I am pushing my brother to learn how to program: I started him with python3 hoping that he would tell me what he is interested in and move on to that.

The difficulty so far has been trying to get him to ask questions about things he doesn't understand. When something breaks it will take a 15 minute interrogation for him to simply share the actual error. I think I might be overloading him with resources that don't actually help.

Please share curriculum, collaborative tools for teaching, and anecdotes that might help out a newly initiated instructor of software construction.