Mentoring, as a model for supporting professional growth and development and career advancement, has had varying degrees of success in a wide array of organizational and private contexts. However, its critics might argue that it is one-sided, with the mentor squarely placed in the role of expert who guides the mentee as learner from the mentor’s platform of expertise and personal experience. While the benefits of such a model are well documented, there is reason to believe that neither the mentor nor mentee is positioned to derive the full benefits of the relationship as it has been traditionally defined. Further, there is something quite remarkable that remains untapped in the traditional mentoring model. In this paper the traditional notion of mentoring is challenged, and a new model that showcases the mentoring relationship as a dynamic inter-developmental process that fosters the co-creation of knowledge is presented. Moving beyond the role of mentor as helper and guide and mentee as learner, the authors describe a powerful case study that illustrates the role of humility in re-defining the boundaries of mentoring to foster the co-creation of powerful transformative impact. Recent research in leadership humility and transformative learning is referenced, providing an evidence basis for the model that is presented. A checklist for action that can inform the design of more impactful mentoring relationships is offered.