As cloud computing gains adepts in enterprises, leading to adoption of hosted suites like Google Apps, more and more CIOs are rethinking having "fat client" applications like Outlook on PCs, Pray said. "As an enterprise, I wouldn't strategically bet on the sync tool and Outlook as a client with the Gmail back end because you introduce a lot of challenges in your environment. It's better to go with the Gmail Webmail client," he said.
While that's the ideal scenario, end-users in enterprises remain very emotionally attached to Outlook. In a study published in December, Osterman Research found that only 16 percent of midsize and large organizations would probably or definitely consider switching to a new messaging back end if they had to switch desktop client software. However, 52 percent would probably or definitely consider switching if they could keep the existing desktop client, in most cases Outlook, Osterman Research found.
"I believe that Google is smart to focus on letting users keep Outlook as their front end for Google Apps. This minimizes training costs, end-user disruptions and the like, since users tend to be sensitive to changes in their email experience," Michael Osterman, Osterman Research's president, said via e-mail.
Burton's Pray has seen Outlook sync tools come and go over the years from a variety of vendors, usually with less than stellar results, so enterprises need to adjust their expectations. "I have yet to see an Outlook connector that works well and is successful," he said. "The main reason is that you can never truly put in the time and effort to build the connector to be robust enough to support the exact user experience you get with Outlook and Exchange."
"You should pilot this in your organization with your users, especially power users, to get a feel for how well it's going to work, and understand there will be gaps in functionality," Pray added.
Indeed, while Google argues that its tool replicates most of the Outlook-Exchange functionality end users need, like basic e-mail, calendar and contacts, there are many features and capabilities that it doesn't, including synchronizing tasks. Google offers a nifty chart outlining what its sync tool does and doesn't replicate in this page.
"It supports a very small subset of what Outlook can do," said Tom Rizzo, a senior director in the Microsoft Online Services team. In particular, the Google tool doesn't scratch the surface of most new features in Outlook 2010, which like the other components of Office 2010 are much more "socially aware," thanks to elements like the new Outlook Social Connector, and let users collaborate in cloud computing environments, according to Rizzo.
The tool has also been affected by several pesky bugs, including a recent one that prevented it from downloading some email messages from Gmail to Outlook, forcing affected users to regularly check their Gmail inbox.
Overall, Benjamin Congdon, a Google Apps systems architect and consultant in Ontario, likes the Outlook sync tool but suggests Google stamp out the bugs faster. "If they can keep up with the 'known issues' as quickly as they become known, that will greatly assist in building a better relationship with the Apps admins out there," he said.