I was reading "How Strategists Really Think: Tapping the Power of Analogy," an article from the Harvard Business Review (semi-necessary disclosure: I also have an article appearing in that magazine -- I said I've been busy!) and was struck by this comment:
Trial and error is a relatively effective way to make strategic decisions in settings so ambiguous, novel, or complex that any cognitively intensive effort is doomed to fail. In altogether new situations . . . . there may be no good substitute for trying something out and learning from experience.
Tom again: I found the article especially useful for the section on "How to avoid superficial analogies." The key step, as friend JK pointed out, is assessing the actual similarity of the two cases, or, as the authors put it, to "Actively search for differences between the source and the target."
(HT to JK)