Due to the current situation of lock-down and social distancing, many educational institutions have shifted to online learning. This study aims to identify the key factors that should be present for successful online discussion and explores the advantages of merging two activities, e-mentoring and online discussion, to improve the quality of the online discussion. A mixed methods design-based was conducted in the setting of the online program in health professions education. Several success factors were identified by the current study: merging of mentorship and online discussion, shifting of roles, structuring of the discussion, assessment, and the use of guides. The study also magnified the role of supervision as moderation and mentorship and suggested solutions to deal with silent participants. Finally, the use of a student guide and shifting of roles between the students play a crucial role in the success of the ODFs.