Digital transformation--which goes well beyond adopting new technology--requires a comprehensive approach that addresses organizational change, strategic alignment, and employee engagement. The Region 14 Comprehensive Center (R14CC) and its partners are at the forefront of this transformation for state education agencies (SEAs). The goal is to help SEAs build the capacity to implement and sustain digital initiatives that enhance educational experiences by improving access to high-quality resources and other information essential for students' success. By combining direct support with capacity-building, R14CC ensures that state partners benefit from digital transformation and are empowered to create their own digital future. This report discusses activities that can contribute to a successful Planning and Needs Sensing phase. By engaging in these activities, SEAs can better understand their needs and set the course for a successful digital transformation.