The research aims to explore the outputs of the training systems, aiming specifically at the evaluation of the trainees' transition to employment and the “reading” of the dynamics exhibited by this interface. The target population was graduates of initial and continuing training during the period 2008-2009 and was investigated with mixed methodology. The problematic and the research hypotheses documented data such as: a) the economic and financial crisis in recent years affects Greece, with what bad stuff this entails for Greek workers, unemployed, young people and socially vulnerable groups, b) the admissible common view on the ineffectiveness of the role and training mission in Greece, c) the low degree of connection between vocational training and employment, d) the prospects and challenges that the Greek society will face in the European context and e) international upheavals and pressures at European and international level adjustments of national education and training systems under the weight of neoliberal globalization. Through the research findings highlighted the constant request for improving the quality of vocational training systems in Greece, the low connection of vocational training systems to employment, the low degree of retention of employment, the general frustration of trainees from the obvious weakness and ineffectiveness system to give solid access to work and the low use of the knowledge obtained from training to work. Finally, it was noted that active employment promotion policies are required, which relate to the imperative challenge of structural reconstruction of the country's productive fabric.