A pledge by all parties not to learn anything while doing the actual work

Two articles that are interesting to read as a pair. Both Clay Shirky and Peter Berkowitz are almost always interesting and insightful The first article, by Shirky is a rumination on the Healthcare.gov failure, not as a failed information systems project per se (though it is a fairly spectacular example of that), but rather as an epistemological failure which I believe is really at the core of the issue. And the epistemological model is in part a failure of culture.

Very early in Obama's first term, there was a desire on the part of the Administration to close Guantanamo and bring the terrorists held there to the US for civil trial. There was quite a kerfuffle when it came time to consider a civilian trial for Khalid Sheikh Mohammad. In the hearings to review this plan, the Attorney General Eric Holder had the following profoundly revealing exchange with Senator Herbert Kohl, Democrat, Wisconsin.

Kohl: Mr. Holder, last week you announced that the department will bring to Guantanamo [sic in transcript] detainees accused of planning the 9/11 attacks to trial in federal court in New York, as we've talked about this morning. On Friday you said that you'd not have authorized prosecution if you were not confident that the outcome would be successful. However, many critics have offered their own predictions about how such a trial might well play out.

One concern we have heard from critics of your decision is that the defendants could get off on legal technicalities, in which case these terrorists would walk free. Does this scenario have any merit? If not, why? And in the worst case scenario that the trial does not result in a conviction, what would be your next steps?

Holder: Many of those who have criticized the decision--and not all--but many of those who have criticized the decision have done so, I think, from a position of ignorance. They have not had access to the materials that I have had access to.

They've not had a chance to look at the facts, look at the applicable laws and make the determination as to what our chances of success are. I would not have put these cases in Article III courts if I did not think our chances of success were not good--in fact, if I didn't think our chances of success were enhanced by bringing the cases there. My expectation is that these capable prosecutors from the Justice Department will be successful in the prosecution of these cases.

Kohl: But taking into account that you never know what happens when you walk into a court of law, in the event that for whatever reason they do not get convicted, what would be your next step? I'm sure you must have talked about it.

Holder: What I told the prosecutors and what I will tell you and what I spoke to them about is that failure is not an option. Failure is not an option. This--these are cases that have to be won. I don't expect that we will have a contrary result.

I found this profoundly shocking from two perspectives. Either what the AG said was true and that failure would not be countenanced, in which case this was simply a show trial. He wasn't arguing that failure was unlikely, he was arguing that it couldn't happen at all.

Alternatively, the most senior lawyer in the land truly believed that there was simply no way that an unbiased and fair jury trial could render anything other than a guilty verdict. A belief that could not possibly be grounded in experience or reality.

The distress was the realization that our AG was either corrupt (rigged trial) or stupid (mistaking desire for reality). It seemed that there were few alternative interpretations. But perhaps it was simply a flawed epistemological model founded on a faulty culture. Read Shirky's whole post to see the parallels with the Healthcare.gov failure.

From Healthcare.gov and the Gulf Between Planning and Reality by Clay Shirky

The idea that “failure is not an option” is a fantasy version of how non-engineers should motivate engineers. That sentiment was invented by a screenwriter, riffing on an after-the-fact observation about Apollo 13; no one said it at the time. (If you ever say it, wash your mouth out with soap. If anyone ever says it to you, run.) Even NASA’s vaunted moonshot, so often referred to as the best of government innovation, tested with dozens of unmanned missions first, several of which failed outright.

Failure is always an option. Engineers work as hard as they do because they understand the risk of failure. And for anything it might have meant in its screenplay version, here that sentiment means the opposite; the unnamed executives were saying “Addressing the possibility of failure is not an option.”

The management question, when trying anything new, is “When does reality trump planning?” For the officials overseeing Healthcare.gov, the preferred answer was “Never.” Every time there was a chance to create some sort of public experimentation, or even just some clarity about its methods and goals, the imperative was to avoid giving the opposition anything to criticize.

