Guided opportunities to look at art, and then talk about it, allow us to express and process emotions and cultivate wellbeing. HHart of Medicine, a program of H+H, New York City’s massive public health system, uses art to help clinical and non-clinical teams become more comfortable with one another, increase awareness of patient and caregiver experiences, and strengthen their powers of observation, an imperative for accurate diagnoses. This workshop demonstrates how those techniques can be adapted more widely to give participants space to reflect, promote empathy, and deepen their understanding of how others experience the world.