The 21st century is typified by massive technological changes in modes of communication that do not necessarily translate into improved communication between individual stakeholders. Employers expect graduates to be competent in 21st-century skills like communication as well as other skills that relate to communication, such as creativity, innovation, collaboration, leadership, and responsibility (Lai & Viering, 2012; The Foundation for Young Australians, 2018). In order to develop communication in all its complexity, it is incumbent upon educators to create a safe space in which students can learn to communicate collaboratively (Kolb & Kolb, 2005) in the culturally and linguistically diverse classrooms that typify Australian postgraduate study. In this class, students are exposed to different ways of working and learning as they navigate together the subject of communication in organizations. Our scaffolded activities challenge students but allow them time and space to find solutions and ways of thinking that have been previously unknown or unexperienced (Hase & Kenyon, 2007). Whilst seemingly constrained by the various regulatory bodies that quality assure our teaching, we can be flexible and reflexive by introducing our students to experiences in how to communicate across oral and written modes. This chapter offers educators a guide for encouraging cross-cultural communication within an organizational communication subject, as it challenges students to examine how they learn in complex and collaborative environments and what capabilities, knowledge, and skills they need to develop for their future careers.