Purpose: The purpose of this paper is to highlight challenges and opportunities that surround the process of intergenerational learning and knowledge transfer. Several options in this regard have been discussed from the managerial and employee perspective. Design/methodology/approach: The systems approach has been implemented to identify options of intergenerational learning and knowledge transfer that could be valuable when developing a strong individual and organizational body of knowledge with the purpose to avoid the "knowledge crash." Findings: A review and analysis regarding intergenerational diversity, especially in the light of information and communication technology and social media, has been proposed along with the discussion on possible intergenerational knowledge transfer practices and methods of developing learning agility in all generations though engaging in internal mobility and building communities of practice and learning. Research limitations/implications: Conclusions and remarks provided in the paper need further empirical testing and validation. Practical implications: Implications for practitioners, especially mangers, have been identified regarding recommendations for implementing intergenerational knowledge transfer solutions which could benefit all stakeholders--not only younger and senior employees but also managers responsible for pursuing enterprise development based on continuous learning and knowledge sharing. Social implications: Implementation of suggestions provided in the paper regarding intergenerational knowledge transfer and learning could result in significant benefits in terms of less intergenerational conflict and stress and greater organizational working cohesion as well as further advancements in organizational learning and knowledge management. Originality/value: Challenges that surround the process of intergenerational learning and knowledge transfer have been identified along with options to manage this complicated and often delicate processes from the managerial and employee perspective.