Situational and contingency theories will be highlighted in detail, in assessing the most appropriate theory to rely on in setting up an organizational model of leadership. Leadership insights are apparently inevitable in the management roles that an organization’s executive have in steering the organization towards the realization of its objectives. From these two approaches, the theorists assist in understanding the relevant connection to be made between leadership and management, under the inspiration of the organizations’ mission and vision focuses. On one hand, situational theory, Paul Hersey and Ken Blanchard contributions to the effect that styles of leadership styles are not fundamentally important than or superior to the leadership’s response to the varying situation is examined. On the other hand, Fiedler’s contingency theory has been visited in conjunction with the situational theory to illustrate the importance of leadership in the formulation of organizational leadership practices (Kreitner, 2006, p452).In this discourse, I will attempt to find solutions to the question of whether an organization can adopt several leadership perspectives to sustainably tackle all of its challenges. A position held up to the generation of the question is that the organization faces pretty too many leadership challenges such that it cannot be possible to be reliant on a single approach. The choice of these theoretical approaches of leadership was deliberately done to demonstrate the need for the model of organization to depart from retrogressive leadership designs that rigidly fixates the organization to conservative systems inhibiting initiatives. Under the opposing theories of leadership, it is difficult for organizations to respond to the rapidly changing market but reacting to the market only leaves the organization in a poorer condition.