Diversity concept tends to change in the last decades and nowadays constitutes shifting to unresolved challenges of forcing digitalization and trending ageing. Results showed that in higher education not only digital upskilling of older academics and boosting collaboration between younger and older academics is needed, but also breaking the myths that accompany older workers. The Czech Republic and Ukraine face similar challenges regarding the digital divide, including the need to upskill their older academics to adapt to digitalization. Higher education institutions need to develop strategies tailored to each country’s specific conditions, considering the diversity of their staff. It can be achieved by setting clear goals and a diversity management strategy for universities and research organizations taking into account ageing and digitalization trends. The formation of collaboration groups that bring together younger and older workers, as well as through the organization of internal training and courses, is designed to meet the needs of older workers. Lifelong learning is the most crucial principle in this process.