Google Apps product manager Shan Sinha was once director of strategy for Microsoft SharePoint, Redmond's longstanding effort to facilitate business collaboration over the net.

Sinha left Microsoft in the fall of 2007 to create DocVerse, a service that bypassed SharePoint, plugging Microsoft Office clients into Google Apps. Sharepoint, he says, just wasn't working.

"Lots of people seemed to be adopting SharePoint, but few were really using it," he tells The Register. "SharePoint was one of Microsoft's fastest growing businesses ... but as it turns out, end users found it too complicated. It was too limited in how you could actually share documents and files."

Less than three years later, Google acquired DocVerse, and in February, the service was relaunched as Google Cloud Connect, with Sinha assuming control of all Google Apps "messaging" services. This included Gmail, Google Calendar, and Google Contacts, as well as the email security, encryption, and archiving tools that came with the company's acquisition of Postini.

Sinha's story is a convenient metaphor for Google's enterprise business as a whole. Google isn't just taking on Microsoft. It is turning Microsoft's aging Office business against itself.

In addition to plugging Microsoft Office into Google Apps via Cloud Connect, Google has turned Gmail into a Microsoft Exchange backup service. Google is now offering a plug-in that transforms Outlook into a Gmail client. And now, as Microsoft prepares to launch its latest online business-productivity service – Office 365 – Mountain View has called on Sinha to tell the world why the new Redmond suite pales in comparison to Google Apps.

On Monday – a day before Microsoft's Office 365 release party in New York – Mountain View unloaded a blog post from Sinha entitled "365 reasons to consider Google Apps".

The post includes only four reasons, but you get the message. It is the same message that Google was intent on delivering when The Register was summoned to the company's San Francisco outpost last week for a sit-down with Sinha. Clearly, the meeting was meant to answer Redmond's big launch.

Shan Singa

"Google is a company that's not falling victim to baggage from before, compromising products out in the market. They have the privilege of completely rethinking the way things should work," Sinha told us.

"[Office 365] still seems like a repackaging of a lot of things that Microsoft already has – which is the sort of thing Microsoft has done for its entire history. Yeah, you're still using Exchange in the cloud, but you're still using Outlook on the desktop. For collaboration, it's still SharePoint, this very clunky thing."

Office 365 is a subscription service offering hosted versions of Microsoft Exchange, SharePoint, and Lync, the Redmond platform that combines IM, VoIP, and video conferencing.

The service also includes access to Microsoft's Office Web Apps – versions of Microsoft desktop clients that can be used from a browser – but these offer a rather limited set of tools. Office 365 is primarily meant for use with Microsoft's desktop Office suite. Some Office 365 plans actually include subscriptions to a version of desktop Office.

Preemptive strike

In other markets, Google rarely goes out of its way to attack the legitimacy of the competition. It typically leaves such heavy-handed tactics to the Microsofts of the world. But in recent months, Google appears to have taken a very different approach with its enterprise operation.

Last November, Google actually sued the US Department of the Interior, claiming the federal agency didn't give Google a fair shot at winning the $49.3m contract it awarded to Microsoft. And Google's preemptive attack on Microsoft Office 365 is lifted straight from the Microsoft PR playbook.

"Technology inevitably gets more complicated as it gets older," Sinha's blog post reads. "Upgrading platforms and adding features results in systems that are increasingly difficult to manage and complex to use. At times like these, it's worth considering a clean slate: an approach based on entirely modern technologies, designed for today’s world."

The old technology would be Microsoft's. The "clean slate" would be Google Apps.

In some cases, Sinha's argument is mere posturing. "Office 365 is for individuals. Apps is for teams," he says at one point, without actually comparing Apps' collaboration tools with those of Microsoft. And he sidesteps any mention of the inherent limitations of Google Apps.

He doesn't say that Google's web-based applications can't quite match the tools offered by their counterparts on the desktop. And although he points out that Google Apps is "designed to work well on any device, on any operating system," his post doesn't acknowledge that Apps cannot be used when you're offline. Speaking with The Register, Sinha said that offline Google Apps is still scheduled to arrive sometime this summer.

But there's one area where it is hard to argue with the man. In January, Mountain View updated its Google Apps contracts so that they no longer make allowances for scheduled maintenance. The contracts guarantee 99.9 per cent uptime, and any downtime – no matter how small – is counted and applied to the customer's agreement.

Previously, Google's service level agreements (SLAs) made allowances for scheduled downtime, and they never counted downtime of less than 10 minutes towards the customer's contract. When the new agreements rolled out in January, Google called them an "industry first", and Sinha told us last week that he's still unaware of any competitor offering a similar guarantee.

In 2010, Google says, its services were up 99.984 per cent of the time. And through first several months of 2011, they're at 99.9949 per cent. That translates to about five minutes of downtime per month.

Google Apps runs across a highly distributed back-end infrastructure, so the company can take down servers in one data center for maintenance while servers in another data center – or another part of that same data center – handle the load.

"One of the biggest differences between Google and Microsoft from a hosted standpoint has really been the reliability of the suite," says Michael Cohn, founder and chief marketing officer of Cloud Sherpas, a company dedicated to facilitating the use of Google Apps and which has weaned myriad businesses off Microsoft tools.

"Outages that Microsoft BPOS [the precursor to 365] has been incurring – both scheduled and unscheduled – have shown that whereas Microsoft has proven it can build enterprise software, it's not necessarily as good as even some of their partners in hosting software."

Cohn has vested interest in the success of Google Apps. And he acknowledges that Microsoft's ways could change Office 365. But Google's SLA backs him up. And Redmond's case wasn't helped by the outage that hit Microsoft BPOS just last week.

'Traditional Microsoft'

Sinha also argues for the simplicity of Mountain View's pricing structure. Google Apps sells for $5 per user per month – or $50 per user per year – whereas Microsoft offers three separate "editions" of Office 365 and 11 different pricing plans.

Some include desktop software, others don't. "The Office 365 licensing schemas are traditional Microsoft. It's very difficult to understand," says Michael Cohn. "Once you start comparing apples to apples, I don't think the cost of Microsoft's suite is all that attractive."

Yes, there are add-ons for Google Apps that cost extra, and you could always debate whether Google's setup is actually more cost effective than Office 365, a service that hasn't even launched yet. But the point here is that Microsoft is straddling the old world and the new. The plans are quite difficult to grasp. And whether purposely or not, Microsoft's literature blurs the importance of desktop Office to the service.

Office 365 continues Microsoft's move onto the web, but this move is only partial. Microsoft is shifting to a direct model, but it is still hoping to keep its existing resellers happy.

As Sinha admits, Microsoft has "inertia" on its side – so many businesses will use Microsoft only because they've used it in the past – but Redmond is also burdened by the old client-server model that was sold through the channel. However you slice it, this comes with added costs – and added hassles.

You can criticize Google's UI. You may balk at putting your data on Google's servers. But delivering all software across the web, through a browser, is at least a triumph of simplicity. You need never to update a client.

And all server-side updates happen automatically, from inside Google's data centers. According to Google, its customers received more than 125 new tools over the past year. If you can get by without all those extra tools you get with a desktop client, that $50-a-year price tag is quite a bargain.

The other point here is that Google is determined to beat Microsoft at its own game. Google is primarily an online advertising company. But it very much wants to be something else. If nothing else, that's the message delivered by Shan Sinha. ®