The burden of illness related to diabetes and its complications is exceedingly high and growing globally. Systematic approaches to managing chronic care are needed to address the complex nature of the disease, taking into account health system structures. This study presents data collected from interviews with physicians, health system administrators, and other healthcare staff about chronic care management for elderly people with diabetes co-morbid with other chronic conditions in light of new programs intended to reduce barriers by incentivizing care encounters that take place through telephone and electronic communications (non-face-to-face care). Results indicate that health system personnel view non-face-to-face care as potentially providing value for patients and addressing systemic needs, yet challenging to implement in practice. Barriers and facilitators to this approach for managing diabetes and chronic care management for its complications are presented, with consideration to different types of health systems, and recommendations are provided for implementation.