Last week we heard Larry Dignan posit that perhaps Google's best chances to penetrate the much sought-after enterprise applications market would be by using some variant on their existing search appliance which would have their full Apps suite but allow skittish enterprise CIOs to host on-site.

Now, Robert Scoble suggests that data synchronization services such as Cemaphore (which allows synch between Gmail and Outlook via Exchange data-mapping to the Google system) might be the better plan.

I have to side with Scoble on this one. There are certainly some CIOs who love appliances (heck, I love appliances!) but historically, the way to break into the enterprise has involved being more flexible than the existing market-leaders. Microsoft made headway against Novell because they made it easy to migrate from Novell. As Scoble points out, no one likes volte-faced changes in huge and complicated systems. It's messy and inefficient. But if you can introduce something which will work seamlessly within the system even as it allows you to transition away from it, that's an easy sell.

Whether this is initiated by CIOs or the users (Scoble, for some reason, thinks that CTOs are eager to let their users use whatever they want to get work done... not in my world!) hardly matters. Once the technology is in broad use, and is effective, it is fait accompli. To the extent that Google or third parties can provide seamless integration technologies for Apps, they will certainly improve their ability to penetrate the enterprise market. I would argue that these tools are really aimed more at users, however; CIOs and CTOs want to see other things from Google before they start putting an official stamp of approval on Apps, like significant real-time support and heavy duty SLAs. It's nice for CIOs to have access to tools such as Cemaphore and no doubt that will encourage some to move; but their view is very different from that in the trenches (for good or ill). CIOs make enormous, disruptive changes all the time, often for good reasons, but the point is that it's not simply a lack of integration tools that is preventing the leap to Google right now. There are more pressing concerns that will have to be addressed before most CIOs will consider committing their company to the cloud.