Leaders across sectors and organizations currently face large, urgent, and complex adaptive challenges demanding new ways of leading. This chapter examines the practices of the Rt Hon. Jacinda Ardern, Prime Minister of New Zealand in complex crises, illustrating the role of compassion and clarity in effective leadership. A qualitative analysis of policy and media data reveals several key features that exemplify Ardern’s leadership in the 2019 major terrorist attack on mosques in New Zealand and the global COVID-19 pandemic. These include acknowledging and navigating complexity, mobilizing others, communicating with clarity about evidence-informed decision-making amidst uncertainty, and leading from a stance of empathy, compassion, and kindness to develop relational trust. This chapter concludes by synthesizing how effective practices identified through the analysis of Ardern’s leadership might be developed in and across other contexts and cultures.