Collaborative drawing is a multimodal approach to examining problems within small groups of individuals when the perspectives of multiple stakeholders should be considered. Collaborative drawing can be useful for helping students visualize and analyze a challenging problem from different world views and provide opportunities to confront, discuss, and identify potential resolutions. Rich Pictures (RPs), the artifacts created through collaborative drawing, were used in two fourth-year undergraduate internship classes (n = 48) to prompt student discussion about potential workplace dilemmas and provide a site for reflecting on professional challenges. Students used graphic objects, icons, and stick figures or 'actors' playing distinct roles, to map out a problematic workplace scenario. The RPs created by the students illustrated the emotional complexities inherent in complex problems through spatial organization, commonly used symbols and emojis, and narrative vignettes. The RPs provided a space for students to "surface" their emotional responses to the problem scenarios, examine the inherent power dispositions, and illustrate the nuanced and complex perspectives to consider in professional environments. The findings contribute insight on multimodal strategies for facilitating opportunities for students to develop their professional identities, and present innovative methodologies for researchers in Higher Education to study that development.