Over the last two decades, the roles of academic nursing leaders have undergone significant change and have become increasingly complex. Nursing deans and directors are charged with overseeing the daily operations of the organization (budget, facilities, and human resources), sustaining the school’s central missions (teaching, research, practice, and service), and representing the school within the greater university and with external constituents. The role requires working with many different stakeholders (frequently with competing demands and often involving complex circumstances). Successful deans find a balance between meeting expectations of the president and provost by upholding institutional policies and regulatory requirements, supporting faculty governance, meeting faculty expectations, and addressing the interests and needs of community stakeholders. Nursing deans must have a solid understanding of the various components of the role, as well as the multidimensional contexts in which they reside, such as the rapidly changing landscape of healthcare and higher education.