There are variations on this for other issues, but the question I would ask would be, "If in response to an international crisis, you received memos from an interventionist and from a realist, what criteria would you use to evaluate whose advice to follow?"
To see the impact of such a question, consider the Arab Spring in Egypt and Obama's decision to force Mubarak to step down. If the question of whether or not to support Mubarak was posed as whether or not to support him to the bitter end, then a reasonable case could be made that doing so would carry costs that are not worth paying. At that point, the question becomes one of at what point do we throw in the towel. With that type of formulation, there is no right or wrong answer, so whatever condition is selected to concede Mubarak's loss would be reasonable.
Initially, I thought that Obama's reasoning process followed such a path. However, Robert Gates recent revealed (h/t Ian and EoZ) that such was not the case. Instead, all of the senior defense officials recommended caution in responding to events then unfolding in Egypt while three junior "back-benchers" said that it was Obama's responsibility to be on the "right side of history." As we know, Obama selected the advice from those three back-benchers.
The problem with arguments to being on the right side of history is that doing so also carries the responsibility of thinking through what happens the day after the ancien regime is overthrown. Part of doing so is assessing whether the most likely successor would resemble more Thomas Jefferson or Maximillian Robespierre. Since Obama did not ask those questions, a potential disaster was set in motion as the Muslim Brotherhood came to power, fortunately to be mitigated by the army ousting the Brotherhood in a coup.
The question I pose might have illuminated Obama's thought process in 2008, possibly exposing his susceptibility to arguments like "the right side of history."