Incorporating drawings into the assessment process has the potential to facilitate, broaden, and deepen communication. As a unique and flexible method of communication, drawings and the subsequent discussions surrounding them help stimulate participation, build rapport, bridge cultural differences, promote insight, and even serve as an initial intervention. In this chapter, we focus on how drawings can assist clinicians in addressing primary challenges and pitfalls that may arise during mental health assessment. We explain how drawings facilitate expression, organize information, enable change, support engagement, focus assessments, and promote new understandings across clients, cultures, and contexts. The chapter then turns toward a wide range of drawing prompts, including timelines, family and cultural genograms, eco-maps, peer depictions, kinetic school drawings, mood illustrations, problem definition and resolution sketches, and crisis experience portrayals. We also present ways for clinicians themselves to use drawings to gain personal insights.