The digital transformation is impacting various aspects of how we live and work. Due to the pervasive effects of the digital revolution on firms and societies, both scholars and practitioners are interested in better understanding the key mechanisms behind the related challenges. This book presents a collection of research papers focusing on the relationships between technologies (e.g. artificial intelligence, social media, and the Internet of Things) and behaviours (e.g. social learning, knowledge sharing, and decision-making). Moreover, it provides insights into how the digital transformation may improve quality of personal life and work life within public and private organisations. The plurality of views offered makes this book particularly relevant for practitioners, companies, scientists, and governments. It gathers a selection of the best papers - original double-blind peer-reviewed contributions - presented at the annual conference of the Italian chapter of theAIS which was held in Naples, Italy, in September 2019.