This Occasional Paper outlines lessons learned about mapping and assessing learning in student affairs and student employment. Over the last three years, the National Institute for Learning Outcomes Assessment (NILOA) assisted institutions developing Comprehensive Learner Records and scaling high-impact practices. In each of these initiatives, mapping of learning, redesigning assessments, and creating assignments was a staple of practice. Further, assessment practitioners were reminded that before staff jump into implementing assessment and writing the perfect learning outcome statement with just the right verb, time is needed to think about what is being built, why, how, and which students are best served by it all. The discussion centered upon: What is the role of student affairs as part of a larger system of interlocking and supporting learning for students throughout an institution that builds towards common or shared learning outcomes? This resource provides inroads to such discussions, and offers resources to inform practice and for use in institutional professional development.