You're probably expecting me to write a scathing exposé on how I've come to dislike Google Apps. That's quite far from the truth behind why we left Google. There is a lot more to the story than meets the eye. It goes way farther than just a decision based on boxes checked off on a spec sheet. After more than one month since making the move to Office 365 full time, I can comfortably say we made the right decision as a company.

And of anyone who can make an honest dissection of Google Apps against Office 365, I'd say I'm as well suited as anyone in the IT blogosphere to be passing such critical judgement. Notwithstanding my own personal usage of Gmail since 2005 and Google Apps for my IT company since early 2010, I've likewise been both a Google Apps Certified Trainer and Google Apps Certified Deployment Specialist for years now. And I've personally been involved in Google Apps transitions for numerous small and large organizations in both the public and private sectors. So to say that I've been deeply invested in Google-ism for some time now is an understatement.

I've written some in-depth reviews of Google Apps and Office 365 separately in the past, and get frequent mail from both of them based on how I pitted one suite against the other in this category or that aspect. And while I'm not saying for a moment that I take back any of the statements I made in those pieces, I do honestly believe that "dogfooding" a given platform into your day to day business needs is the truest way to form the most accurate opinion of a product.

Surely, all of the monthly consulting time I spend helping other clients with their Office 365 and Google Apps installations gives me a raw insight with which to form solid opinions upon. But eating the dogfood you're peddling to clients? That puts your own skin in the game in ways that doesn't compare otherwise.

So that was my intended experiment of sorts. After spending nearly four years on Google Apps, learning its every nook and crevice, I threw an audible at my staff and told them we were transitioning to Office 365 by Thanksgiving 2013. And that's exactly what we did. By Turkey Day, we were fully transitioned off Google Apps and drinking Redmond's email kool-aid primetime.

The last month and a few days have been an interesting ride. From UI shock during the first week or so, down to natural comfort at this point. Here's the skinny on what insight we've learned about leaving Google behind.

Forget Spec Sheets: This is a Battle of the Ecosystems

For anyone that has cold-called me asking about whether they should go Google or Microsoft for email, they know full well I don't tote the corporate line that either company wishes. The big players in the cloud email arena tend to have pitched their tents in one camp or another. They're either Microsoft Office 365 only, or conversely, stuck in Google Apps-ville. Unlike car dealers, where buyers stepping through the doors know exactly what they're going to hear when they walk in, clients looking for honest direction for their email and UC needs want more than marketing drivel.

The battle between Microsoft and Google goes a lot further than who has bigger inboxes, more mobile apps, or whatever new whizbang feature can generate easy buzz. I've carefully learned that this is more-so a battle of the ecosystems at this point. Who's got the all-encompassing platform that is looking to solve business needs the way your company views them? Who's going to solve your email problems today, but offer you a segway to cloud document storage & unified communications & etc tomorrow?

That's the question companies and organizations should be asking themselves. Because it's the realization I've come to after our two-feet-first jump onto Office 365 a little more than a month ago. Google Apps isn't a bad platform by any means. In fact, it's pretty darn good. But in my eyes, when you view both suites as the sum of their individual parts, as a collective experience, Office 365 takes the upper hand. And I'll explain why in detail.

At face value, Google's core Apps offerings in the form of Gmail, Docs/Drive, Sites, and Hangouts are fairly solid offerings. But as a collective whole, they lack a certain polish. That x-factor which takes a platform from just good or great, to excellent. Google's way is just that -- the Google way or the highway.

This in-or-out dilemma exists in many facets in the Google Apps realm. For example, using Google's Hangouts functionality for video and voice chat requires you to have a Google+ account activated. It's basically a Google account that is opted into Google's social network, Google+.

I have nothing against Google+ as I find it vibrantly different and more gratifying than Facebook these days, but forcing your meeting participants to all have Google+ enabled on top of having Google accounts as well? That's more than a bit self serving if you ask me. In contrast, Micrososft's Lync doesn't require any of this for me to initiate meetings with external users. As long as I myself have a paid account for Lync, I can invite whoever I want (up to 250 of them, in fact) no matter if they ever had an Office 365 or Microsoft account in their life.

Google plays the same card on the way they treat Microsoft Office users. Sure, you can upload anything you want into Google Drive and store it to your heart's content -- but good luck trying to edit or collaborate on those documents in a web browser. Google will gladly convert those files into Google Docs, and force you to play the Docs-vs-Office juggling act in your file storage needs. We did it for years, but I had enough.

The same goes for Google's half-hearted support for Microsoft Outlook. I know very well that Google has been advertising their half baked Google Apps Sync for Outlook tool for years. I'm far from an Outlook desktop app lover, as I use Outlook Web App nearly 99 percent of the time on Office 365, but I know many companies live or die by it. You don't want me to describe the feelings that users of this plugin which have been conveyed to me. The comments I've heard in the field would make a Comedy Central comedian blush.

