How is it possible that Barack Obama did not know that his beloved healthcare.gov website was a botch? That’s a question many thoughtful people (including thoughtful Democrats) are asking.

We heard him say that he wouldn’t have boasted that it would be as easy to use as amazon.com or obitz.com had he known that it wouldn’t. I’m not “stupid enough,” he said at his Nov. 14 press conference. Most Americans agree that’s true.

One thing we do know is that this is a chief executive who does not want to hear bad news, or at least effectively discourages his subordinates from bringing it to him.

He made a decision to take the question of intervention in Syria to Congress after consulting, on a walk in the White House lawn, with his chief of staff. Any staffer with knowledge of congressional opinion on the issue could have told him that he didn’t come close to having the votes.

And it’s known that his White House counsel, Kathryn Ruemmler, learned the week of April 22 from Treasury lawyers that the Internal Revenue Service had, in her words, “improperly scrutinized several … organizations by using words like ‘Tea Party’ and ‘patriot.’”

Evidently, she didn’t tell the president, who said he learned about the scandal only when it was made public by IRS official Lois Lerner May 10. Counsels to former presidents of both parties say they would have informed their bosses immediately.

Effective executives take special pains to ferret out bad news from the organizations they command. They know that most underlings like to tell their superiors that things are going fine.

“A culture that prefers deluding the boss over delivering bad news isn’t well equipped to try new things,” writes Internet pioneer Clay Shirky on his eponymous blog. As Shirky explains, in developing software there is a “a tradeoff between features, quality and time.”

“If you want certain features at a certain level of quality, you’d better be able to move the deadline,” he writes. “If you want overall quality by a certain deadline, you’d better be able to simply delay or drop features. And if you have a fixed feature list and deadline, quality will suffer.”

You find out what works by testing, “even if that means contradicting management’s deeply held assumptions and goals.” But the testing of the Obamacare website was, he says, “late and desultory.”

Government doesn’t have to work this badly. The Obama administration had 42 months from the passage of Obamacare to the scheduled rollout of healthcare.gov. The Pentagon, still the world’s largest office building after more than 70 years, was built in 18 months.

But that was accomplished by men who knew that the Commander-in-Chief, Franklin Roosevelt, expected results. Roosevelt could be an inspiring orator. But he also showed a gift for selecting the right men (and, occasionally, women) to reach goals that he thought were really important.

Barack Obama seems to lack that knack. He has advanced to the highest position in government without having demonstrated the ability to get results outside a political campaign.

He is the product, as the Hoover Institution’s Peter Berkowitz writes, “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,” Berkowitz continues, “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.”

Or to put it more pithily, Obama knows how to use words well. But he doesn’t seem to understand how the world works. “We’re also discovering,” he said at that press conference, “that insurance is complicated to buy.” Yup.

There is a reason public policy in industrial age America (and other democratic countries) moved toward greater regimentation and standardization. Centralized command and control was a good way to run assembly lines.

There is a reason also that public policy in the information age, elsewhere and here until 2008, moved toward more market mechanisms. Central planners have a hard time anticipating how IT systems and consumers will respond.

That’s especially true when chief executive doesn’t want to hear – and perhaps cannot imagine that there will be – bad news. Welcome to the kludgeocracy.

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