The twin processes of collaborative inquiry and generative dialogue underpin two closely aligned and increasingly influential school leadership development programs, one in Alberta, Canada, and the other in New South Wales, Australia. This paper focuses primarily on the Australian program, the character of which has been strongly influenced by its Canadian predecessor. Of interest in the paper is the nature of the foundations of collaborative inquiry and generative dialogue, and the relationship of these processes to an expressed need for better leadership development in the Australian school sector. David Townsend and Pam Adams, who are principally responsible for generating a school leadership development model based on the use of both collaborative inquiry and generative dialogue, have sought to show how these two processes should function seamlessly, but there is more to be said about the nature of their relationship. This paper seeks to throw more light on the integral role played by generative dialogue in empowering collaborative inquiry in the context of school leadership development.