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This AERA 2022 Conference presentation reports on qualitative multi-site participatory research exploring the cultivation of leadership informed by critical pedagogy in two Taiwan classrooms, an experimental intergenerational learning pre-school in Taipei City and an experimental EFL theme-content based class focused on leadership development for junior high school students in Taoyuan City. Implications suggest leadership operates indirectly to promote student well-being by supporting and enhancing conditions for teaching and learning. The cultivation of leadership in classroom curricula has potential to empower all participants (students and adults) as a vehicle for self-awareness, that enhances connections with others, and ultimately enriches communities. Overarching implications offer innovative lesson design and recommendations for policy provisions towards the cultivation of leadership in the Taiwan case.