The application of skills and knowledge to a "real world" context entails a greater set of competencies than just technical proficiency, for both the student who sits the problem and the teacher who sets it. These competencies require unpacking. A greater understanding of these competencies would enable teachers to create tasks that test what they are supposed to, with improved insight into difficulty level. Moreover, it would enable students to receive not only a better training for those tasks, but also a more meaningful education. The reflections presented in this article are an attempt to begin this unpacking process and are based on the teaching experiences of the author.