This chapter explores how exemplary Thai school principals cultivate effective teacher collaboration within Thailand’s high-power-distance, collectivist context. Teacher collaboration is widely regarded as a key driver of school improvement. However, in hierarchical settings, it often faces unique challenges. This qualitative, multicase study examines three schools, each led by a nationally recognized principal, to gain in-depth insights into leadership strategies that foster sustained collaboration. Findings reveal four key strategies: fostering a supportive and open culture with camaraderie, employing structured alignment with a career focus, building bridges beyond school, and valuing teacher voice and agency. Principals successfully balanced national reform goals with cultural norms by fostering a “Kan Eng” (friendliness) environment, promoting mutual respect, and utilizing clear communication. They integrated Professional Learning Communities (PLCs) and Performance Agreements (PAs) into a strategic, career-focused structure, reinforcing the collectivist value that success is shared. Furthermore, principals empowered teachers by seeking their input and delegating leadership roles, thereby building ownership. The study suggests that culturally responsive leadership, which strategically leverages values like Kreng Jai (consideration) and Nam Jai (generosity), is crucial for instilling teacher collaboration and professional learning. These insights offer a globally relevant model for school leaders seeking to foster effective collaborative cultures in diverse and hierarchical educational settings.