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The very nature of organizational life is transforming as collaborative technologies erase the prerequisite of co-location for collaboration. Using three example cases of which we have been a part, World Vision, the American Society for Association Executives, and Healthy Kids Healthy Schools, we illustrate how such technology is also augmenting the generative capacity of the Appreciative Inquiry (AI) Summit methodology. We then use the five principles of wikinomics that Tapscott and Williams (2010) identify as keys for organizational thrival into today’s digitally connected world: collaboration, openness, sharing, integrity, and interdependence, as a lens for examining how the virtually connected AI Summit is a whole-system change methodology that helps to promote these principles. The chapter concludes with lessons on integrating collaborative technology into summit designs and opportunities for future experiments in this domain.

Intergenerational appreciative inquiry is an approach that maximizes the generativity of all generations and the generative outcomes of intergenerational collaboration. While conversations about intergenerationalism have increased in recent decades, forums and strategies for intergenerational collaboration have emerged at a much slower rate. In this chapter we explore definitions of the concepts of intergenerational and multigenerational and discuss generativity in the context of intergenerationalism. We share how we have found the appreciative inquiry summit, and other appreciative-based processes, to possess a natural capacity for enabling intergenerational inquiry that can maximize generativity. We conclude by turning to the future and discussing generational changes that are taking place in society and why we expect intergenerational appreciative inquiry will only increase in importance as we continue caring for the future together.