Climate change, extreme events, and related disasters pose significant challenges not only for the poorest and most vulnerable populations, but also for leaders in disaster and emergency management. Effective leadership entails preparing for and responding to increasing intensities and frequencies of extreme natural hazard events while managing and justifying suffering and loss that communities and individuals experience in case of failed protection. Insight is provided into this double challenge and how it is compounded by the concomitant ways modern societies engage with risk and construct vulnerability and resilience. A conceptual framework is used to show how the rise of modernity, today's risk society, neoliberalism, and governmentality as found in many western democracies, converge to constrain disaster leadership and management, illustrating how interpretations of responsibility and potential loss and suffering have shifted from organizations to individual actors, exacerbating the leadership dilemma in managing hazard-driven crises. This includes ways that neoliberal governmentality warp understandings of vulnerability and resilience by understating one and overstating the other. Through a heuristic, we explain mounting leadership challenges with increasing levels of disaster intensity and consequence, drawing upon natural hazard examples from Australia.