I love your context report in place of a status report. There is always a but with this kind of thing, the but in this case is that most workers just don’t write that well.

Part of the manager’s job is to design reporting processes that their employees can actually use without investing so much time that it impacts their regular job. For most team leads and first line managers writing the kind of descriptive text you do is beyond their experience and training.

Your context based tracking will only work effectively if the senior manager is willing to invest the time and effort to train his direct reports in what is important and how to report it. The burden is always on the senior manager to clearly define and explain what she/he wants and to allow the subordinate time to get it done.