Based on the author's great privilege to have known Mike Rosenak over many years as a conversation partner on issues of Jewish though, Jewish education, and the contemporary Jewish situation, he presents an issue of current concern in the philosophy of Jewish education and considers the response that Rosenak might offer. Directly and indirectly, Rosenak may have already offered his response in his book, "Tree of Life, Tree of Knowledge: Conversations with the Torah" (Rosenak, 2001). The question the author has pertains to Jewish leaders and teachers (for example, campus Hillel rabbis) who are committed (a) to the strengthening of Jewish life in their communities and beyond, and (b) to the strengthening of the Jewish lives of individual Jews (students, for example) but are committed no less (c) to a "vision of Judaism and Jewish life that crosses ideological and denominational boundaries." How can such leaders and teachers, speak cogently and forcefully about Judaism to Jews and in particular to emerging Jewish adults, or varied conviction and direction? In this article, the author draws upon lessons offered in Rosenak's "Conversations with the Torah" to explore answers to this question.