This study explores how Cuban healthcare organizations are planning for the next generation of leaders through succession planning strategies. This study analyzed three critical factors which influence succession plan: organizational awareness on the necessity of the succession plan, labor market condition to supply qualified candidates, and conducive environment. Employing ethnographic interview with a focus group, this study identified critical obstacles to impeding effective succession planning in the Cuban healthcare system: lack of awareness of the effective management; structural constraints in nourishing healthcare administrators and leaders; the dearth of incentives fulling young, motivated health professionals. Nevertheless, free education for health professionals, anticipated changes resulting from the US opening an embassy in Cuba, and the burgeoning NGOs in the new era of post-globalization would provide the Cuban health system with new opportunities. This study recommends that the Cuban healthcare system develop a managerial track is distinct from the clinical route and that it expand partnership with international NGOs for tackling sustainability problems. The Cuban health system should develop succession planning strategies, using flattened and flexible organizational structure, people-oriented workplace culture, proactive human resources management plan, and restructured medical management and innovative and transformative leadership program open to all health professions.