In response to David Gewirtz's move to Office 365

David Gewirtz recently wrote an article over at ZDNet called "My big email switch: Why I picked Office 365 over Google Apps". I thought many people may have the same questions and thoughts that David worked through so I thought I'd join the conversation. 

It's a good article (and project) that he obviously put a lot of time and thought into. Obviously he can do whatever he'd like but I think David should have gone the other direction for multiple reasons.

Why Google? 

He lays the most obvious reason out himself.

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.

David can sense that his collaboration with his partner organizations would improve but it's impossible for a traditional Office user to really understand how much these interactions can improve. There is no comprable experience in the world of desktop apps.

Yes, it would be much easier to "connect into files" on Google Docs if you were already authenticated, but that's the tip of the iceberg. A "file" is a thing. A Google Doc (and Sheet, Slide, Form or Drawing) is a "place" - it has a uniform resource locator (aka a URL). A "thing" has to be passed around individually; only one person can have the "thing" at once - this is why we have version nightmares and dozens of copies of important files. A "place" is somewhere we can all be together and thanks to the modern Internet, we can all be at this same place regardless of our physical location or what particular device we happen to have handy.

Think about how much easier it is to share something interesting from a web site relative to a Word document - it's night and day; there is no comparison. It's hard to collaborate on an Excel file with 5 people who work in the same office! But you shared 1000x that amount of data with 1200 of your closest friends without even trying. The World Wide Web was LITERALLY invented to make sharing and collaborating on content easier.  Don't believe me? Let the man tell you himself.



As a full time Google Apps user David would have been able to flip dozens of workflows, large and small, completely on their head. It is not at all uncommon for dozens of tasks that used to take the better part of a week to be knocked out in minutes.

Why Office 365? 

David's #1 reason he wants to use Microsoft's "cloud" service = Microsoft's desktop software. Pretty sneaky Microsoft.

It's time to stop using Outlook and we'll get to that shortly. But, while you should, you don't need to. Google Apps Sync for Microsoft Outlook sets up in minutes and works great.

Outlook has given us some great memories but it's time to say goodbye: 

• Outlook runs on a single hard disk (or SSD if you're lucky!) in your computer. 1 disk. Gmail runs on multiple data centers simultaneously. 

• Backing up Outlook is your problem. It's taken care of in Gmail. 

• Restoring Outlook is your loved one's problem as you become increasingly frustrated. (It took David 13 days to fix his Exchange/Outlook environment several years back)

• Outlook for iOS = no. Outlook for Android = no. Outlook for Mac = please in the name of all things holy don't do that.

• You need to install and maintain Outlook on any computer you want to use it on. Gmail works on any computer at any time. Never say "I wish I had my work computer" ever again; any computer is your computer. Cloud Computing makes us less reliant on computers; it's one of the ironies of this paradigm shift. 

• Outlook breaks. Sometimes it's fixable; often times you have to reinstall it. Reinstalling takes hours, if you're lucky. 

"I like Outlook better" is something you hear pretty often (and there is the sync connector for those who won't or can't change). But Gmail is more robust, faster, and more mobile. It works better - it is a utility, a tool. What you're really saying is "you're comfortable with Outlook" and that's understandable. Remember when you told everyone who would listen you'd never get rid of your Blackberry? Then you wondered how in the world you used that piece of junk for so long? Similar situation. It's time. 

David also mentions he needs PowerPoint and that "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." Why? Office 2010 isn't going to stop working anytime soon; the amount of Office 2003 still out there is amazing. Office 2010 is good to go for at least 3 more years. Office is a perpetual license, check the box and move on. The costs David lays out are off as Office has already been purchased. Office 365 = $360 per year based on the article. Google Apps = $100 ($50 per person). $260 is a good chunk of change to hold onto.

Multiple Google Accounts

David's biggest complaint here is that he can't take all of his personal Gmail stuff into his work account. I think this is a good thing. Why would you want to? He probably doesn't have all his personal stuff in his current Exchange account ... otherwise why the Gmail account?

To some of the specific points raised by the author.

• I would share my personal calendar into my work account. 2 minutes to do including logging into the account. David mentions he uses Google Calendar as his primary calendar (I think) - in this case I would just export the Gmail calendar from the personal account and import it into the work account. This takes 5 minutes. This has the added benefit of allowing for professional meeting invites in and out of the account as the professional identity hardworker@mycompany.com vs. justsomedude@gmail.com - this also applies to chat, Google Docs, etc. 

• David also mentions chat contacts. Chat will figure out who you email with and add them in chat if they're available or you can send the invite to force it ... you want to chat, send the invite. A few seconds maybe. Just add them when you want to chat, you don't need to figure it all out at once. Just do it as you work.  

• David talks about Google Voice a bit but I'm not sure I follow. You can move a Google Voice number from one account to another. If I used it as a personal and work #, I'd keep it associated with my personal account ... you'll be you for life, work identities change. 

• David says "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." I think this is wrong. Many people have personal Gmail accounts that they want to keep personal. They have Apps accounts for work. I don't see how this is different than how he has it set up now. Google tools are useful in personal and work life but we don't necessarily want all that data smashed together. 

It's at the end where David absolutely loses me.

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.

David didn't want to use Google Apps for Business because everyone he works with uses Google Apps for Business. That's one I haven't heard before.

I've made many assumptions in this overview, some of them are undoubtedly wrong, but if you're a person using lots of Google services working with a lot of other people using a lot of Google services ... well, the squeaky wheel uses Office 365.

8/27/2014 Update: apparently David agreed: http://www.zdnet.com/why-i-bit-the-bullet-and-finally-switched-from-outlook-to-gmail-7000032179/