Introduction According to Schermerhorn et al. (2014, p. 74), “Organisations are made up of people, each of whom as a unique individual. An important key to competitive advantage is respecting this diversity and allowing everyone’s talents to be fully realised”. This paper seeks to show the fundamental challenges that exist in organisational management in cases where staff membership consists of a multi-generational workforce. A number of articles and books on employee management and human resources address the issue of a multi-generational workforce (Millar & Lockett, 2014). Lyons and Kuron (2013) explain that the term “generation” in the context of human resource management deals with wider social trends. The social forces’ perspective shows that generations take shape within the flow of history. Meanwhile, a cohort perspective is also sufficient as a background framework for understanding the appropriate ways of dealing with multi-generational workforces because it links behaviours and characteristics of a group with its age. With “a shared inborn way of understanding life”, as explained in the Manheim’s theory, Lyons and Kuron (2013 p. 140) show that workers of the same generation across industries develop a universal consciousness and react in the same way to different historical events. For example, baby boomers and people born after the World War II and before the mid-1960s experienced similar global historical events and have a shared consciousness that affects their view of work and values in life. The social history of a specific location also shapes the characteristics of a particular location’s workforce. Thus, there are subtle differences in the generation of baby boomers in North America compared to that of South-East Asia. What key challenges exist when managing multi-generational differences in the workforce: A case of Baby boomers Issue 1: Deferring Retirement Many countries have resorted to analysing their current workforce as a response to the challenges facing their economies. According to Helyer and Lee (2012), the European Union workforce will continue to age from the year 2010 to 2060. An aging workforce is a cost burden for most firms, as they have to readjust their strategies on human resources. Currently, many members of the baby boomers generation are deferring retirement. One of the reasons for the deferment is the sufficient health care and workplace technology that allow them to continue being productive in various capacities. Baby boomers who reach the retirement age keep working as a way of coping with the overall rising costs of living in many countries. Additionally, a big number of baby boomers are also staying on their jobs because of personal fulfilment, job satisfaction, and social interactions (Helyer & Lee, 2012). Having an aging workforce that is not keen to retire is a good thing for other organisations because young people who are entering the organisation have an excellent opportunity to learn from their older counterparts (Helyer & Lee, 2012). On the other hand, the delayed retirement of baby boomers is causing distress among young people and the baby boomers generation members who are impatient and want promotion and more responsibilities at work. As baby boomers increase their skills through training and their work experience, they increase the requirements for employment of new workers. Consequently, members of the Generation Y born between 1979 and 1