Population ageing is a phenomenon that is quite new and irreversible in the history of mankind. Every country and every organisation is concerned while it is not certain that all the risks and challenges have been clearly identified. Clearly, there is a risk of massive knowledge loss, i.e., “Knowledge Crash”, due to massive retirements, but not exclusively for this reason. This risk is not evaluated at the right level, and in this regard, this article, by including the problem of “Knowledge Crash” in the more general framework of “Knowledge Management”, enlarges the concepts of knowledge, generation, and knowledge transfer. The author proposes a global approach, starting from a strategic analysis of a knowledge capital and ending in the implementation of socio-technical devices for inter-generational knowledge transfer.