Kenneth Cheeseman, Head of School, St. David’s School

In an interview with Invest:, Kenneth Cheeseman, head of school for St. David’s School, reflected on his first year leading the institution, the enduring importance of mission-driven education, and how the school is preparing students to lead in a rapidly changing world. “The future really belongs to those students who combine technical competence with moral clarity, creativity, leadership, communication, and wisdom,” Cheeseman said.

What changes over the past year have had the greatest impact on St. David’s School and the families and students you serve?

This is the end of year one for me as head of school, and I have become more convinced that St. David’s has one of the strongest missions and healthiest cultures of any school. Our mission is to prepare young men and women for college and life by challenging them to excel in Christian faith, virtue, and knowledge. In an increasingly complicated world, that mission gives our students something timeless on which to build their lives.

The board of trustees and I began the year with the objective of listening, learning the culture, and understanding where we need to focus. Looking back, the greatest impact has been building relationships. Schools are built on trust, and this year has been about listening to parents, students, faculty, alumni, trustees, and community leaders while creating greater alignment around who we are and where we are going.

We have strengthened our leadership structure, launched an Academic Advisory Council, begun developing a long-range plan informed by our community, and continued investing in academics, athletics, and the arts while improving communication across the school. Throughout it all, we have remained committed to ensuring every student is known, loved, challenged, and encouraged to flourish.

What makes a school’s mission especially important when families are comparing education options today?

I believe a school’s mission has become more important, not less. Families have more choices than ever, and they are not simply looking for a strong academic program. They are asking who will know their child well enough to help him or her become the person they hope they will become.

Each school’s mission answers that question differently. At St. David’s, we believe education is about the whole person. Academic excellence matters tremendously. Character matters equally to us. Faith gives meaning to both. Our mission has endured because it speaks to enduring human needs.

If I were making these decisions again as a parent, I would want to know who could truly partner with my wife and me in our children’s education and help achieve the outcomes we want for them.

We also see that partnership reflected in conversations among families. As research continues to highlight the effects of phones and social media on young people, many parents are intentionally supporting one another in delaying smartphone and social media use. Those shared values strengthen the partnership between school and home.

How does St. David’s prepare students for college, career, and daily life?

Leadership is one of the clearest examples. We talk about leadership, but we also want students to experience it. Because our student-teacher ratio is 8-to-1, teachers know students well enough to give them meaningful opportunities to lead in the classroom, through the arts, and in athletics.

I often say we are not just preparing students to thrive and flourish. We are preparing students to lead. Leadership develops through opportunities to succeed, fail, reflect, and grow. Those conversations happen every day because students learn just as much from challenges as they do from success.

When I met with our seniors for the first time, I told them my expectation as head of school was that they would lead. They were not called to sit back and watch their culture. They were called to influence it.

How is St. David’s approaching artificial intelligence?

AI is an important conversation in education. Some people would rather avoid it, but I do not believe that is the right answer. We are going to engage AI thoughtfully. AI provides extraordinary access to information, but it cannot cultivate wisdom, develop courage, teach integrity, or replace discernment. The future really belongs to those students who combine technical competence with moral clarity, creativity, leadership, communication, and wisdom.

That means helping students understand when AI is an appropriate tool and when relying on it causes them to miss an important learning opportunity. One assignment may allow structured use of AI, while another may require students to complete their work independently so they can compare the different learning experiences.

Our Academic Advisory Council, which includes leaders from colleges and universities across the country, also helps us understand how higher education is adapting to AI. Those conversations have become much more sophisticated over the past year, reinforcing that this technology will continue evolving. Education must evolve with it.

What role do arts and athletics play in developing students?

We believe our calling is to educate the whole person. Students come to us with academic, artistic, athletic, and personal gifts, so we have to provide opportunities that help them develop each of those dimensions.

The arts are an important part of that mission. Whether through visual or performing arts, students develop confidence, character, and creativity in ways that cannot always be replicated in an academic classroom. Athletics provides similar opportunities. Competition teaches resilience, teamwork, leadership, and discipline through experiences that are unique to the playing field.

We are equally committed to academics, arts, and athletics, but just as important is the community that surrounds them. Whether it is a sold-out theater production or a packed athletic event, those experiences bring families together and celebrate students’ growth. Parents are looking for partners who can help develop the whole child, and that requires all three.

What are your top priorities for St. David’s School over the next three to five years?

The priority is strengthening our already outstanding academic program, including taking a deep look at STEAM. While we want to remain rooted in timeless values, we also need to look 20 years down the road and ask what we should be doing today to prepare students to thrive, flourish, and lead in their generation.

Second is continuing to recruit and retain exceptional, mission-focused faculty. With teacher shortages affecting schools across the country, we are intentionally building relationships with colleges and universities that can help us identify educators who embrace our mission and have the expertise to serve our students well.

Third is investing strategically in facilities and programs that support teaching, learning, and student flourishing while remaining responsible stewards of our resources. We want to provide what our students need without getting caught in a facilities arms race.

Fourth is deepening our partnerships with families. Education at St. David’s is a partnership built on authentic communication and shared commitment. Those relationships are also essential as prospective families evaluate the experiences of current parents.

Finally, we want every graduate to leave not only prepared for college but prepared to lead lives of wisdom, service, and faith. Ultimately, the success of our school is reflected in the lives our graduates go on to lead.

Is there anything else you would like to add?

The Triangle does not simply need more educated people. It needs more wise people. It needs leaders of competence and character.

At St. David’s, we believe those qualities are cultivated together in classrooms, on athletic fields, on stages, in chapels, through service to others, and within relationships. We seek to graduate young men and young women who love God, pursue excellence, serve others, and lead with integrity. Those graduates will not only strengthen our school; they will strengthen Raleigh and the communities they will one day serve.

I told our graduating seniors that the call on their lives is to reflect those values and lead here in the Triangle, in North Carolina, and wherever life takes them. That is the work we are committed to every day.