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

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

Summary: The bizarre moral of my migration story: I would actually face fewer service interruptions and more service continuity for my existing mission-critical Google services if I switched to Microsoft Office.


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).

shattered drive 3-1
(Image: David Gewirtz/ZDNet)

 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...

Topics: Microsoft, Google, Google Apps


David Gewirtz, Distinguished Lecturer at CBS Interactive, is an author, U.S. policy advisor, and computer scientist. He is featured in the History Channel special The President's Book of Secrets and is a member of the National Press Club.

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  • Gmail is a consumer product, not a prof. mail account !!!

    Quite funny that the editor of a tech magazine doesn't get that tiny but important detail. Gmail is made for the hundreds of millions users worldwide who are fine with one gmail account and what it does for them. Hardly anyone of them is trying to pull such a stunt. Why would they ?
    Googles World is based on simple apps for simple tasks.
    • Sadly, Google convinced some companies/gov agencies

      So now I have 3 Google accounts. My personal one, one for the state of Wyoming, and one for my company I work for. The account mess talked about in this article is a serious one. I cannot change my name to include something to note the different account. So it is difficult to know which account I am in. You can login to more than one account and switch between them, but once it decides you need to login again, it will force you into one account, rather than let you login to the account you selected.
      I have three browsers installed so I can avoid the account switching problems. I use IM + so I can be active in all three for chat in one interface. And we still need Office, so it isn't like we've saved money using this setup.
      • Eat more cookies

        Open Firefox, get CookieSwap.
      • You "rape" gmail (sorry for the strong wording)

        What you do, Gmail was never intended to be used that way. You definitely need a professional email solution !!!
        I use Mozilla Thunderbird with 3 email accounts and it works flawless. Admittedly I don't do any fancy stuff.
        • No, it's those companies that need a professional solution!

          And Google's moving away from desktop clients, so you have to use the browser, even if it means running three of them.

          And no, I won't irrevocably merge my personal account with business activities.
      • Use the CNAME records

        You don't need 3 browsers.

        open a tab > login to your personal account

        open another tab > use the Wyoming specific url to login to that account or whatever it is

        open a 3rd tab > use the company url to login to that account

        Change your name? Doesn't each account have different branding, not to mention everything after the @ is different?
    • except

      that Google Apps is for professionals. so they should have professional support for email accounts and linking things together.
      • What about Live and 365 integration

        So can I then expect MS to provide the same linkages to Live & 365?
        Bradford Wright
  • Other reasons

    It's difficult for me to take any organization seriously when they are exclusively using GMail accounts. It's like handing people a business card printed on a dot matrix printer. The image you convey is that you're too cheap or poor to have your own domain-based server. Either way, it's not a good image to convey for a business trying to get people to purchase products or services. It would be far better for those companies to purchase a domain and hosting from an outfit like 1and1 and just run all of their email accounts on the host servers. You get a far more professional and recognizable email address for less money. Nobody wants to do business with a "dodgerfan15385 at gmail dot com," when they could be doing business with a "robertsmith at corporatename dot com."
    • Google Apps for Business


      We use Google Apps for business with our own domain name. It's a lot simpler and we can log in from anywhere and check mail, access google drive, etc. Our Apps for business account is based on our domain. No hassles with Exchange server, etc.
      • Live Domains.

        The product everyone seems to forget here is Microsoft Live Domains, which is what I consider to be their actual competitor to Google Apps. Office 365 is on a whole different level.

        With Live domains you can you your own domain with, which gives you access to all of Microsofts goodies like Skydrive and Office Web Apps.

        The crazy part? 500 accounts for free. Add that to the fact that you escape the formatting hell of Google docs and it should be a no brainer.
        • Great example

          I use Windows Live Domains since several years ago, I even customised it with my website's logo on the inboxes. I manage FIVE DOMAINS with one account and it works great.

          Being a heavy Apple user, both OS X and iOS, I love that Live Domains syncs Mail, Contacts, Calendars and Reminders--even more stuff than Google which no longer offer Push email--and being only second to Yahoo! that also syncs Notes. Yahoo! service is always reconnecting though.

          I have always hated relying on a web browser to do any kind of work so an email client is my preferred method of working with email and now that Microsoft supports IMAP and iWork is free on new iOS devices, I don't see why the need for Office 365 or Google—that I really hate. I hate the Google basic squared, unattractive-looking, plain, basic and assistance-less experience that is Google. Add to that the constant milling of any information that passes through their servers to serve you ads and the incredibly complicated help they "offer;" you have to look through pages and pages of unstructured information and FORUMS in order to find the help your looking for.

          "Community-based" and "open-source" to me are synonyms of cheap/unmanaged when it comes to Google.

          If I were force to upgrade from Windows Live Domains I'd choose Office 365 without thinking it, as it also offer web hosting, more SkyDrive storage and the Office Suite. Recently I was comparing cloud storage solutions and found out the SkyDrive is actually cheaper than Google Drive and Dropbox; I don't know why people go crazy over Google Drive when it forces you to download Chrome let you save offline documents, hence serving you more ads.

          You should see the sheer quantity of processes in Activity Monitor/Windows Task Manager Google creates whenever you install or run their apps. I just don't trust Google.
    • apps

      Google apps supports your own domain name.
      • It's true.

        The college I attend uses a custom GMail account that ends in .edu instead of
        Richard Estes
        • "The college I attend uses a custom GMail account that ends in .edu..."

          Same here.

          My university is switching from Lotus Domino/Notes to Google Apps for Education. 40,000+ users in all. Nearly done.

          Don't really like the interface, but was not my decision. Would have gone with MS 365 if it had been. I have Outlook sort of working with Google Apps mail, but still am unable to access our Global Address Book, which Google says I should be able to do. A work in progress for me to hopefully accomplish.

          Putting Office docs/files into and out of Google Docs usually results in formatting being all screwed up by Google, and the e-mail GUI is just plain crappy. Can not sort individual columns in Gmail, as is the case for BOTH Outlook & Lotus Notes, as well as other features that just aren't in Gmail.

          Our migration from Lotus to Google went quite well, actually. Calendars, messages and other items were switched almost without any issues. And those that did come up were easily addressed.

          But...still would have preferred to go to MS 365, because all of our users use MS Office, and it just does not play well with Google Apps for Education. Oh well...................
          • Spyware

            That's 40,000+ people being spyed on by Google. When will people learn, all Google apps and services have one goal. Help Google build their profiles on the users. Nothing is free in this world and Google makes a lot of money selling ads to those profiles.
          • Are you kidding me?

            There is a difference in Google monitoring the browsing habits of people and placing those results in a profiling database to greater leverage adspace and define how they want to business, and an encrypted paid service like Google Apps for Business. They do not monitor anything people with paid accounts do, EXCEPT perhaps browsing habits based on traffic. Additionally, Google Apps for Business do not use adspace. That would alienate their client base entirely and be business inappropriate. Take off the tinfoil hat, and think it through logically.
    • Email Snobs

      I keep an AOL account around just for use with email snobs. Don't make me use it!
      • Cute...

        AlmostOnLine certainly has a very very long history.

        I'd certainly see a emailname at aol dot com as professional!

        • Than what?

          email name at businessesdomainname dot com? That seems silly to me.