Google Screws Up Another Enterprise Charge with Outlook Sync [UPDATED]

(MoneyWatch)  Google was touting its new approach to making Google Apps work with Microsoft Oulook. But it now appears that Google Apps Sync for Microsoft Outlook may disable Outlook's the ability of Windows Desktop Search to search Outlook data. If Microsoft is being up and up about the bug report, then it's another example of how far Google has to go to turn itself into a vendor that enterprises can trust.

My colleague Michael Hickins and I have debating Google's effectiveness in going after the enterprise. He has argued that Google had just made another inroad into the data center while I said that the company badly wanted a foot in the enterprise door but that it really needed to invest in infrastructure and support to woo this market. Given this bug report, I'd go further and say that Google has just shot itself in said foot.

On one hand, yes, this is just a bug that can probably be fixed. But look at this problem in context. Google's announcement was effectively stating the following:

1. We understand that corporate end users like to use software they're familiar with because they don't want to spend the time to learn something new.
2. We know that IT departments have to keep users happy and don't necessarily have the resources to roll out new software to everyone, train them, and handle the inevitable flood of support calls.
3. We can play nice with legacy systems of all sorts and can make it possible for companies to save money while avoiding disruption of their activities.
4. By releasing this software, we're telling you that we've figured out how to solve the problem and keep everyone happy

To roll out Google Apps Sync with such a monumental error in it shows a misunderstanding of the needs of corporate customers that is profound and apparently pervasive throughout the company. Clearly no one in engineering, marketing, support (Does Google do support?), production, or management bothered to try the product past a cursory "we've got mail" stage to notice what should have been an easy find in any Q&A process. How could no one try searching for an email, at least? Wouldn't that seem to be one of those things that you couldn't do without?

Perhaps the problem is that Google revenue is so independent of what it does on the enterprise software front that it just doesn't matter. A new software package? Hey, make sure it's "cool" and call it a beta. Only, don't hold your breath while you wait for the corporate customers to line up. They're probably still trying to find a phone number to call.

[UPDATE: A Google representative emailed to note that it was Windows Search that was unable to search Outlook data, not Outlook itself. He also wrote, "We're working with Microsoft to enable search with Windows Desktop Search as well." It's a somewhat less serious issue than not letting Outlook search, but still stems from the same point. The representative also noted that Google offers "24/7 phone support for Apps," but as one BNET story comment, anonymous but self-identified as a Google Apps premier admin, noted, getting support can be more difficult than it sounds.] Image via stock.xchng user daycha, site standard license.