A vast majority of existing literatures and researches pertaining to generational diversity in an academic environment have always capitalised on pedagogical aspects and the interplay of each generation's distinct culture and characteristics in a teaching and learning context. While such focus is undeniably necessary, another area that requires to be circumspectly investigated is the manner by which generational diversity affects workplace interactions and relationships in an education-oriented workplace context. This paper explores this possibility by looking at comparable researches conducted from other industries and its parallelism with an education focused workplace is inferred. Furthermore, the three diversity management paradigms proposed by Thomas and Ely (1996) was utilised and its implication to educational leadership is propositioned.