Unforseen

Ask him to skim "Seeking Alpha" or some other source (IBD, Barron's, etc.) and identify what he thinks are 5 relevant articles for you and what you do.

Have him write a one paragraph summary of what the argument is and why it might be relevant to what you do. This is as much to focus his mind as to give you a brief you can use.

Then have a chat with him about what the articles are and why he chose them. If he picks good stuff, give him that feedback and ask him to do more or dig deeper; if he picks irrelevant stuff, explain to him why it isn't as relevant as it sounds, and what kinds of stuff would be more helpful.

The goal would be to have him help you identify good ideas for your work and learn how to find them for you.