The lesson from Healthcare.gov? Time for you to become a geek

"All of that is well and good, but if the Web site doesn't work, nothing else matters." —President Obama

According to the Washington Post, “No matter which aspects of the sprawling law had been that day’s focus…Obama invariably ended the meeting” with the above quote.

Yet, how did a man who understood the grave importance of Healthcare.gov let it go so horribly awry? In the answer to this question lies an important leadership lesson: It’s time to become a geek.

HealthCare.gov lacked geeks

Very few of the leaders in charge of overseeing the building of Healthcare.gov actually understood how to build technology.

They understood the importance of technology. But they did not understand how to build technology. And that lack of intuitive understanding and respect for the nature of how technology is built led to decisions that doomed the project's launch.

None of these people wanted to land in this position. They were all perfectly well intentioned. Yet here they are.

Here is how you avoid their fate.

Your CEO wants geeks

The first step is to reframe how you view yourself. In meetings regarding technology, I’ve noticed a lot of leaders will go out of their way to make clear that they’re “not a techie.” And I get it. Not a bad idea to point out a gap in knowledge so people don't mistake you for an expert. But here's the bad news: Not being a techie makes you increasingly disposable.

In fact, IBM aggregates a list of the external factors that CEOs think will have the biggest impact on their organizations. Between 2004 and 2010, technology jumped from sixth place to second.

Saying you're not a techie is like telling your CEO that you don't have people skills (which, by the way, is fourth on the list, two notches below technology). It’s time to come to terms with the fact that being a geek is a core competency, just like people skills. Everyone has to become a geek.

What does it mean to be a geek?

Strategy is a high level plan to achieve one or more goals under conditions of uncertainty. (Source: http://en.wikipedia.or/wiki/Strategy)

At its core, being a geek means rejecting qualities that many of us have aspired to develop during the course of our careers. There was a time when a lot of respect was given to strategy. When I started work as a consultant at Towers Watson, the greatest compliment one could pay to a client was to say they were “strategic.”

But, by definition, strategy is quite ambiguous. With strategy projects, you can use political blocking and tackling to make a project look successful without doing its job at all. The Obama team seemed particularly adept at that part of the job — and many corporate managers are too.

To be a geek is to reject “strategic thinking.” The geek realizes that in a fast-paced environment, focusing on strategy alone is self-defeating. The geek seeks glory in quantifiable learning through doing. Quantifiable learning means real results.

A geek understands that technology rejects ambiguity. That simple things can be very hard and hard things very simple. That the best way to figure out the difference between the two is to learn through doing.

Rule No. 1: Technology does not understand ambiguity

When you talk to a programmer, you'll notice they're very deliberate with their use of words. They're trained that way because the exact words they use when they write a program must be understood by a computer. The computer does not understand “maybe.” Incompetence and indecision cannot hide in a cloud of strategy and ambiguity.

No amount of political campaigning that Department of Health and Human Services Secretary Kathleen Sebelius did before the launch of the site changed the fundamental fact that the site didn't work. Lobbying does not persuade a computer program very much.

Technology is unforgiving. It rewards hands-on leadership. It punishes aloof leaders with failure.

Rule No. 2: Things that look easy are hard

The technological undertaking behind healthcare.gov is breathtaking. The lack of respect the Obama administration gave that fact is equally breathtaking. The evidence of this is everywhere, but especially so in the fact that the administration was still changing specs on the system months before launch.

To give you an idea of how ridiculous this is, let's take a look at a relatively simple service, Twitter — a service that is almost entirely based on typing 140 characters into a box, and then sharing those 140 characters. In reality, its complexity is so surprising, that Bloomberg Businessweek made the subject its cover.

Technology is more complex than anyone gives it credit for. Even simple things can be very hard. But it’s difficult to know how hard or easy something is until you get your hands dirty, which leads us to rule No. 3.

Rule No. 3: Get hands-on

To understand technology, you actually have to get hands-on. You need to develop an intuitive sense of what’s possible, in what time frame and with what quantity of resources.

If Obama had taken an HTML course on Codecademy, he would have understood how ridiculous it is to build such a complex system while changing requirements. It’s like asking someone to do something, and then changing the instructions when they’re almost done.

If he had talked to a programmer or two, he would have understood that double the resources does not mean double the speed. Or, as Fred Brooks, a project manager for IBM in the 1960s put it, “adding manpower to a late software project makes it later.” So it’s not like you can make up for changing instructions by working twice as hard — in fact, this will most likely make the situation worse.

Obama may have even understood that deploying a new technology is more like introducing a foreign species into an ecosystem: It’s almost impossible to model all of the ways that the organism (technology) will interact with its environment (users) until it happens. That’s why a staged rollout, and plenty of testing — the exact opposite of what healthcare.gov did — is so crucial for success.

Commander in Geek

I believe that if he’d understood all of this, Obama would have become the Commander in Geek that some of us hoped he would be. Obama would have reverse-engineered the political conditions that needed to exist in order to make a successful technology implementation possible. Because, as the man himself said, "[I]f the Web site doesn’t work, nothing else matters.” It’s just unfortunate he lacked the practical wisdom to make that statement meaningful.

At this point, it’s worth pointing out two things.

One, I don’t identify myself with either Democrats or Republicans. This isn’t an anti-Obama article. I actually admire him quite a bit.

Two, many people reading this post will not take it seriously. So you have a competitive advantage if you do. And here are two things you can do right now:

Take a course on codecademy.com; it’s free. Start with HTML and CSS. HTML is the computer language that Web pages are made of, and CSS is another language that controls how Web pages actually look on screen.

Read The Lean Start-Up by Eric Reis to understand the business theory behind this approach.

Good luck, leave comments, I’ll answer them!

Vlad Gyster is co-founder and CEO of H.Engage, a technology used by companies to create engaging employee communications. He can be reached at vlad@hengage.com.