My big email switch: Why I picked Office 365 over Google Apps

Over the past few weeks, I've been detailing my move from an independent Exchange hosting provider to Microsoft's Office 365 service. In my first two installments, I discussed Microsoft's surprisingly exceptional technical support for Office 365 and the questions of when you get the Good Microsoft and when you get the Bad Microsoft.

But, until now, I haven't explained why I chose to migrate to Office 365 and not Google Apps. I'll tell you this: it wasn't an easy choice, and for some surprising reasons.

Some background

I've been using Exchange since 2002, when I started the OutlookPower Web site. Prior to that, we were actually using the incredibly easy-to-administer Mac-based Eudora mail server, which ran on a Mac. But when ZATZ decided to add an Outlook-centric site, I thought it would be a good idea to eat our own dogfood. To become familiar with Outlook and Exchange, we moved from Eudora to Outlook.

By the way, this wasn't the first time I did the dogfood thing with our email environment. Way back in the mid-1990s, I was the editor of the print newsletter Insider for Lotus cc:Mail, produced by the Cobb Group, an ancestor company of ZDNet sister site TechRepublic.

Way back then, since I was editing a publication about cc:Mail, I decided to use it for the company mail server. That was a wacky experience. The cc:Mail environment ran on DOS (yes, I'm not kidding), and each piece of the mail server (the database, the incoming mail exchanger, the outgoing mail exchanger) needed to run on its own physical server box. It took four or five physical machines to run this one mail server. Talk about technology in need of virtual machines, eh?

So, jump forward to 2002 when I was now runing a site about Outlook. I decided I'd use Exchange. Exchange is a lot like chess: relatively simple to learn, but takes a lifetime to master. I didn't quite realize that at the time, so I set up an Exchange server, moved us all to Outlook, and was happy ... until the day it all went to crap.

My Exchange server blew up. Literally, the drive inside the server exploded into dust (literally).

 Unfortunately, while I had lots of backups, I didn't know (or at least take seriously) the warnings about needing a second Exchange server on the network for Active Directory continuity, and when my sole Exchange server (and domain server) turned to dust, recovering it was a 13-day nightmare.

Long story long, after that, I decided I'd rather let an expert manage my Exchange server. An IT friend of mine recommended a regional hosting provider that he'd worked with for years and found reliable. They also had two additional benefits: $9.95 per month per users, and unlimited mail storage.

So I switched. Since then, I've been using this regional hosting provider for 11 years, quite happily.

Unfortunately, in the past six months or so, the company changed its business model (probably in response to Office 365), de-emphasizing Exchange and adding other hosting services.

My Exchange email flow reliability has begun to deteriorate.

Email is my income's killer app. I need to check it constantly to be responsive to projects I'm working on. Three hours of downtime is deadly. I could slip on something important or not respond to an urgent request. My hosting provider started to have mysterious outages. Then, their support site changed, and all the materials on the support site were unrelated to the sort of account I had. You get the idea.

It was time to look for another provider.

The case for Google

The case for Google was pretty simple. The two organizations I work most closely with, CBS Interactive and UC Berkeley, are both Google shops. I am in contact with my CBSi colleagues constantly — all day, every day — and I have some interaction or another with the University of California each day as well. The nonprofit I work with is also a Google grantee.

As part of my daily work, I often need to connect into CBSi or UC Berkeley files on Google Docs. I get sent links that require a Gmail account ID, and so forth. The case for Google is the theory was that if I moved fully into the Google world, then all this would become much more smooth.

It would also avoid the occasional problems of someone sending me a message directly to my never-checked Gmail account, instead of my main email account, since they'd be one and the same.

Another plus is that I rely constantly on Google Calendar. I've managed to make that application jump through some amazing hoops and have it customized in such a way that it's one of my most critical management applications. I use it not just for appointments, but for project management as well.

Google would be slightly less expensive, too. At $50/year per seat, it would cost us $100/year for my wife and me, vs. the $240/year we're spending now, or the $360/year that Office 365 would cost.

Some of that savings would be lost, because I use PowerPoint constantly for work, and I'd have to buy PowerPoint licenses no matter what. I'd probably also need Word, since I do a lot with collaborative review markup in Word. While we have a bunch of Office 2010 licenses, I'd probably need to buy at least two new Office licenses, at least sometime in the next few years.

But still, the idea of going all-Google, all-the-time was attractive.

Next, let me tell you the case for Office 365, and then I'll tell you about the big deal-breaker with Google that made the Google choice a really bad idea.

The case for Office 365

Let's start with the big one: we've been using Outlook for 11 years, we know it intimately, we're comfortable with it, it works, and all our data, rules, customizations, and more are Outlook-centric.

Some of you may not like Outlook, but I actually like using it more than Gmail. But, as a test, my wife set up a Gmail account for one of her hobbies, and used it to correspond with other hobbyist friends, and discovered that she just didn't like Gmail much, either.

So, from the personal preference point of view, Outlook still had a lead.

