The issue of preparedness of medical students to work as junior doctors has come under increasing scrutiny. One of the key challenge for tomorrow’s doctors is the capacity and engagement for continuing professional learning and development, as well as, appropriate decision making. consequently, medical schools are exploring various ways in which technology can support this and this includes preparing students for work-based learning as well as enhancing the work-based learning placements. This includes the augmentation of the learning process with the development and consumption of digital content and electronic resources of interactive character to support issues around complex problem solving, decision-making and clinical management. Virtual patients and scenario based learning activities as well as the concept of Living Labs may be used in the preparation for the workplace activity, and thus to enhance the effectiveness of medical student work-placements. Mobile learning, reflective learning and coaching tools are being used to support students’ reflections and action planning whilst on work-based learning placements. The scope of this paper is to provide a vision as to how related technologies and associated pedagogical models may be engaged to augment workplace learning and professional development and to digitally empower the medical professional. Emphasis is placed on technology enhanced self-regulation and decision-making for tomorrow’s medical professionals through innovative use cases practiced at the Leeds Institute of Medical Education, in the UK and the Medical School of the Aristotle University of Thessaloniki in Greece. The expected institutional and societal impacts are considered in the relevant timescales of addressing the problem and in view of forthcoming technological innovations