This paper provides a conceptual overview, coupled with insights drawn from a case-study vantage point. It represents a combined higher education and K-12 research effort ultimately pointing to benefits from extended electronic contact and collaboration beyond graduation. It represents an important attempt to further support new administrators at a point in time when the role of educational leader is only growing in complexity and training programs are struggling to adjust to new accountability requirements and delivery options of their own. This paper is based upon the current and emerging realities within the United States, and advances options that could effectively augment current efforts to support novice leadership at building and higher organizational levels.