And I think success in engineering school is about learning how to solve a problem where the method is given and the result is unknown. In my experience, in practice engineering is knowing the answer and then figuring out how various methods prove (or just as often disprove) that answer. I've tried this, and "unimaginative" is a good description. I had one success on Monday with "(blank) didn't have any effect" (which was the correct observation). Then today when trying to coax him into an observation he went back to "I could try (blank)." I'll have to think about why that didn't work.Sometimes you can get the unimaginative to grasp the issues of the boundless story problem by getting them to find the bounds.
Yep, it seems like most things go the road of "well, x is what I want/needs to happen given our current equipment/business processes, but y is what is currently happening. How do I get to x?" What about something along the lines of asking him to come up with multiple possible solutions, and then asking him to rank them with reasoning? Kind of promotes more typical problem solving and might indirectly lead him into the wonderful world of some basic principles of risk and project management.