Employee turnover in traditional industries is starting to hurt organisations as global mobility of people grows and long-serving and experienced Baby Boomers retire to make way for younger generations. Simultaneously, as the population in most countries continues to age, many older adults are faced with dilemmas concerning their future engagement with ongoing employment. For organisations there are manifold challenges with respect to recruiting, retaining and retraining older workers as they endeavour to be competitive in an ever-changing economic environment. This chapter investigates the perspectives of employers and older employees on learning and development within an organisational framework. Learning prospects for workers are necessarily related to this over-arching environment in which organisations are responding to wider societal attitudes and practices towards older workforce membership. Such a framework is nestled within a dynamic global economy in which neo-liberalism has taken hold in many countries. The final section of this chapter discusses learning strategies for individual workers and their employers that are more likely to result in mutually positive outcomes.