The US workforce faces an impending mass exodus of experienced workers as the Baby Boomer Generation prepares to retire. Generation X is entering upper management positions but their numbers are small: approximately half the Baby Boomer population: and they'll be leading Generation Y which is three times their size. This 'age wave' phenomenon has unsettling implications for organizations. Will organizations lose knowledge as their most experienced workers depart? Can that knowledge be captured before they leave? This study examines the differences between the ways member of each generation in the workforce transferes knowledge using semi-structured interviews to understand and diagnose challenges to diffusing organizational knowledge across generational divides. The results indicate that Baby Boomers tend to share knowledge with coworkers in exchange for favors, such as reciprocal knowledge to increase their reputation. Trust is also important to members of each generation in exchanging knowledge, but for different reasons. The Baby Boomers need to trust that a knowledge source will not use shared knowledge to compete against them, the Generation Xers need to trust that the knowledge they share will not be wasted, and Generation Yers need to mtrust a knowledge sources to be credible before absorbing that knowledge.