This chapter attempts to review some of the possible implications for leaders and managers as they and their organisations come to terms with a dramatic shift in the age profile of workers. Previous generations would largely have seen older workers, long in tooth and heavy with experience, passing on their knowledge and wielding legitimate authority over younger, less experienced new employees. This hierarchy largely reflected that of society with political, business and social leaders being older than the majority of their followers and subordinates. However, with older workers remaining in the workplace and millennial employees entering the workplace with a set of values that differ, this steady state relationship has been transformed—may be even turned on its head. The chapter steers away from the mire of trying to define ‘leadership’ and instead looks at some of the practical managerial and leadership challenges facing inhabitant of a modern organisation. There is an exploration of themes around the impact of digital communications, brand values and how to build positively on the generational gap rather than viewing the situation as a problem to be solved.