Drawing on a survey of 25 mayors of municipalities belonging to the Metropolitan City of Milan, Italy this paper presents an investigation into the main problems they faced during Phase 1 (lockdown) and Phase 2 (post-lockdown, pre-vaccine); the leadership actions they implemented in Phases 1 and 2; and the leadership actions they would prioritize in case of a new emergency. The results contribute to the building of knowledge on local governance and leadership models – specifically regarding conditions of emergency. Four key issues emerged: (i) the importance of adaptive leadership and of anticipatory governance frameworks aimed at providing direction in situations of emergency (e.g. what to do in case of scarce mask availability and/or of l...