There are two sectors in the Canadian health ecosystem: the public sector, composed of hospitals, and the private sector, consisting of suppliers of drugs and services; both are aimed at providing optimal patient care. Currently, both sectors are struggling with the uncertainty and unpredictability plaguing the health environment. A mentoring pilot was aimed at providing solutions for both sectors by strengthening leadership development and accelerating the relationships with organizations from the other sector. The extra-organizational mentoring program included people from Roche Canada (private sector) and hospitals (public sector) whose participants are members of the Canadian College of Health Leaders. An evaluation of the program demonstrated that it was a positive and productive leadership development process for the majority of participants. The mentoring pilot helped advance partnerships based on trust and respect across the two sectors. The pragmatic process and demonstrable success of the program have gained far-reaching attention, and the program has influenced the development of other mentorship initiatives. Extra-organizational mentoring should be encouraged and actively developed with other health organizations.