The study of generational leadership differences has now broadened and intensified to an impressive body of literature and discussion. The problem is that the conversation continues to be framed as a demographic challenge of difference, which only furthers the division, rather than a relationship challenge that calls for new ways to connect the generations. This article discusses the nature of the relationships needed to ensure vital connections between generations of leaders. It uses the authors' own cross-generational leadership relationship as a case study in what we believe exemplifies the kind of relationship our research suggests is both needed, and desired, by leaders in both incumbent and emerging leadership generations.