The era of cloud-based collaboration technology is here. Forrester's last survey of collaboration software decision makers showed that 67% are planning to or already deploy collaboration software-as-a-service (SaaS). Buttressing this stat is the incredibly high volume of inquiries I've received over the past two quarters from business and IT leaders trying to decide between Microsoft technology and the Google portfolio. The questions were so numerous that we published a report to answer our clients' basic queries. The increased activity, however, obscures the fact that we're still in the early days. As our report shows, IT leaders are still trying to get acquainted with cloud technologies: What features are in the suite? Is it secure? Are businesses like mine using it? These are essential things to know, yes. But they don't fully tell the story of how a company can get the most out of a cloud collaboration and productivity suite implementation. So, as you examine Microsoft Office 365 and Google Apps for Business, here are five more questions you need to address at the outset:

  1. What do these tools actually enable our workforce to do? Many IT leaders approach the choice between Microsoft's and Google's respective offerings as a simple price and features trade-off. This simply is not so. These two vendors have fundamentally different philosophies on how collaboration technology is developed, deployed, and consumed. So, as a business considers these offerings, executives should have a vision for what they want employees to be able to do in the next five to ten years and select the solution that is aligned with that vision. For example, many Google clients we speak with note that they chose the Apps portfolio because Drive allowed for collaborative, real-time document creation.
  2. How can we make this solution secure? This conversation can often be a show-stopper: This tool doesn't support this security protocol out of the box? We can't use it! What that thinking overlooks is an ever expanding ecosystem of third-party cloud vendors well positioned to provide additional layers of security to a cloud collaboration implementation. For example, Vaultive provides email encryption services for Microsoft Office 365 and CloudLock has a data loss prevention (DLP) solution for Google Drive and Google Sites. This sets up a situation not all that dissimilar to what IT leaders encountered on premises: A network of partners that fill gaps the vendor has in their base offering. And those in the IT and security groups must be willing to look at these types of solutions in conjunction with the cloud collaboration portfolio.
  3. What are the unexpected costs? Our data indicates that reducing cost is rapidly falling as a reason to move to cloud (dropping from 71% in 2009 to 56% in 2012), but the low cost of Google Apps and Office 365 is still seductive. However, as the preceding point shows, that base price for a seat can be misleading. Additional security, disaster recovery, storage, support, and other ancillary services can quickly raise the per user price. For example, adding eDiscovery and data retention features to a Google Apps account changes the package pricing from $50 per user per year to roughly $100 per user per year. Adding a DLP solution like CloudLock will add another $15 per user per year. So, IT leaders building business cases on costs must have a real grasp on the all-in costs of their current implementation and working knowledge of the fully-loaded costs of moving into the cloud.
  4. Are these the only two options for the cloud? The conversation about the cloud is currently dominated by Google Apps and Office 365. But these aren't the only options for enterprises looking to move their email into hosted environments. IBM is still very much invested in the collaboration software business and has an offering — SmartCloud for Social Business — that has gained traction with mid-market firms and enterprises like Newly Weds Food. Also still in the game are the hosted collaboration services providers like SilverSky (formerly and Avanade that came of age before the launch 2007 launch of Google Apps Premier Edition. These hosters are carving out a space for themselves handling the deployment complexity that aren't always addressed in multi-tenant collaboration offerings. IT leaders must account for the entire cloud collaboration and productivity landscape as they evaluate the cloud. This will prevent any hasty conclusions (re: "We can't move into the cloud because no vendor meets our needs.").       
  5. What should we look for in an implementation partner? Most of the businesses that have moved into either Google Apps or Office 365 that we've talked to required assistance from consultants on the implementation. However, these emerging online collaboration portfolios have also opened the door for new implementation services providers, such as Appirio and Cloud Sherpas, which are bringing additional capabilities to the table, like mobile application development and cloud management services. As IT leaders look at the transition they are making to the cloud, they should also consider what the workforce will need to make the transition work: Integrations with other cloud services? Custom mobile apps that use a cloud service as a backend repository? Centralized management of multiple cloud services? Change management guidance? This needs evaluation should guide how you look at both established systems integrators spinning up cloud practices, like Capgemini, and the upstarts that came of age with cloud services.


Update: In the original version of this post, we incorrectly described the change in pricing for Google App when including Google Vault as adding $10 per user per year to a Google Apps seat. The text has been revised to reflect the price difference between Google Apps with and without Google Vault.