Back when every single desktop needed a copy of Office (or at least when the powers-that-be assumed every desktop should be Office-equipped), forgoing Office apps on most PCs was unthinkable. That's changing. Now, it would be worthwhile to take a hard look at how badly your organization needs a chicken in every pot.
Office 365 vs. Google Apps: Ease-of-useOnce again we're back to Queen Elizabeth 2 vs. the Sloop Google. It all depends on what you want to do.
If you're accustomed to using Outlook on the desktop, the Outlook Web App will look more or less familiar, whereas Gmail may turn your world inside out.
If your users are accustomed to Word, Excel, and PowerPoint, the Office 365 choices don't change a thing — quite literally a zero learning curve. On the other hand, if your people are using Google Docs at home already or if they've come to loathe Office's more frustrating aspects, perhaps the much simpler Google Docs approach will fit the bill.
Over time, Gmail and Outlook.com have come to look and act much alike. Although there are purists who would argue the supremacy of one over the other, on balance, I find it just as easy (or as hard!) to wean people from desktop Outlook and onto either online service. If your transition to Office 365 includes moving to Outlook.com, you're in for some user pushback. On the other hand, if most of your users already have online email accounts, going to either Outlook.com or Gmail should be a relative piece of cake.
Assuming you come from an Outlook shop, and you're going to continue using Outlook on the desktop, Office 365 will fit like an old glove. Since many (if not most) office workers these days are familiar with online email systems, the learning curve for Gmail shouldn't be daunting. Getting used to Google Apps might present a few challenges, but most will find it quite straightforward, particularly if they're inured to the complexity of Office.
Office 365 vs. Google Apps: AdministrationAdministering an Office 365 installation can be demanding, precisely because Office 365 offers a wide array of options. Many admins who aren't used to handling Exchange, Lync, or SharePoint will need experienced help to get the beast up and running. Administering Google Apps for Business is comparatively easy because the choices are straightforward and well laid out.
Office 365 has so many nooks and crannies, as well as so many tools at hand, that someone new to the product would be well advised to look into everything on offer — that means training, lots of time with Google (er, Bing), participation in one or more of the online fora, and likely consultation with other folks who have been around the block a few times.
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