[SpiralOcean]

You could try placing a "tag" in the note field that says @boss, or something unique.

Then select your top level folder
in the search field type @boss

All actions with @boss in the note will appear no matter what context.

You can then create a saved perspective with @boss in the search field.

This will give you an extra level of tagging.

Place your other actions into the appropriate contexts of what makes the most sense. Sending an email about something minor, creating an agenda for something that needs to be talked about. Waiting for actions of something you are waiting for your boss to respond to.

If you run into your boss and have some time to go over things, you can bring up the perspective that searches @boss across all contexts and go over the items.