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A head of school and his son discuss AI in the classroom

In the age of artificial intelligence (AI), students are experimenting with new tools—from chatbots that help with writing to tools that generate study guides—as part of their everyday learning. But where’s the line between learning smarter and letting technology do the work? Educators are asking tough questions about academic honesty, creativity, and what it really means to learn. While some schools are embracing AI capabilities, others are banning it outright or trying to walk some middle line. In this edited exchange, Tom Flemma, head of school at North Shore Country Day School (IL), and his son, Max—a senior at the school and a savvy AI user—discuss how AI is changing the way students think about schoolwork.

Click here to read the full article featured in the National Association of Independent Schools Winter 2026 magazine.