The paper focuses on the analysis of the digital skills gaps in the ageing workforce and factors considered by the ageing workforce as the most important for them to remain competitive in the labor market. As the ageing workforce struggles to adapt to a new, fast-changing environment, especially in the use of digital technologies, their training and education are crucial. This is an important concern in Slovakia, where the workforce in the 50–64-year age group represents 18.70% of the workforce. The paper is based on original data collected from a representative sample of 150 respondents from Slovakia in this age group in fall 2024. The paper explores key digital skills identified by respondents as ones that they need in the workplace and need to improve. These include digital tools for office use, cybersecurity, use of video and teleconference tools, visualization and analytical tools, effective digital file management, and knowledge about AI and its use in the office environment. The lack of such competencies is also observable in the DESI index, where Slovakia ranked 23rd out of 27 EU members in 2022. The original research conducted by the authors clearly indicates that this demographic group is lagging behind in both using and understanding digital technologies.