Public policy can play an important role in steering the large-scale diffusion of teleworking. Various communities around the world are experimenting with innovative solutions. In Italy, the Autonomous Province of Trento has plans to design a comprehensive plan for teleworking as a way to foster local economic and social development. Opportunities and challenges for a smooth transition to an ever more hybrid work environment are explored in view of a number of societal objectives, including an improvement in living standards, territorial cohesion and competitiveness. The paper identifies six policy areas for recommendations, reflecting the conditions needed to achieve these objectives.