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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.