The International Leadership Association's "Guiding Questions: Guidelines for Leadership Education Programs" (Ritch & Mengel, 2009) provides a framework to attend to leadership program development, redesign, evaluation, organized program review, questions concerning academic legitimacy and developing common program benchmarks. This article provides a critique of the "Guiding Questions: Guidelines for Leadership Education Programs" and, in particular, the five major categories: Conceptual Framework, Context, Content, Teaching and Learning, and Outcomes/Assessment. The article also draws upon scholarly research within the field to provide both breadth and depth to the different "Guiding Questions" categories. Finally, the goal of this article is to encourage a collaborative dialogue which will ultimately increase the effectiveness of the "Guiding Questions."