This article addresses the challenge of personalizing learning while also ensuring alignment with system and school improvement plans. Leaders of the York Region District School Board in Ontario knew that what took their high-performing school district from good to great would not take it from great to excellent. The district's early model of improvement, centered around prescribed diagnostic assessment and prescriptive professional learning, did not ensure ownership from teachers, nor did it value the voices of students, teachers, and other stakeholders. Moreover, with increased access to social media and online professional learning tools, staff members were finding their own ways to learn. In a section titled "Focus on Collaboration and Inquiry," school principal, Debbie Donsky, describes how her school's leadership team meets to talk about what has gone well, what has been challenging, and where growth needs to occur. Superintendent of curriculum and instructional services, Kathy Witherow, discusses the need to re-examine not just what is being learned, but also how, when, and where learning occurs in a section titled "Alignment and Coherence Are Key."