The article investigates the impact of assessment data analysis on promoting deeper learning in Canadian high schools, specifically focusing on teachers’ flexibility in data-driven evaluation. The research contributes to the discourse on assessment practices by emphasizing the importance of authentic assessments, competency-based learning, and grading methodologies. Selected high school teachers drawn into this further study formed a fraction of the initial set of participants. Classroom practices of assessments concentrate on: (a) Freedom to facilitate deeper learning in instructing, assessing, and sustaining interest. The others are: (b) Teacher’s emphasis on competency-based (standard-based) learning to make learning appealing to students in educational spaces, and (c) Testing, collecting test score data, analyzing, and reporting students grades to present parents and school districts/boards with accurate progressive data reflective of diversity in learning. In this qualitative focus group case-study discussion, participants indicated time expended in performing critical analysis of data to grade students is burdensome, but the joy of such practice far outweighs the inherent difficulties, knowing that student success is founded on flexibility, freedom in decision-making, and being reflective as educators.