That requires some sort of feedback regarding what I looked at in the past, and what sources of meaning each user is most comfortable with. You're right about the Big Brother aspect of intense monitoring. However, my tendency to look at cartoon boxes first and often is a signal to the system to send knowledge to me in the form of cartoon boxes in the future. Others might rather have that same knowledge communicated to them by a coworker, because that is the source they pay attention to and gain clear meaning from. It does not know a thing, but it is less apt to filter as much as a human does.
Humans tend to turn to certain sources again and again, and ignore or forget others.
The system does not know what the user needs. Not at all. That is only what is put in front of you automatically. But you raise a nice point of also including random knowledge, in user friendly context and form. In my fictional creation, I receive information pertaining to what happened today, yesterday, and ten years ago.