Why We Don't Support Desktop Mail Clients (like Outlook) with Gmail

My original hope was that "switching to Gmail," for the majority of users, would consist simply of changing a few settings in the mail client. After all, we're trying to make this transition as smooth as possible, and we can effectively guarantee a successful transition if the only thing that changes for the user is the mailbox size. All of the other things (like Google Docs and new calendar features) are still available for the users who want them.

It didn't end up working that way, though. We certainly think it's for the best in the long run, but it's been making employees a little more hesitant to make the switch.

So why not?

Keep in mind that as a campus, we've made a significant shift toward using Apple machines. Most of our students and employees are using Mac OS X.

Outlook 2011 (Mac) ONLY supports calendar and contacts through Exchange.

That's right. On the latest version of Outlook for the Mac, you can get your mail through IMAP, but for anything else, you'll need an Exchange account. Google provides a special utility that supposedly makes Outlook fully-integrated on Windows, but no such utility exists for the Mac. After further research, I can confirm that this is not due to a lack of interest from Google. Outlook 2011 provides some abilities to developers for interacting with it, but nothing that would overcome this obvious problem.

Outlook for Mac 2011: The straw that broke the camel's back?

This puts our IT Department in a tough position. On the one hand, we've been really pushing for the use of Macs over Windows machines based on the position that software incompatibility issues are, for the most part, overstated. On the other hand, though, we have a clear-cut example of Windows software that works just fine... and its Mac counterpart is inadequate. Imagine how we'll look when we have to tell users,

"You can keep using Outlook if you're using Windows, but if you're on a Mac, you can't."

The more we thought about it, though, the more we realized that this isn't a problem with the Mac. Getting your Gmail working with a Mac is quite easy, and it became even easier with Lion. This is just another issue of Microsoft's own software not working as it should. We were similarly frustrated when changes with Exchange Server 2010 led to us having to pester users to upgrade Entourage (the precursor to Outlook on the Mac) because the new Exchange no longer supported WebDAV. That is: key features of Entourage would simply stop working after Exchange is upgraded. How is that, in any way, acceptable?

One of the reasons we're moving to Google Apps is to rid ourselves of dealing with Microsoft's annoyances, and even as we're doing it, Outlook 2011 manages to reinforce that decision.

Mail and calendar clients change often

Even if we were a completely Windows campus, though, what guarantee do we have that the next version of Outlook will integrate with Google Apps? Perhaps more relevantly, what possible excuse would we have if it doesn't? The snake has already bitten us time and time again. If our Mac users are already learning the new interface, why prolong supporting something we don't even know will work next year?

Just working, though, is only part of the issue. If there's anything I've learned through this process, it's that people like things to look exactly as they have, and any change (regardless of how small) will be met with resistance. We all remember the user interface overhaul of Microsoft Office in 2008. Whether the UI was better or not, it was very different, which was very negatively perceived. Of the few employees still using Windows prominently (through virtualization or otherwise), it's not surprising to see many of them still using Office 2007. People don't like change.

Microsoft isn't the only company to change a user interface, though. Apple Mail has been revamped for OS X Lion, and while it won't be an issue (since most employees are using Outlook or Entourage), I feel quite confident that it would be if we configured it commonly. We can't expect user interfaces to stay the same, though, right? So how does Gmail relate to this?

Since you're loading the latest version of Gmail each and every time you open your Gmail, that alleviates a lot of these issues. Likewise, Google tends to keep Gmail interface changes fairly minimal, so users will be using the latest interface... only without the shock of a completely new interface. Users don't have to get re-accustomed to how to manage their e-mail every time their machine is upgraded or a new version of Office is released. Even after a Windows <-> Mac transition, users will be already familiar with their mail.

Some Gmail concepts don't translate well to IMAP

This is a much more minor issue, but some of the concepts don't necessarily act intuitively in IMAP clients. If someone doesn't understand archiving vs. deleting, s/he might not understand why deleting an item from the Inbox doesn't put it in the Trash. If someone doesn't understand the concept of labels vs. folders, s/he might not understand why the same message is "copied" in multiple places in their mailbox. And what's to stop someone from dragging a message from the Inbox (or a folder) into All Mail (where it already exists)? In a normal folder-based structure, that'd be no problem at all.

We ended up deciding it's worth dealing with on mobile mail clients, but would, even in an ideal configuration, cause confusion for desktop users.

To be clear...

We haven't disabled the configuration of desktop mail clients (although we could). In fact, I've gone out of my way to ensure that these things will work properly. When users ask, I'll even tell them the settings necessary to configure desktop mail clients. However, this is only done with the understanding that any issues encountered are yours to troubleshoot. The web interface will always work, and works for all available features. Not only that, but it's the one we prefer personally.

It's a bit painful for switching users to learn the new interface, but it's no worse than what the next version of Outlook could be, and it holds the promise of being the last time a new interface must be learned. From here on out, it's just whatever granular changes Google implements. Just imagine how many fewer headaches all of us (users and support) will have! E-mail and calendaring will finally be the "always just works" "take-it-for-granted" tools they always should have been. I, for one, am certainly looking forward to it.

Have any thoughts? Feel free to leave them in the comments.