This investigation concerns school leaders' perceptions regarding the efficacy of a leadership development initiative implemented across schools in the North Coast region of New South Wales, Australia. Based on an Alberta school improvement process, the North Coast Initiative for School Improvement sought to achieve leadership development and improved learning outcomes through use of the processes of collaborative inquiry and generative dialogue. Five schools were selected for an exploration of experiences within the Initiative. Accounts provided by the interviewees pointed strongly to the achievement of positive outcomes. The participants referred particularly to benefits in the form of increased leadership confidence and capability. Success factors underpinning the Initiative include: the twinning of collaborative inquiry as a process for improving professional practice with the process of generative dialogue to achieve more effective conversations, and; the nature of the Initiative, itself, where, facilitated by a visiting leadership team, professional colleagues meet monthly for deep discussion about professional issues they share.