The hybridity and dynamism of today’s interconnected, interdependent and culturally diverse world poses challenges and opportunities for learning and communication. This book introduces an approach to facilitate global learning opportunities, while facing these challenges. The approach is based on the cage painting metaphor for dialogic co-construction of meaning, and understanding of multiple perspectives. Resolving disorienting dilemmas or preconceptions requires a dialectic flow of thinking since the root of the problem may lay deep in person’s beliefs and values. Such experiences might be transformative in their nature, causing change in person’s perspective; better understanding the culture of themselves and other people; reflective and mindful inquiry into one’s worldview; the third place processes. Misunderstandings are more prevalent when using technology—global reach—between people from distant locations different cultures. To prepare people for these challenges, we offer a Web 2.0-based instructional design blueprint. Dependent on the context and content of the planned activities, the cage painting and global learning processes may be facilitated simultaneously or sequentially. The approach presented in this book has attracted interest of educators in different disciplines as well as human resources leaders concerned with key characteristics of today’s global business workers: intercultural/global communication and collaboration. The ideas emerged from six years of studying ways in which we and our colleagues from 25 other countries integrated global learning into classrooms in a range of discipline areas. In this book we explore the competences needed to communicate interculturally and avoid the effects of preconceptions on our communication and collaboration. We review metaphors commonly used in intercultural communication and then introduce a new metaphor called "Cage Painting". The process of Cage Painting requires certain conditions during intercultural communication, whether it is face-to-face or via global reach, using technology. The transformative processes that we undergo as we confront cultural disorienting dilemmas, smiling being a simple example of one, are named the Third Place.