The work of O. Wesley Allen, Jr. and Ronald J. Allen in the area of conversational homiletics helps a preacher to attend to the stories, concerns, and deep conversations of a congregation with integrity and authenticity. I explore whether such a homiletics combined with the pastoral skill of deep listening, as used during the time with a family preparing for a funeral, allow me better entrée into becoming the minister of a congregation in a new pastorate where there has been a difficult pastoral transition. While many pastors new to a church are allowed a “honeymoon” period, deep listening and conversational homiletics work together to develop sermons that use illustrations from the life of the church, but more importantly, speak to the deeper needs of the congregation. The result is a nuanced success and sets the stage for the future of preaching at this church.