District and school leaders are uniquely poised to serve as collaborative, innovative leaders. However, the context of current challenges often detracts from implementation efforts. This case describes how district leadership works collaboratively with school administrators through targeted efforts related to professional development, articulation strategies, and identifying challenges and opportunities. Cultivating innovation requires a realization of likely dissonance as competing priorities, such as accountability pressure or leadership turnover, can distract from planned initiatives. Realistic decision-making processes are vital in ensuring collaborative leadership and reflection while embracing change efforts.