The process of technology management contains various stages, such as the identification, selection, acquisition, implementation, and maintenance of technologies. In the case of power generation companies, a key aspect of the selection stage is the choice of generation technologies for newly commissioned units. The investment decision depends on many factors, primarily economic, environmental, social, technological, and legal, and represents a complex multi-criteria problem. Currently, the decision is further complicated by the often unpredictable tightening of environmental standards, forcing the closure of conventional sources, on which many countries have so far based their energy security. The paper analyzes the problem of choosing one of the so-called clean coal technologies to be implemented in conditions of transformation of the power sector. In this paper, five selected clean coal technologies are characterized, and the SMART method is adopted to technology selection. The following technologies were considered: supercritical coal-fired power plant (with and without CCS), IGCC power plant (with and without CCS), and IGCC power plant with CCS and integrated hydrogen production. Nine practical criteria (in three main groups: environmental, technological, economic) for comparing technologies are defined, computational experiments performed, and conclusions from the research presented. The work was based on the literature study of multi-criteria decision support and an analysis of power sector needs based on the example of the Polish power sector. The conducted research, apart from the technology recommendation, led to the conclusion that the chosen method may be applied to decision-making in the field of power generation technology management. The study also indicated the potential direction of the development of a power generation structure in a situation where a component of ensuring energy security is the use of available coal fuels.