Thoughtfully designed arts initiatives can create experiences that respond to the emotional and psychological needs that arise following disaster and trauma, foster agency and connection, reveal pathways toward recovery, and strengthen the conditions that enable individuals and communities to heal. Evaluation is a critical part of that design process, helping us clarify what an initiative is intended to achieve, understand what it needs to be effective, listen to both affirming and critical voices, adapt as the work unfolds, and identify lessons for future practice. Using Power of Art: Inspiring Community Healing After Gun Violence as a case example, we will explore how art and evaluation can work together not only in response and recovery, where these efforts typically live, but also in preparedness and prevention, and invite the audience to consider how we can all contribute to transformative change.