This study explores the similar and different developmental influences that shape the practice of beginning and advanced spiritual directors. An examination of the contemporary literature on spiritual direction finds that in the main, two developmental influences shape the practice of contemporary spiritual directors: their capacity to adopt a contemplative stance towards their directees and their ability to be aware contextually of the factors that fashion the dynamic of accompaniment. While the review highlights the presence of these two influences, the literature is deficient in understanding the similarities and differences in how these two influences shape the practice of beginning and advanced spiritual directors. To address the deficiency, this study reviews three groups of Western Australian spiritual directors, Anglican, Churches of Christ and Roman Catholic. The investigation takes a qualitative, ethnographic approach, using focus groups. An analysis and discussion of the data confirms that the similarities and differences in the influences that shape their practice revolve around two key developmental influences namely, the capacity of directors to adopt a contemplative stance to their directees, and their ability to be aware contextually of the factors that fashion the dynamic of accompaniment. While both influences shape beginning and advanced directors, the former impacts more on the practice of beginning directors and the latter more affects advanced directors. Two factors may initiate and sustain the capacity of directors to adopt a contemplative stance. First, directors grow by noticing and attending to all the dimensions of their human experience. Second, directors develop by having their experience attended to in some form of therapeutic relationship or through participation in various developmental group processes. Directors may enhance their capacity to be aware contextually of the factors that fashion the dynamic of accompaniment through understanding paradigms about spiritual direction practice and spiritual development. Their appreciation of paradigms about spiritual direction may derive from two sources. The first is by how they distinguish more effectively spiritual direction from other therapeutic practices. The second is by how they grow in understanding relevant theological, philosophical, and psychological perspectives that inform good practice. Directors may further increase their comprehension of interpretive frameworks about spiritual development by redressing the attitudinal effects of fundamentalism and incorporating a multiplicity of approaches to spirituality. Training programmes are an important means to introduce and develop directors’ abilities to be aware contextually of the factors that fashion the dynamic of accompaniment. A person’s ecclesial role may influence the context in which a director commences practice. From this discussion, this study draws conclusions and offers recommendations applicable to practice and research.