Each year since 2003, Project Tomorrow, a global education nonprofit organization, facilitates the annual Speak Up Research Project on Digital Learning. A key aspect of the research project is to track the growth in student, educator, and parent interest in digital learning, as well as how our nation's schools and districts are addressing that interest by supporting innovative learning experiences in and out of the classroom. Since 2007, Project Tomorrow has collaborated with Blackboard to create a series of annual reports that focus on the year-to-year trends in the use of digital learning tools to change the classroom-learning paradigm through an in-depth analysis of the latest Speak Up data findings. The 2020-21 school year was a year of unprecedented challenges and difficult decisions for most education leaders. As the pandemic raged on, school and district leaders struggled with decisions about school formats, making accommodations and adjustments to meet the changing health conditions in their community and new safety mandates. To help inform critical decisions for the 2021/2022 school year and beyond, this year's digital learning trends report from Project Tomorrow® and Blackboard focuses on "Five Important Questions Every Education Leader Should Ask Today." The questions propel us to think critically about what student agency and engagement really mean for today's students. To support that critical reflection, we tap into the authentic feedback of over 50,000 K-12 students, parents, teachers, and administrators who participated in Speak Up 2020-21. This data provides research-based insights that can both clarify the needs of students and help educators see new solutions. The 5 important questions every education leader should ask today include: (1) How does technology support student learning and agency across a variety of educational settings and classroom formats?; (2) What has been the impact of remote learning and digital learning formats on students' perceptions of school and education?; (3) Are our students more or less engaged in school today?; (4) What types of learning experiences do students want and prefer?; and (5) What can your school or district do to meet the needs, expectations, and aspirations of students for a more equitable and engaging learning experience?