There is dearth of studies exploring the likelihood of reverse mentoring practices being accepted or resisted in diverse organizational contexts. Moreover, prior studies on reverse mentoring have focused on the formal programmatic implementations instead of exploring the informal instances where senior employees learn from their junior colleagues in organizations. To address these gaps, we pose the question: What are the factors necessary for formal and informal reverse mentoring to succeed? We utilized a qualitative methodology based on in-depth semi-structured interviews with 10 globally located learning and development professionals from Asia, Europe, and the Americas who are often tasked with executing mentoring initiatives in their respective organizations. Our findings indicate that reverse mentoring can be successfully practiced both formally and informally if such practices are aligned with the cultural preferences of the context.