The healthcare sector is undergoing a transformation to become data-driven, following the footsteps of other industries. Technology trends are emerging, but other factors related to data gathering and stakeholder involvement can enable or hinder the change. The digital transformation of healthcare is crucial to achieving quality, access, and efficiency objectives. However, the healthcare industry lags behind sectors such as media, financial services, and wholesale trade in global digitalization. Over 50% of the Italian population prefers to see a doctor in person rather than remotely, and people miss human contact when interacting with AI systems. Healthcare facilities approve few digital initiatives, and many have not introduced new technologies in their strategic plans. The digital transformation of healthcare is a complex process that requires a holistic approach, involving all stakeholders and addressing the challenges related to data collection, analysis, and human interaction.