Both "teaching" and "teaching" with Geographic Information Systems (GIS) are "wicked problems," in the sense that they involve multiple variables that interact with one another. Effective teaching calls for both learning with understanding and transfer. The authors' own experience implementing a geography and geospatial inquiry project with middle school students gave them the opportunity to wrestle with the challenges of using GIS in the classroom. This unit posed a driving problem to the students regarding water drainage in the neighborhood. Students first conducted a field survey of storm drains in the neighborhood. The data was loaded into ArcExplorer-Java Edition for Education (AEJEE) for analysis and pattern-recognition, and the unit culminated with a transfer task of planning the locations of storm drains for an adjacent neighborhood. After three successive rounds of instruction and assessments with multiple classes (totaling approximately 200 students), they have identified several strategies for enhancing student understanding and reducing technical friction (and frustration!) in working with AEJEE and other GIS designed for use in school settings. Each of the strategies the authors developed address two critical questions that students face when working with GIS: "What am I looking at?" and "What am I trying to do?" Accordingly, they have grouped the strategies under these two questions. Their intent, at every step, is to lighten the cognitive load of students and gradually engage them in the process of using a GIS and conducting an inquiry. (Contains 3 figures and 7 notes.)