The retirement of baby boomers is now a reality and an ageing workforce presents challenges to organizations as valuable talent leave (Armstrong-Stassen & Ursel, 2009; Calo, 2008; O’Brien-Pallas, Duffield & Alksnis, 2004; Paullin & Whetzel, 2012; Rappaport et al., 2003). Is it simply a case for increasing the legal retirement age (O’Brien-Pallas et al., 2004) or does it require a more focused approach to retaining talent while planning for replacement (Calo, 2008; Paullin & Whetzel, 2012; Towers Perrin, 2005)? In the same vein, in order to design programmes for retention, it is important to understand what motivates the older generation to work. A Towers Perrin survey (2005) revealed that a growing number of companies do indeed analyse their workforce demographics and implement targeted strategies and programmes to recruit and retain age 50+ talent and, most importantly, capture the knowledge of workers approaching retirement. Retention here is part of a phased retirement programme designed for smooth workforce planning (Calo, 2008). A flexible retention strategy can focus on the older employee’s ability to physically and cognitively perform required meaningful work and perception of financial and health security (Paullin & Whetzel, 2012). A generational empathy environment serves to decrease the potential of perceived ageism which can reduce engagement (Armstrong-Stassen & Ursel, 2009; Rappaport, Bancroft & Okum, 2003), while intergenerational mentoring can facilitate skills retention for succession planning following retirement (Calo, 2008; Paullin & Whetzel, 2012).