The primary aim of institutional learning outcomes assessment is the creation of a culture of assessment where faculty use evidence-based data to validate and improve teaching and learning for the benefit of students. Faculty are key to these processes and yet, they are often woefully disengaged from them. This paper presents findings from an action research project that utilized a collaborative self-study approach to engage faculty in the strategic assessment of institutional learning (SAIL). SAIL is an immersive professional development opportunity that bridged quality assurance with meaningful improvements in the classroom. Findings indicated that cross-disciplinary dialogue about assessment increased faculty awareness of the (mis)alignment between course, program, and institutional learning aims while also identifying and informing potential gaps in curriculum and program design. SAIL is an excellent mechanism to engage faculty in an immersive assessment of student achievement that may then lead to meaningful improvement in teaching and learning.