This chapter highlights the views of Ms. Bella, a Canadian principal, and Ms. Lan, a Chinese principal, on generalist and specialist teaching models. Ms. Bella emphasized inquiry-based learning, the importance of collaboration, and addressing the stigma of “not being good at math.” She saw generalist teachers needing stronger content knowledge support, especially for the subject of mathematics. Ms. Lan stressed achieving teaching goals, valuing specialist expertise, and finding balance between structure and flexibility. Together, their perspectives reveal systemic tensions and complementary strengths, illustrating how leadership shapes teacher development and reciprocal learning across cultural contexts.