Evan Schuman's StorefrontBacktalk

When Target’s development team launched the new Target.com on Tuesday (Aug. 23) after two years of development, it must have felt like a dream come true. But it wasn’t—at least not for customers, who discovered that big chunks of the new site didn’t work at all, and almost nothing worked as well as the site they’d seen a day or two before. A very dangerous telltale sign: One of the most common hashtags on Twitter posts about the new E-Commerce site was #FAIL.

Why? What went wrong? Actually, not much, from the point of view of experienced developers. Naturally the site had glitches—that’s to be expected. And Target’s plan of starting with a new site that had the same basic functionality as the old site, and only later rolling out exciting new features supported by what’s baked into the new architecture, was a solid development approach. Unfortunately, although that plan worked very well for developers, it made no sense at all to customers—the people any E-Commerce site is supposed to be all about.

Target forgot the first rule of customer-facing development in retail IT: Customers expect a new E-Commerce site (or kiosk or POS system or loyalty program) to work better than the old one did. If the old one worked fine, and the new one doesn’t work as well, what’s the point?

Of course, in Target’s case, the point was regaining control of its E-Commerce destiny. From 2001 until this month, Target.com was run by Amazon. Target decided to end that arrangement two years ago—and that meant it had a completely blank slate to start from in creating a new site.

Most E-Commerce execs would love that opportunity to shed all the legacy code, the decade or so of kludges, workarounds and hacks that make it so difficult to do anything really innovative. All that old junk makes new approaches next to impossible.

But cost-justifying greenfield development when a retailer has already paid for an E-Commerce site that works? Not in the cards. That’s why most “new” E-Commerce sites are really just a new coat of paint—underneath is the same crusty old infrastructure.

Then again, that crusty old code does work. So when a retailer rolls out a refreshed site, customers see a few new features on top of the same old stuff. And the same-old, same-old still works fine.

That dream of a from-scratch new Web site will always be a daydream for most E-Commerce execs. And Target’s experience demonstrates why that’s a good thing.

No question, Target got the chance to do it right, from the ground up. But there’s a downside.