With workplaces potentially including four generations, the differing motivations and learning styles provide new challenges to educators, as well as managers and leaders of these workforces. The Net Generation learner of the twenty first century, born after 1980 and digital media fluent, brings potentially greater collaboration and connection to knowledge and learning as a collective, rather than individual, learning process. A postgraduate Masters in Communication course explored immersive learning in two collaborative virtual and workplace-oriented environments. The Net Generation learners were able to identify the connective and experiential nature of their engagement in the virtual scenario and experiential collaborative project as being both transforming and transferable to the workplaces they were targeting through their coursework programs. The case studies explored the neomillennial learning styles as a media-based framework for designing learning tools and environments appropriate for the twenty first century learner.