Introduction The relationship between culture, collegiality and collaborative learning may appear to be a conundrum to many readers. In this chapter we unravel the conundrum and show its importance for the education of MDV students in this, the 21st century. At its heart is the question: how should MDV students be prepared for a newly emerging society whose structure and form is uncertain? To answer that question, one needs to explore the changes in society, the cultures of MDV Schools and their positive and negative effects upon collegiality and the effects of collegiality upon learning. To complicate matters further, the relationships between culture, collegiality and learning are not unidirectional. Changes in any one of these may have consequential changes in the others. Clearly there can be no simple answer to this question. Rather one can only offer perspectives for readers to consider and reflect upon. The issues are deep.