Entering into a dialogue facilitated by drawings is essential to the design process and essential to the success of the designer. The role that drawings play as a part of a critical dialogue and within conventional conversations about design and architecture will change as designers and architects adapt to new challenges and opportunities. As new roles take shape it is useful to consider how drawing as a dialogical tool can inform innovation, articulate new technologies, and propel research into new areas of inquiry. Early in their studies, students will sometimes respond with diffidence when asked to produce a series of drawings representing multiple approaches to a design problem. There are several reasons for this lack of confidence. First, is that for many students, their experience in school has not included the opportunity to present an original idea. Second, is that students with prior drawing experience often arrive with experience drawing from observation rather than experience drawing from the imagination. Third, is that students are typically not well-versed in three-dimensional visual systems, and fourth, is that students are trained to think that there are right and wrong answers to simplistic questions rather than to develop multiple answers to complex problems, with each answer having its relative merits and deficiencies. By addressing each of these four issues in the culture of the design studio students will develop their drawing skills in line with their conceptual and intellectual development, and will learn to engage others in dialogue through drawing.