This research is a qualitative study that investigates succession planning management in four (4) Kentucky healthcare organizations as it relates to the changing workforce demographics. In planning for the 21^st Century workforce, organizations are becoming increasingly aware of the aging workforce and implementing strategies to develop career development programs to identify and develop employees for middle and upper levels of leadership. America’s workforce is aging with large numbers of employees eligible for retirement. The supply of future workers and leaders within healthcare organizations is dangerously reduced if healthcare organizations do not plan for the large numbers of employees eligible for retirement. This study analyzed the trends expected to impact healthcare organizations as leadership transitions occur among an aging population and workforce. This research study examined how four (4) Kentucky healthcare organizations identify potential leaders; use mentoring to address succession plans; retain employees and prepare for workforce diversity; and develops leaders within the organization. A major finding of this study was the consistency among all four participant organizations. The findings reflect the need for healthcare organizations to create formal succession plans to address workforce and leadership shortages. The study reveals that none of the participant organizations have formal succession plans, and leadership development training is in the infancy stage of development. The implications for healthcare organizations are significant and demand action now. A crisis in healthcare and related organizations can be alleviated if leaders take action to address the aging and shrinking workforce and plan for leaders using mentoring and formal succession planning.