake High School cafeteria. Whether you’re a longtime member of the Chesapeake community or new to the school, Cahoon encourages anyone interested to attend.
