Obama seems very good at that- I understand that on at least one occasion he took the Devil's Advocate position and argued against his most capable advisors to ensure that he fully understands the implications before commenting publicly. This seems in contrast to the sort of intellectually incurious statesman who forms an opinion and doesn't like to be contradicted.

Just because McCain was/is indifferent to philosophical completeness doesn't mean that Obama fully understands what he's committing to. (Check out some of his incredible gaffes in the last year when he went "off script"). Regardless of what angle Obama might argue at any one time, everything points to him trying to take this country further into a state of collectivism.