[keone]

I view my contexts more in terms of how or where I will be communicating with others. In other words, to use your example of your boss Andrew, I would ask myself how I will communicate on a particular issue with him: By phone? In person? Or via email? Then that becomes my context for that action. Re: my in-person contacts I have a PEOPLE context with sub-contexts of the names of those with whom I communicate on a regular basis.

As for waiting fors, here's how I handle them:

Let's say that I have an action with a "Phone" context. I make that phone call on the prescribed date, but now need to wait for something back from the person I called in order to move the project forward. I briefly write down a summary of the call in the note section under that "Phone" action, and then change the context to "Waiting For" with a due date of, say, three days out, changing the action to something like this: "WF c/b from Joe." (Translation: Waiting For a callback from Joe.) Now, three days later when I'm in context view I can readily see that a red badge next to my "Waiting For" context indicates that I have one item due. I click on the "Waiting For" context, and there it is, a recap of that phone call of three days ago. Since I haven't yet received whatever it was I was waiting for, I now have three choices: a) Call that person to follow-up; b) Bump the due date forward another two or three days (or as Curt suggested use both a start and due date so I don't see it until I need to); or c) Ignore it and let the action sit there in red until I do something with it.