Today, the Vocational Education and Training (VET) curriculum in Greece is state-regulated, combining school-based and work-based learning, and it is offered at upper-secondary and post-secondary levels. There is a need to prepare a new agenda for VET in Greece that follows the rapid technological developments of today. Our paper aims to enrich, redefine, and expand the current curricula and educational practices while proposing a complete plan for the overall reformation of VET’s learning conditions from the point of view of teaching and learning analytics. Through the evaluation of the existing changing institutional framework, the updated bibliographic references, and the experiential data of the educational reality, we can understand the expected needs of technological educators and decide how to address the priorities that must be determined. We focus on the preparation of the trainers and the overall redefinition of the role of education in preparing graduates. This paper’s main conclusions offer interpretations for the cognitive orientation of the existing curricula, as well as direction for the thinking and teaching skills of teachers, to build confidence in the prospects of technical education in Greece.