The construction sector has begun to embrace the digital revolution, intending to improve efficiency. How, on the other hand, should the industry adopt digital tools? And how should the connection between humans and technology function? This study aims to shed light on how the construction sector may bridge the gap between AI deployments’s potential and realized advantages. This article presents research based on a comprehensive review of the literature, case studies of Speller Metcalfe, a design-build and refurbishment project in Malvern, England, Jacobsen Construction, a project digitizing the planning process in Salt Lake City, Utah, USA, and Menkes Development Inc., real-time visibility to construction site insights and data-driven decision-making in Toronto, Canada. The experiences gained via this study show that it is feasible to acquire expertise while adopting sophisticated technologies, such as artificial intelligence, by installing fundamental digital tools (AI). However, when it comes to AI, the level of trust between humans and machines will be the deciding element in its success. This article is a pioneering effort in examining the deployment of AI and how people and technology should interact. This study is limited to three case studies and three digital technologies. To further the study, it is suggested to debate the adaptation of AI on the user's premises, gather more empirical data, and examine case studies from different sectors.