The article discusses the learning and technological challenges essential to bridge the generation gap of training multigenerational workforce. It suggests organizations to accept generational differences and provide multiple training options, communications and tools so that each generation will achieve its goals. It is essential to place experience employees in transforming the institutional knowledge, and communication must be tailored according to generation's individual styles. Training staff needs organizational support as well as additional training to have a better understanding of their role as well as design instructional content in new formats.