Technological revolution brings forth major changes in the labour market as well as the necessity to adapt to the shifting conditions on the part of both employees and entrepreneurs. This notion fits in with the European Policy of “Lifelong Learning” which presents the necessity to constantly improve skills and participate in the process of learning through the entire period of professional engagement. The aim of the article is to diagnose the current situation in the labour market and expectations towards employees as a result of the technological revolution and digitization, and to analyze whether there are groups of countries in the EU with similar features describing the labour market and to present the differences between these groups. The study uses research methods based on literature research, content analysis and comparative analysis, and the empirical part uses cluster analysis—the Ward method, using secondary statistical data from the Eurostat database. It was verified which groups of the Member States exhibited similarities to the extent of: forms of employment; work productivity; commitment of entrepreneurs and employees to the process of continuing vocational training (CVT) and lifelong learning; educating future employees of the economy at the level of higher education (HE) in STEM fields and development of digital skills as well as commitment of governments of each EU Member State to financing research and development in higher education institutions (HEIs). It may be ascertained that the average values of variables describing the pattern followed by “new” Member States which joined the EU in 2004 or later are, in majority, lower than the values of the same variables describing the pattern followed by the “old” Member States. It cannot be unambiguously stated that the affiliation with the Eurozone in any way determined whether a given group of Member States is better or worse than the other. The resulting figures may become significant at the stage of developing the employment policy as well as the education policy and the professional career development policy in the respective Member States. Those results may be applied to both evaluation and planning of actions to be taken against the background of the development strategy in order to reduce clearly visible inequalities between the European Union Member States.