We live in an era of unique challenges requiring us to face a new reality mired in information overload for the 21st Century. This new reality emphasizes the critical need for educational leaders who can think and act systemically rather than bureaucratically. The bureaucratic model inherited from the Industrial Era still prevails in many educational organizations, and consequently the leader's role is defined by the structure and function of this model. Deviation from the bureaucratic model requires leaders who are systems thinkers and who can effectuate necessary sustainable change and innovative practice within this model. In this article we discuss (a) the concept of systems thinking to promote organizational change within a bureaucratic model, (b) the role of adult learning theory in the process of change, and (c) the use of Cambourne's Conditions of Learning (1988) as one model for developing the personal reflection that may lead to achieving sustainable change within the system.