Organizational ambidexterity is positively associated with firm performance. Yet, it is difficult for CEOs to implement ambidextrous strategies as the radical and incremental innovations that underlie ambidexterity are seemingly incongruous. As such, an important task for both scholars and practitioners involves discerning which factors influence organizational ambidexterity. Building on incongruity theory, we address this puzzle by focusing on CEO affiliative humor, establishing its link with ambidexterity, and further developing and testing theory related to boundary conditions. Through videometric analysis of executive interviews, textual analysis of quarterly earnings calls, and a series of supplemental tests, we offer robust evidence for our study's key relationships. Our study thus makes several contributions, including shedding light on a new pathway—CEO affiliative humor—through which firms can carry out and manage the radical and incremental innovations that underlie ambidexterity, as well by highlighting the complementary role of the CEO-director interface in this regard.