School principals are deemed essential to current school reform, yet the rhetoric about their importance is often unaccompanied by sufficient attention either to what knowledge and skills they need or how they will learn what is needed to effectively lead a school community. This study is part of a larger research project on middle level principalship, designed to explore and further the knowledge base related to the nature of the middle level principalship. Data were collected from 98 surveys and 44 interviews with practicing middle level principals. Research questions included: (1) WHAT do middle level principals want and need to know in order to make the organizational and instructional changes that accompany middle level reform?; (2) WHERE do middle level principals learn?; and (3) HOW do middle level principals learn best? Principals were clear and consistent about WHAT they needed to learn to forward the middle school reform agenda. They spoke about needing further knowledge and skill in: (1) creating a respectful, collaborative, collegial school culture; (2) understanding, implementing, and assessing newly proposed approaches to teaching and learning at the middle school level; and (3) remaining current (up-to-date) organizationally, legally, financially, and technologically. In addressing WHERE they would like to learn, principals are asking for more in-house offerings combined with the necessary incentives for them to pursue the required professional development through graduate coursework and active participation in national, state, and regional middle level association-sponsored programs. Based on the interviews and the literature surrounding professional development, the middle level principals were able to describe HOW they learn best: (1) identification of needs and involvement in planning; (2) reflection within the school context and sharing with other colleagues; (3) systematic development supported by district time, money and resources; and (4) competent instructors using practical, adult learning processes. Most of the interviewees acknowledge that understanding practice is an important precondition for improving practice and that an integral part of improving the effectiveness of the school necessitates that professional development be an ongoing process. However, as Little (1993) reminded us, the process is complicated, takes time, and requires models of good practices and coaching support. It works best in the company of others and in an environment that encourages risk taking designed to improve student learning.