BACKGROUND: Virtual activities, hybrid work and virtual mentoring have become part of the ongoing milieu of academic medicine. As the shift to remote mentoring continues to evolve, it is now possible to adapt, refine, and improve tools to support thriving mentoring relationships that take place virtually. This study explores strategies for virtual mentoring as a cornerstone for effective training programs among senior mentors participating in an ongoing mentoring program. METHODS: We conducted a qualitative study among prior and current participants of an ongoing Mentoring the Mentors program about key strategies for optimizing virtual mentoring. Data were coded and analyzed following a thematic analysis approach. RESULTS: Respondents were mostly female (62%), white (58%), and associate (39%) or full professors (32%). We found that, with the expansion of hybrid and fully remote work, there are now fewer opportunities for informal but important chance meetings between mentors and mentees; however, virtual mentoring provides opportunities to compensate for reduced interactivity normally experienced in the workplace. The heightened need to plan and be more deliberate in the virtual sphere was woven throughout narratives and was the foundation of most recommendations. Specifically, a central obstacle for respondents was that spontaneous conversations were harder to initiate because virtual conversations are expected to have set agendas. CONCLUSIONS: Developing new ways to maintain meaningful interpersonal relationships in a virtual training environment, including opportunities for serendipitous and informal engagement, is critical to the success of virtual mentoring programs.