Then there's the whole Office thing. My wife and I each regularly use three copies of Office on the three machines each of us use (that's a total of six licenses). Although our current Office license would do for a while, I really wanted the latest PowerPoint (the merge-shapes feature was the big draw).

When you sign up for Office 365, you can get Web access to the Microsoft apps for a lower price, or five licenses per user for the real, desktop Office apps for $15/mo per user. Since this was only $5/month more than we were now paying just for email — and it also added SharePoint, Lync, and a variety of other services I'm not using now but probably will — it's actuallhy a pretty good deal.

Moving to Office 365 would be relatively straightforward since our existing Exchange environment could be migrated to the new one and all our accounts would pretty much stay the same.

Once moved to Office 365, life would remain essentially unchanged compared to the way we worked before migrating.

The cost case

There wasn't a huge cost difference. Office 365, for the plan I chose, would cost $120 more per year over what we spend now, for both of us together.

If we went to Google Apps, and then bought a home Office license, we'd save $40 a year over what we pay now. But since I use Office for business, I'd be uncomfortable with a home license to Office, so we'd wind up paying more — pretty much around the same as with the Office 365 plan.

The net-net was that the cost difference between the two plans was ultimately so negligible, it didn't factor into my decision at all.

The big factor, the really big factor, was the Google account problem. That's next...

The Google account fiasco

Explaining this is going to make my head hurt. Everything about Google accounts makes my head hurt. Let me preface this by saying I'm probably going to get some of the details wrong. Google accounts are so convoluted that the details are quite confusing.

If you're thinking about going here, you'll need to do your own research, not just rely on what I'm telling you.

Here's the key gotcha: if you move to Google Apps, you can't take your individual Google account into Apps.

Explaining this is going to make my head hurt. Everything about Google accounts makes my head hurt

That means that whatever Gmail email account you may already have, the one tied to your calendar, chat, incoming Gmail, your YouTube favorites, and on and on and on would not be tied to whatever account you get for Google Apps.

It's possible to do some finagling.

For example, you could share your existing Google calendar with your new account and give it read/write access. You could set up a forwarding filter from the old Gmail account to the new one. You could grant access to your Adwords and Adsense settings to the new account.

But other things aren't so straightforward. Have a ton of contacts in Google Chat? You'd have to go and re-invite each one to your new account. You couldn't use your existing Gmail account name, so if you happen to like your existing Gmail account name or if it's something people are long familiar with, say goodbye.

And if your existing Google account is a member of a Google Group or has sharing privileges on Google Docs documents, all of those would have to be changed to your new Google account. Add to that phone numbers attached to Google Voice, and you have a real mess on your hands.

Yes, sure, you could still use your old account, but if that's the case, and you're trying to go for an integrated, holistic whole, having to constantly switch between a new Google Apps account and a legacy individual Google account shoots the desire for a well-oiled, cohesive messaging infrastructure right out of the water.

Throughout the whole Google Apps environment, there are little gotchas about how you transition your account, and what you can and can't do when moving to an Apps account from an individual account.

Personally, I think this is ridiculous.

Most people will likely have started with individual Google accounts and gotten to like Google services, and then decide they want to move to Apps. To force people to either lose all that infrastructure, or have to do a whole pile of hoop-jumping to make it work seems wildly counter-productive.

How I made my choice

In my case, I realized it would be far simpler to move my Outlook from one Exchange hosting provider to another.

If I instead moved to Google Apps, all my long-standing Google Chat connections would have to be re-invited. I have a ton of these and I didn't relish having to explain this whole process in gory detail to the half of them that would demand some sort of backstory explanation. All of the projects and groups I'm involved in with for work would have to be changed, which would mean I'd have to assign twenty or more administrivia to-do items to some already extremely busy people.

Plus, there was the chance everything could go wrong. I had a situation a few years ago where I had a Google account, gave it a backup email address, and it decided to make some severe changes to the original Google account because it already had the backup email account listed with some other service. That situation was never fixed, because the Googlers I eventually managed to talk to said there was nothing that could be done. It was just what happened.

Add to that the fact that neither my wife and I particularly like using the Gmail interface (and given I spend so much time in my mail environment, that's important), and that there was really no cost advantage when factoring my specific need to purchase Microsoft's Office anyway, and the decision was becoming clear.

What really clinched the deal for Microsoft and against Google was the homework problem. I didn't want to have to be a squeaky wheel to my busy CBS Interactive and UC Berkeley colleagues. I didn't want to make them all change my chat names, change my account access to all our shared documents, and make them re-invite me to all the groups I rely on to do my daily work.

The bizarre moral of this story is I would actually have less service interruption and more service continuity for my existing mission-critical Google services if I switched to Microsoft Office 365 than if I switched to Google Apps.

And that's why I switched to Office 365. So far, two weeks in, it's all running quite smoothly, both my Google accounts and my email on Office 365.

I have one more story coming in this series: how I moved a half million email messages between services. That's coming next week.