[Brian]

Happy to help, but my initial suggestion sounds like something you've tried and decided not to do. Specifically, assign the questions for each person to a context created for that person. So in your "Brad" example, you'd have one or more items assigned to them, probably with the customer names captured in the action title.

Each action would be a specific topic you needed to address. (Example action title: "Get status update on Acme project".)

Oh, wait, I think I'm beginning to see what's going on here - during a phone call with Brad, you want each and every project they're working on to appear? Is that right? If so, my first recommendation would be to reconsider that.

In my mind, it's better to be able to click on Brad's context and just see the actions (from any number of projects) that you needed to consult with him on. Trying to show the entirety of every project he's working on is going to get overwhelming really fast - you're going to be seeing a bunch of actions assigned to other people, for example.

If I'm not understanding what you're trying to do, describe things a bit more and we'll be happy to help.

(Side note: I personally don't find Waiting For contexts useful in my workflow. Instead, I just have a single context per person and use the Start Date field to defer actions temporarily until I want to check back in on them. YMMV.)