Shifting from Outlook to Google Mail (et al.)

As noted before, I signed up for a pilot in my company, evaluating GMail, Google Calendar, and Google Apps as potential replacements for Outlook and Office.

After much behind-the-scenes maneuvering about, the project team kicked off the pilot today with an hour-long presentation by Google.

Well, that was something of a waste, as I am already well-familiar with GMail and Google Calendar, and passingly familiar with Google Apps (though new to Google Sites). But the fact is, nobody (including Google) really thinks we’re going to give up Office for Google Apps (except for some extreme field setups, but that’s it). GMail and GCal, though — those remain possibilities.

So for me, I just wanted someone to walk me through (or point me at) the data conversion. Listening to the Google folks explain GMail worse than I could was just painful. Plus, unlike most software evaluations where we’re usually struggling with the vendor to give us more features than what they have, with Google we’re (officially) pushing back a bit to restrict this, that, and the other thing, based on Official Company Policy and Security Stuff and IT Dictates and the like.

*sigh*

After the presentation this morning, we were told we’d be sent something telling us about how to do the conversion. In the meantime, I verified that I could access my company GMail account. In order to keep it from interfering with my normal GMail login, I actually downloaded Chrome and am running the office stuff there, my home stuff in Firefox. And, as long as I can avoid it, nothing in IE.

Also while waiting, I started playing with GCal to be able to see my home calendars (mine, Margie’s, Katherine’s, and the Consortium). Now that’s integration, baby.

Finally got the documentation shortly before leaving the office. And I noticed that they had started mail forwarding from Exchange to my GMail account already. Woot!

The conversion doc basically pointed at two tools. The first is the Google Email Uploader. Woot! Where have you been all my live, baby? This is the tool I needed when I moved to GMail in the first place, as it can migrate stuff from Outlook, Outlook Express, or Thunderbird. In fact, using it, I plan to both migrate my old-old-old Thunderbird mail (thus letting me clean that off my hard drive) and (now that I am gradually getting Margie onto GMail) Margie’s mail, too.

Well, maybe. See, I had spent several hours yesterday and into last night cleaning my Outlook account to have just a few weeks of mail in it. That left me with a mere 2,000 messages or so to migrate. The uploader worked fine with an offline Outlook setup, by the way.

Still, with 2,000 messages, it took about three hours to migrate. I note that the Uploader told me I had about 60K messages in Thunderbird. Yikes. That’s a lot of uploading.

Nevertheless, the upload was successful and relatively painless. The Uploader optionally creates labels (tags) based on the folder in Outlook the message came from, which is handy as a foundation. I still had to create filters for each of the labels. That took quite a bit of time (as I have lots of folders / labels), and I’m sure it will be an ongoing process.

Contacts were brought over cleanly, too. Does make me wonder, though, about doing Christmas Card labels come December … 

The calendar conversion is separate from mail, and depends on my old bete noir, the Google Calendar Sync tool. It’s a bit better than the last time I struggled with it, though still a bit flaky for some private and repeating appointments.

One area of concern I had (and still have, some), is that my account in Google Apps is dave.hill@mycompany.com. But I’d already created, at one point, a calendar, etc., using that login name (and, in fact, it’s still out there). Fortunately, Google seems to be smart enough to distinguish between a private account by that name and a corporate / Google Apps account. In one case it’s warned me of the duplication, but let me proceed with the correct one. In other cases, it’s done just fine based on the password I’ve given it. In still others, it simply hasn’t made a difference.

The one case where it did was that I ran through a calendar sync … to the wrong dave.hill calendar. So I had to rerun that to the correct (corporate) one. And, as in previous iterations, it somehow doesn’t pick up a bunch of recurring meetings I’ve been invited to. Takes a comparison between the two systems to spot the deltas, to be followed by several emails to folks asking them to resend invites to stuff.

Meanwhile, the other twist in all of this is my Blackberry. I’ve had GMail on there previously … but how will the new arrangement work, esp. since I’ll be turning off BES pushing of Exchange stuff to the Blackberry mail and calendar?

Well, so far, so good. GMail on the BB has a pretty easy toggle between accounts, so I can shift between office and home email with just a few menu clicks. 

The calendar stuff is a bit more problematic — the out-of-the-box for GCal is a web setup that provides minimal functionality — a list of calendar entries for the next few days, plus a box to create a quickie new appointment. Pretty crude.

But there’s a recommended Google Sync for Mobile that will sync up my Google Calendar and Contacts to the actual Blackberry calendar and contacts info. Sweet, if it works properly. There is, supposedly, something similar (in beta) to sync between GMail and the BB’s mail app — but then you lose a lot of the keen GMail goodness (e.g., search), so no thanks.

There are things I already miss about Outlook. Among them:

• Google is barely, barely getting into the Task list business. I will miss the Outlook task / to-do list functionality (though its translation onto the Blackberry sucketh mightily, making it less useful than it might have been) (though Google doesn’t even support any sort of task stuff on the BB).
• GMail’s ability to provide customized (standard) formatting, vs. Outlook (both custom font setpus for messages as well as for the sig line) is pretty limited. So far as I can tell, you can have a standard sig line in any color you want as long as it’s black and Arial. Harrumph.
• Our company’s 90-day email retention policy creates problems. In Outlook/Exchange I had a monthly ritual using MessageExport to pull email/attachments out that I wanted to save. I have a reputation for being the go-to guy for mail archives. Getting mail exported out of GMail, though, is a lot more problematic. I must ponder this.
• I liked being able to color-code groups of calendar appointments (phonecons vs meetings, personal items, must-do items). GCal uses a single color (saving color differentials for other calendars you can view in parallel).

On the other hand, I’m finding the inclusion of GCal info on my GMail window and in invitations that I receive to be delightfully functional.

Overall, pretty darned happy about this, and looking forward to using it. My biggest concern at this point is that we’ll have to roll back to Outlook eventually …