A little over a year ago, Sheryl, one of the authors, became a principal for the first time. Her transformation from education professor to elementary principal represented a significant and unusual career progression. Gayle, one of the authors and an elementary school principal for 11 years and a curriculum specialist and classroom teacher for more than two decades, became Sheryl's mentor. This article describes how they navigated their mentor-mentee relationship through e-mail exchanges. The authors discovered that a steady stream of e-mail communication containing necessary knowledge, authentic feedback, and mutual and sincere caring can build a strong foundation for an effective mentorship. School districts should not underestimate the support e-mail mentoring can provide for novice principals.