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(CNN) -- Irony is a part of life, the cliché goes. And right now, President Barack Obama is living the part, in a big way: He's the civil libertarian defending an activist drone program. He's the liberal with a spy agency caught eavesdropping on the private conversations of friendly leaders. And he's the high-tech health care reformer whose website got stuck at Go.

And so the ultimate irony may be this -- a President who extols the virtues of government has now been sucked into the big government vortex, experiencing (up close and personal, as they say) what it feels like to lose control to the bureaucrats. The ones who are afraid to deliver bad news, not to mention those who don't deliver the news at all. (As in, "the website crashed.") And the surveillance chiefs who, um, didn't initially volunteer that they're spying on the private phone lines of America's best friends.

Maybe the President needs to figure out some new communications tools to make himself clear. (As in, "Angela Merkel's cell is not just another data point.")

Obama, we're told, is frustrated and angered by the pathetic rollout of his signature legislative achievement. He's also clearly re-examining how the National Security Agency decides to target friendly leaders, what we get from it and why we need it at all.

A couple of ex-intelligence officials tell me they're not shocked gambling was going on in Casablanca. ("Our job is to know things," says one.) Whether the President should have known about the monitoring of these specific heads of state is another matter entirely -- and best left to intelligence aficionados. I've asked -- and gotten answers on both sides of the argument.

But here are the larger questions that play into both the website fiasco and the NSA issues: How can a President take control of his own government? How can he make sure he knows what he needs to know? And as the pro-government cheerleader, doesn't he have a special responsibility to make sure it delivers, especially when his legacy hangs in the balance?

The problem is it's never easy to untangle a bureaucratic mess. "So you're the President, you're angry and you want to know how all of this happened," says a former senior administration official. "And the truth is, even you may not be able to figure it out. You just won't have enough time left in office."

Stunning as that sounds, it's probably accurate. Presidents are often isolated, and always the first among equals. So it seems to me that especially in the White House one of the principal jobs of an executive is to understand the incentive subordinates have to conceal information selectively.

People may report facts and then spin them. Bad news is not a good thing to deliver to presidents. Some are protective of the office and the President; giving the President plausible deniability of any problem is often the easiest and safest route. Or, as one former White House hand told me, "People just don't want to upset the boss, or get him blamed for anything."

All of which a President should know going into the Oval Office. If the reason the President did not know about the epic website issues is because the problems were hidden from the ground up, how about this solution: Establish an atmosphere, at all levels, in which truth telling is rewarded, not punished.

If Obama was surprised at the rollout of the Affordable Care Act, then on some level he failed one of the principal tests: Get the truth out of people, even if they know you are not going to like it.

Yes, this is government and humans are humans. But Obamacare has been the signature legislative achievement of this presidency. Everyone knew how complex this would be to get going, at every level.

So here's a question: Why wasn't the A-team led out of the White House, with a daily update to the president? Obama the campaigner was incomparably good at establishing metrics and using information technology to assess the extent to which those metrics were being hit. What happened here?

What seems to have happened was what often happens: The work got delegated to the bureaucrats somewhere else -- HHS? CMS? -- and, as a result, it got bogged down, delayed and muddled. Mistakes went either hidden or unrecognized. If folks down the food chain knew, they were keeping it from their bosses. After all, no reward in telling the truth.

The big question now is whether these problems are evidence of a huge management failure. "One of the things you find after working in government is that, under tremendous pressure, organizations that are supposed to produce accurate information, often don't," says a former senior administration official (think Benghazi). "And you can only rely on what people are telling you."

Or not telling you, as in the case of Merkel's cell phone. If the President and senior officials were not told about the wide range of the program, who thought that secrecy was a good idea?

Does a President have to play a game of Twenty Questions with his own people to figure things out? Or, conversely, as some intelligence officials claim, if the President did know something -- some giblet -- why not more? It's not as if Obama is a passive examiner of intelligence; quite the contrary. So what gives here?

Consider this: You're President Obama. You believe in the affirmative use of government. You're trying to govern a country that has lost confidence in the ability of that government to execute anything. And now you discover the website of your prized legislative achievement is a disaster. And the spies were tapping a good ally's cell phone, for no immediately obvious reason.

The final irony may be this: Four out of five Americans have little or no trust in their government to do anything right. And now Obama probably feels the same way.

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The opinions expressed in this commentary are solely those of Gloria Borger.