The purposes of this qualitative multiple case study were to determine the catalysts and pathways that caused principals to move from managers to effective leaders. Data were collected through a series of interviews with 4 principals who were selected through a purposeful sampling procedure. The interviews were audio recorded, transcribed, and analyzed using inductive coding to determine themes. Findings were presented for each theme within the context of reviewed literature. National polls indicate that 6 out of every 10 of the nation’s schools need major changes or an overhaul. Can improving the skills of their leaders make a difference in the performance of these schools? Research repeatedly supports the importance of a principal’s leadership to the overall success of a school. It also tells us that effective leadership is in short supply and that there is a need to initiate leadership development. The underlying task in this study was to determine how to help those who want or need to become better principals or how they can help themselves. Several themes emerged from data analysis, and each is important to consider when working on improving principals’ leadership abilities: the impact of mentors; university administrative certification programs; on the job experience; personal motivation; tacit knowledge; state, local, and private leadership development programs; and pathways to improvement. Specific recommendations for practices to improve principals’ overall effectiveness included incorporating more and lengthier mentoring in the early part of principals’ careers or as part of performance improvement plans; increasing study of cultural and instructional leadership in administrative certification programs; providing more field experiences in administrative certification programs; and developing individualized leadership improvement plans based on needs, interests, and learning styles of principals. The need for additional quantitative and qualitative research was also suggested.