For an academic unit to remain relevant, it must continually evolve. This paper provides a rare view into the process taken by one academic department embracing change to improve its communications and envision its future. Tasked with planning a departmental retreat, two faculty members designed a series of activities inspired by design thinking to prototype new ways to problem solve. This paper describes the activities used before and during the retreat, why these activities were designed, and shares reflections from the facilitators. Three rounds of online Delphi-style information gathering preceded the day-long retreat to build consensus and prioritize issues. Retreat activities followed the empathize, define, and ideate design thinking stages. Based on online anonymous surveys, facilitator reflections, and artifacts gathered, this paper offers a case study from one department discovering that change requires intentional effort and practice but can spark new possibilities. Limitations and future work are also discussed.