[snip]

This is not just a hiring problem, or a procurement problem. This is a management problem, and a cultural problem. The preferred method for implementing large technology projects in Washington is to write the plans up front, break them into increasingly detailed specifications, then build what the specifications call for. It’s often called the waterfall method, because on a timeline the project cascades from planning, at the top left of the chart, down to implementation, on the bottom right.

Like all organizational models, waterfall is mainly a theory of collaboration. By putting the most serious planning at the beginning, with subsequent work derived from the plan, the waterfall method amounts to a pledge by all parties not to learn anything while doing the actual work. Instead, waterfall insists that the participants will understand best how things should work before accumulating any real-world experience, and that planners will always know more than workers.

This is a perfect fit for a culture that communicates in the deontic language of legislation. It is also a dreadful way to make new technology. If there is no room for learning by doing, early mistakes will resist correction. If the people with real technical knowledge can’t deliver bad news up the chain, potential failures get embedded rather than uprooted as the work goes on.

Now read Peter Berkowitz's Obama's Slow Learning Curve.

But perhaps the president’s most astonishing statement involved an insouciant confession of ignorance. Returning to a common but under-appreciated motif of his presidency, Obama remarked: “What we’re also discovering is that insurance is complicated to buy.”

What deficiency of Obama’s education and of the education of those who surround him accounts for administration officials not knowing what is perfectly well-known to most ordinary Americans?

This discovery that purchasing health insurance is complex is just the most recent of the rather stunning lessons that Obama professes to have learned on the job about how the world really works.

Berkowitz then goes on to list and discuss additional things that Obama ended up acknowledging not knowing what he was talking about; Peace between Palestine and Israel - “I think that we overestimated our ability to persuade them to do so when their politics ran contrary to that"; the 2008 stimulus program - “shovel-ready was not as shovel-ready as we expected"; the implementation of the Affordable Care Act - “Now, let's face it, a lot of us didn't realize that passing the law was the easy part.”

Contrary to the president’s breezy attitude suggesting that these drastic miscalculations were not knowable in advance, we know that all were foreseeable because all were perspicaciously foreseen by critics from the beginning. (The only possible exception is the staggeringly inept rollout of the HealthCare.gov website, the magnitude of which caught even the president’s toughest critics off guard.)

It’s a cliché that democracy is messy and difficult; it’s a truism that politics demands the cutting of deals and the hammering out of trade-offs; it’s common knowledge that implementing public policy and conducting diplomacy involve unforeseen obstacles and intricate maneuvering that are hard to grasp from the outside.

Yet all this keeps catching Obama and his aides by surprise. Team Obama’s surprise, however, is really not all that surprising.

Berkowitz's explanation for serial disengagement from reality?

The president and the officials around him are the product of the same progressive version of higher education that simultaneously excises politics from the study of government and public policy while politicizing education. This higher education denigrates experience; exalts rational administration; reveres abstract moral reasoning; confidently counts on the mainstream press to play for the progressive political team; accords to words fabulous abilities to remake reality; and believes itself to speak for the people while haughtily despising their way of life.

The education President Obama received at Columbia University and Harvard Law School -- and delivered to others as a lecturer at the University of Chicago Law School -- encourages the fantasy of a political world subject to almost limitless manipulation by clever and well-orchestrated images. This explains why the harsh exigencies and intractable forces of politics keep stunning the president, each new time as if it were the very first.

Is Berkowitz right? Probably in part. Our best universities do serve as an effective sorting mechanism. You know where to go to find the brightest candidates. But they are not always the most effective or the best. The best of them are able to acquire truly phenomenal educations. But many, regrettably, end up wandering into academic la la land from whence few are known to return with any desirable capabilities and many distorting beliefs.

The infusion of post modernism, critical race theory, gender studies, etc. have put large swaths of reality beyond critical discussion to the great detriment of all. More spectacularly they have created an environment in which the fervor of belief is allowed to supersede logic and evidence. It is a somewhat ironical turn of fate that segments of the academy are the ones so married to an entirely faith-based postmodernist secular creed whose foundations are patently separated from reality. Is it any wonder that the products of such education can find themselves in such deep water when their fervid belief that failure is not an option turns out to be founded on quicksand.

Reality is a cruel mistress to the post modernist faithful.