Countries of the EU are trying to create a single digital market. Therefore, this article aims to evaluate the current situation in the field of readiness of economic entities in Slovakia for challenges in the field of human capital management (HCM) when implementing digital technologies in their processes and to propose recommendations regarding the implementation of digital technologies. We used basic scientific methods and calculated Cronbach’s alpha, descriptive statistics, and the chi-square test to detect dependencies between variables. This article processes data from a questionnaire survey completed by managers or owners of economic entities in Slovakia. In 2020, we received answers from 905 respondents, and in 2021, our sample consisted of 561 respondents. We found that among the most used is digitalization in the field of GDPR and not the use of a personnel information system (HRIS). The assumptions that the size of the entity and the prevailing ownership influence the use of digital technologies were also confirmed. The article’s originality lies in the topicality of the examined issue and the extensive questionnaire survey spanning two years. It follows from the findings from previous articles, which pointed to the extremely low values of Slovakia within the DESI index.