For President Obama, the one “must read” from the latest Sunday papers is an essay in The Post by Jon Kingsdale, who ran the health exchange for the Massachusetts program of mandatory insurance from 2006 until 2010. Kingsdale — a backer of the Affordable Care Act, or “Obamacare” — thinks the administration faces lots more problems, even if the Web site eventually gets up and running.

Kingsdale says that in Massachusetts, a reliable Web site was only a modest worry. (Disclosure: Kingsdale and I once worked for the same employer and knew each other. But we haven’t spoken for many years.) Much harder was getting “enrollment, billing and premium collections working smoothly.” Here’s why:

“Enrollees are not covered until their first month’s premium is received. In the individual insurance market, premium billing and collection [are] difficult to track. Folks frequently pay late or in weekly installments, or send too little or even too much. And when they stop paying, they often do not notify the insurer; the company must determine whether it is an intentional termination, an oversight, or a lost or late payment. . . . If insurers cannot track and collect premium dollars each month, the extra work of doubling back with customers and insurers will frustrate consumers and delay coverage. And a mounting backlog could eventually compromise the fiscal integrity of the exchange.”

Translation: Assuming the Web site is completely fixed, Obamacare’s woes could still slow its introduction or, at worst, result in its collapse.

One danger for the administration, Kingsdale says, is much higher premiums. If people are frustrated in signing up or staying signed up — especially among so-called “young invincibles” whose premiums are supposed to subsidize older, sicker people — then insurance companies will raise premiums to cover costlier enrollees. Higher premiums for 2015 (most rates are set for 2014) will become public next fall, just weeks before congressional elections, Kingsdale notes. Obama’s greatest legislative triumph could backfire big time.

Without intending it, Kingsdale has, I think, identified a central source of Obamacare’s problems: The people who created the program had no idea how it would be put into effect. They just took it for granted that the law would be implemented and perform, more or less, as intended. This attitude blended carelessness, ignorance and arrogance, reflecting a broader problem in business and government.

There’s a class structure to huge public and private organizations. One class — usually the leaders of enterprises or departments — might be called the Pontificators. They enunciate broad, often-worthy goals and values. President Obama (indeed, almost any president) ranks as the Pontificator in Chief. In politics, elected officials and pundits (people like me) are lower down on the Pontificator scale. In business, these people cluster in the executive suites.

But most workers belong to the Plumber class. They’re the fix-it folks. They’re supposed to put the Pontificators’ pronouncements and commands into effect. Never mind that these demands are often impractical, inconsistent or uninformed because the Pontificators have only a sketchy notion of what the Plumbers do or what the real world requires.

Writes Kingsdale of Obamacare:

“A health insurance exchange is more than a Web site. It is an insurance store, and to manage it well requires insurance experience, technical know-how, and savvy marketing and sales tactics.”

Precisely. Whether the administration recognizes this and still has the time to act on it are crucial and open questions.

Read more from Robert Samuelson’s archive.