11/25/2013 02:34 pm ET Updated Jan 25, 2014

The REAL Problem With the Obamacare Roll Out: A Teachable Moment for our 'Instructor-in-Chief'

Admit it.

It wasn't surprising to hear that only about 26,000 people had successfully signed up for insurance via during its first week online. What's surprising is that the media is still focusing on the wonky Web site.

Truth be told, some basic but crucial steps were skipped long before the debacle. Let's look closer.

Remembering JFK last Friday in Dallas, historian David McCullough said, "He spoke to the point and with confidence. His words changed lives, changed history."

Kennedy rocked that "Bully Pulpit" we hear so much about. The most popular and oft-quoted presidents have all used it meticulously, stating and repeating the ideas for which they are remembered and revered as eloquently and as often as possible.

Good teachers do that, too. Back when I was a teacher, we were trained to repeat important concepts at least five times both during both the lesson and the week that followed to make sure they were safely stored in all those hormone-addled teenage brains. If you have a loved one who teaches, you've probably seen that technique in full effect outside the classroom, too.

Forgive us. Those old habits die hard.

But it's a habit Obama, our "Instructor-In-Chief," really needs to develop. It's his Achilles heel, this failure to communicate at crucial moments.

And that's a shame. Because correctly sold, the Affordable Care Act might have swept through Congress on a tidal wave of public support. Correctly sold, it also might have motivated millions to hang in there despite the weird Web glitches.

Remember when Clinton ran the party platform down for us during that amazing Democratic Convention speech that Obama probably should have made himself?

He made each point crystal clear, skillfully building to the "coup de grace" and offering "sound bite ready" slogans for the audience to repeat and remember. That's teaching at its best.

So speaking of's a pop quiz:

1. When did you first find out there was a Web site where you could get information about "Obamacare?"
2. Where did you get the URL for the Web site?
3. Do you know the deadline for submitting an application?
4. Did you know there was a deadline for submitting an application?
5. Do you know if you need to submit an application?
6. Do you understand why I'm asking you these questions?

If you answered "Yes" to question six... forget the other five. You know I asked because if you took a little straw poll in your very own neighborhood using those questions today, you'd get a lot of blank stares and "hemming and hawing."

And if you did same in the neighborhoods that need Obamacare most... it might make you weep.

So the most embarrassing thing about Obamacare's debut isn't that didn't work. It's that millions of potential "customers" were unaware that it even existed.

Given how hard Obama fought to pass this law, I expected an endless stream of speeches and articles and commercials and radio ads and magazine ads and newspaper ads and emails and snail mail and local volunteers going door to door to give us the skinny on Obamacare.

Never happened. And I just cannot understand why.

Anyone in a position of power, from CEOs to school administrators, can tell you that big changes require lots of front loading. That helps create "buy in," that elusive but priceless thing all leaders must have to get things done.

To create that buy in, the president could have given a series of "lectures" about the Affordable Care Act before and after it was passed. During the months leading up to the debut of, there should've been a deluge of print and radio ads -- maybe even some of those hokey public service TV commercials with two "regular guys" out mowing the lawn and saying things like:

"Hey, Bob! What's this Affordable Care Act thing I've been hearing about?"

"Wow, Dave! It's a good thing you asked! It could save you enough money to buy yourself a real lawn mower! Haw, haw, haw..."

Would people get tired of it? Yep. But as we're so often told, P.T. Barnum believed there was no such thing as bad publicity. In fact, there's an apocryphal story about how he spat on a table and told the grimacing onlookers that even if they were disgusted, they would never forget him. Or that mental image.

That wasn't necessarily good teaching. But it beats the dearth of any type of truly effective instruction we got before went live. I get an email from Obama asking me for a $3 donation almost every day. Why couldn't they send out a few more telling folks how to save some money on health care so that they could actually make a donation from time to time?

One more quick teacher tip -- no, two. First, always test drive that DVD player, tablet, Smartboard, Web site -- whatever the students will need to get the job done. Murphy's Law is no joke.

Second, try to anticipate student questions, both technological and...potentially inappropriate. Those snarky student questions can end a lesson as surely as a power outage. That's why all good teachers have back up -- and "comebacks" -- ready.

Obama, on the other hand, seemed totally unprepared. Big red "F" for this one, Mr. President.

Educators call 'em "teachable moments," big bloopers like these. Here's hoping Obama has learned something from this one.

Because rest assured there will be a test on this -- a test just like this, in fact -- later.

Cynthia Dagnal-Myron's book of essays, The Keka Collection, can be purchased on