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.


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.

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.