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Formal mentoring programs offer benefits such as fostering relationships that facilitate leadership development. However, how the mentoring environment and interactions support the development of these relationships is not well understood. We conducted a design-based, multiple case study to explore how online mentoring relationships develop within a volunteer leadership development program, in a Catholic nonprofit. Online interactions of seven mentor-mentee cases were observed during the six-month program. Data from online discussions, weekly logs, and interview data were triangulated. Mentors were found to use one of three mentoring approaches: coaching, facilitating, or sharing. A sharing approach was found to be more complementary to relationship development and the supports offered by the program. Design considerations are discussed.