The study in this article seeks to understand the learning challenges involved in developing learning-centered leadership in schools. It is based on Southworth's (1998, 2004) ideas of leadership for improving schools, which comprise promoting learning-centered improvement at all levels through professional development and a focus on the quality of teaching and student learning. An evaluation of an initiative in New Zealand designed to assist leaders to develop such qualities identified three learning challenges when developing this form of leadership. The first of these challenges was that school leaders did not perceive themselves or their skills to be the target of the initiative, despite being nominated as the focus. The second was that they were more concerned about teachers collaborating with one another than whether that collaboration was leading to improved student learning. The third was that they did not put in place robust organizational processes to support evidence-engaged professional learning. Implications for developing learning-centered leadership are discussed, including the kinds of messages conveyed to leaders about the purposes of initiatives designed to develop such leadership. (Contains 1 table.)