The Baby Boomers are retiring, and will continue to retire en mass for the next 15 years, so organizations are beginning to invest in Knowledge Transfer Initiatives. These initiatives are helping organizations maintain a continuity of service while helping the younger members of these organizations develop their institutional knowledge. Many of these initiatives are focusing on transferring the retiring Boomers’ knowledge to Generation X and Generation Y, the Millennials. Oddly, one of the most widely accepted generational stereotypes of Millennials is their transient approach to their careers. This being the case, organizations are also heavily investing in curbing this trend by trying to find ways to engage Millennials in their work. Given Millennials’ transient nature and Boomers’ rising retiring rates, organizations are smart to be investing in retaining both their human capital and their organizational knowledge. But do these two initiatives have to live in isolation? This phenomenological research paper examines what the effects of these knowledge transfer initiatives are having on Millennials’ engagement, how Millennials want to be engaged, and recommendations for how organization development consultants can help organizations navigate these two major organizational challenges.