Transformation is how adults make meaning from and interpret experiences. Transformation know-how is an important attribute to demonstrate while leading. This paper examines the transformational ability of leaders. It is generally perceived that since leaders have similar leadership skills, the perception of how they transform their organizations into learning organizations would be uniform. Expectations directly influence meaning and how the perspective changes to accommodate the new experience. This could be attributed to factors like a leader's educational background, experience in a complex organization, or exposure to successful change efforts. This study attributes specific leadership experiences and perceptions toward the ability to transform an organization. Critical success factors are sound awareness of transformation, the courage to engage in a disoriented dilemma, to accept the knowledge that a perspective requires new understandings of those who lead at all levels within the organization, and the ability to articulate the strategic direction and gain the motivation and engagement from all stakeholders. Four leadership skills are found in the literature that acknowledges transformational leaders have similar skills and perceptions on transforming a traditional organization into a learning organization: a) sense of urgency, b) envision a new vision, c) catalyst for a cultural shift, and d) strategic thinking.