Policies, health, and government regulations affect various Health Care organizations and their members. One such policy, the Health Information Technology for Economic and Clinical Health (HITECH) Act, attempts to improve the performance of health care systems through the use of technology, such as Electronic Health Records (Bluementhal, 2010). The most critical task of leadership is to establish a mindset at the top of the organization and function to infuse a culture of excellence throughout the organization (Bentkover, 2012). Health organizations can only progress if their members share a set of values and are single-mindedly committed to achieving openly defined objectives (Bentkover, 2012). This chapter investigates organizational leadership in relation to health care reforms to include trends in health care leadership, Stratified Systems Theory (SST), Systems Thinking, and regulators perspectives. The chapter will consist of the following sections: background; issues controversies, and problems; solutions and recommendation; future research directions; and conclusion.