This thesis addresses questions that stand at the intersection of the ministry of preaching, the church's vocation to make disciples and initiate them into the Body of Christ, and the formation/transformation of congregations in an early Twenty-first Century, North American context. Acknowledging the importance of the ancient Catechumenate's retrieval and adaptation for our time, the author suggests that its promise remains unfulfilled in many ongregations because they are locked into a self-understanding still rooted in Christendom and uncritically shaped by the individualist and consumerist presuppositions of the dominant culture. Such settings, he observes, are ill-equipped to initiate inquirers/seekers/candidates into a church characterized by a strong sense of ecclesial identity and vigorous participation in the missio dei. He contrasts this posture with that of the church in the Second and Third Centuries of the Common Era described by Alan Kreider in his book The Change of Conversion and the Origin of Christendom. The operative understanding of conversion in pre-Constantinian Christianity, as articulated by Kreider's analysis, is advanced as a promising orientation for preaching that aspires to shape fresh ecclesial self-understanding and renewed missional vitality in the contemporary community of faith. Drawing on research conducted over a period of nearly three years in a mid-size congregation of the Anglican Church of Canada in London, Ontario, the author describes qualities of preaching and preachers that foster the ongoing conversion of the church and support congregations in the work of Christian Initiation.