Just what were the organizers of the RSA 2008 conference on security technology thinking when they invited Malcolm Gladwell to deliver a keynote address? Had they really been taken in by the title of his bestselling book, Blink: The Power of Thinking Without Thinking, to the point that they had abandoned any critical thinking of that book's text? As a comment to Elinor Mills' account of Gladwell's talk for CNET News.com observed, Gladwell is heavy on anecdotes and distressingly light on whether or not all those anecdotes substantively add up to any lessons learned (including the one implied in the subtitle of his book). This comment highlighted the real issue behind the snake oil that Gladwell has now been pitching for several years, which is the question of what constitutes "the optimal amount of information to make sound judgment." Those who wish to dig into this question seriously would probably do well to go back to Immanuel Kant's Critique of the Power of Judgment, just to get an appreciation of the complexity of that underlying concept of "sound judgment;" but I doubt that many folks out there will pick up on this advice. Given the sort of stuff that Gladwell writes, I doubt that his attention span would last for more than a single page of any Kant source (and he is far from alone in this situation, so I really am not trying to pick on him); and I suspect that all those security professionals would be just as impatient with Kant and attack me for advising them to read old stuff when they should be concentrating on more up-to-date sources.
However, without trying to attempt a Kant for Dummies exercise, there is at least one fundamental lesson to be learned from the old guy. This is that "judgment" is almost always a matter of teasing out universal principles from specific examples. In other words Kant's Critique takes on the very problem that Gladwell cannot seem to tackle, the transition from anecdotes to lessons learned. You don't really need to read Kant to recognize that this is a problem, but it is nice to know that someone had applied so much systematic analysis to that problem over two hundred years ago!
This takes us back to the more serious question: What is this superficial claptrap doing on the agenda of a conference as serious as RSA 2008? One answer may be that the organizers decided to invite Gladwell for entertainment value, in which case my only response would be to ask if that meant they could not afford Penn & Teller. However, even where entertainment is concerned, there is a risk of trying to reduce thinking about security to anecdotes. The risk is that the result will be the same sort of deluded thinking that has led our Congress to debate questions about interrogation techniques on the basis of the pure fiction of episodes of 24; and, believe it or not, Kant has something to say about that problem, too!
It turns out that his Critique is actually in two (admittedly massive) parts. The first part is a "Critique of the Aesthetic Power of Judgment;" and it is only after he has dug into how we judge aesthetic experiences that he moves into the more practical second part, the "Critique of the Teleological Power of Judgment." The overall logic of this approach has to do with applying the model of how aesthetic experiences inform us on the more practical matters of teleological questions of cause and effect. (John Dewey was also interested in how aesthetic experiences inform us for dealing with "real world" situations; but he felt that Kant was more concerned with neat abstractions than he was with messy realities.) In other words the aesthetic experience of watching 24 (however low the aesthetic standards may be) does shape our thinking about more teleological questions, such as making decisions about interrogation or network security techniques; and, from that point of view, the satirical barbs of Penn & Teller have it over both Gladwell's grab-bag of anecdotes and the cheap melodrama of 24 hands down! If we are really concerned about the security of either the "homeland" or our computer resources, we have to "be more cynical," as Bill Maher put it and then apply that cynicism to our "teleological power of judgment." Happy reading!