How would you approach creating a negative message for a superior (such as a menager at work or an instructor) versus creating a message for a colleague, subordinate, or fellow student.

The basic difference to me is that you cant afford to tell a manager at work that she is the problem, and needs to shape up, whereas you might get by with telling that to a peer...but in both cases, it is best to couch a negative in positive light. After all, people have egos that need to be admired and stroked.