Not to mention that Google spent the better part of 2013 lambasting Microsoft for making changes to how Office installs via Click-to-Run, saying that their Sync tool wouldn't be compatible with the new 2013 edition of Office for this reason. And then they made a 180 degree about face come November 2013 and released an edition of Sync that actually does work with Click-to-Run after all. I guess enough enterprise customers poured their lungs out at Google support and they eventually kowtowed.

Mind you, Outlook extensions of all sorts were functional with Outlook 2013 leagues before Google got their act together, including ACT! by Sage and ESET NOD32 Antivirus, to name a few. But I digress.

At face value, Google claims their Sync for Outlook tool is the perfect holdover for those who wish to use Outlook on Google Apps. In reality, I know this is far from the case. Of the numerous companies I've moved to Google Apps who are reliant on Outlook and use this tool, not one has been completely satisfied with the product due to bugs, glitches, and other oddities we run into all the time. Google should be advertising their Sync tool as sorta works, sorta doesn't. (Image Source: Google)

If you take a look at the ecosystem that Office 365 affords, it's breadth and approach is different in every conceivable way. Google believes in an all-you-can-eat pricing approach; Microsoft believes in paying for only what you need. Google's Drive cloud storage app treats Office files like the plague; Microsoft believes you should be able to work on the desktop or in the browser as you choose. Google's Hangouts tool gets first class treatment in Google branded products only (Chrome, Android); Microsoft offers Lync capability nearly ubiquitously on almost every device and OS on the market.

The same can be said about Google's approach to an industry compliance necessity for the medical sector, HIPAA, which has begun affecting our company due to our status as a business associate for healthcare customers. While Office 365 has supported full HIPAA compliance since its early days, Google has been a holdout until Sep of last year. Mind you, Sep 23 was the deadline under the HITECH Act amendment that stated health organizations had to be in full compliance by that date. In short, too little too late from Google's end -- they shouldn't be surprised that healthcare is staying far away from their platform.

It goes without saying, then, that if you are solely chasing feature matrices when making your decision between Google and Microsoft, you're only revealing half the story. An email platform in 2013 is not just an inbox; it's a unified communications tool that will make or break the way your organization works with the rest of the world.

SharePoint vs Google Drive: Who's Hosting your Cloud File Server?

Up until Office 365, my company was living a double life in terms of its document storage needs. We had an office NAS box (a nice QNAP TS-239 Pro II+, which we still use for bare metal client PC backups) that was storing traditional Office documents for some aspects of our day to day needs. And then Google Drive, which was the hub for collaborative authoring that we needed for our onsite tech support team and training team.

But this duality was causing more confusion and headache as time went on. Was something stored on the NAS or Drive? Was it a Word document that we converted to Docs? Which copy was the master at that point? I call this mess the "Docs v Office juggling nightmare" and I was sick of it. Google Docs is awesome for sharing and collaborating, but Google forces you into using their online file format; it's an all or nothing proposition.

So we ate our own dogfood once again after the 365 move, and converted our two-pronged data storage approach into a single unified SharePoint "file server in the cloud." It's definitely not pick-up-and-play like Google Drive/Docs is, but the time invested in building out document libraries with proper permissions was well worth it.

First of all, Google's thinking around how they allocate and manage storage in Drive has always driven my clients and myself nuts. Instead of being able to dole out storage space that is meant for separated, shared purposes -- like shared folders that represent root file shares of a traditional server -- they force storage to be tied to someone's Google account. That is usually an admin, a lead user, or someone similar. In theory, it works decently, but you run into traps easily.

For example, if someone creates a root level folder outside the scope of a folder already owned and controlled by an account that has extra storage allocated to it, then anything placed inside that new directory will be counted against the respective owner's storage quota. So as your organization grows, and people start using Drive the way that it was meant to be used -- in a laissez faire kind of way -- then you better hope all your users have a good handle on how Google Drive storage allocation works behind the scenes. If not, you'll be falling into such "who's storage are we using?" holes. The K-12 sector taking up Apps in droves is running into these headaches head on, I'm hearing.

SharePoint Online and SkyDrive Pro in Office 365 skip that mess altogether. If you're working in true shared folders, or document libraries as SharePoint calls them, you're working off pooled storage space available to all permitted users in your domain. By default, all E-level Office 365 plans (the only ones we recommend to clients) come with a 10GB base of shared space, with an extra 500MB of space added for each extra paid SharePoint user on your account. So if you are a company with 15 users and have SharePoint rights, you have 17.5GB of SharePoint space for your document libraries in the cloud. Simple as that.

SharePoint Online works hand in hand with SkyDrive Pro and allows me to securely sync our company's entire cloud file shares to my laptop, which is locally secured by BitLocker in case of theft or loss. I have access to the exact same files on my desktop SSD (right side) as I do in the cloud and via web browser (left side). This is the cloud file storage nirvana I dreamt of with Google Drive starting back in 2012, but Google has thus far failed to deliver. As much as they claim otherwise, I can't live in a Microsoft Office-less world ... yet.

And SkyDrive Pro offers a completely distinct 25GB of space per person for their personal data storage needs. Think of it as a My Docs in the Cloud. It works more akin to the way Google Drive does, but for good reason: that space is ONLY meant for you, not to be shared with others in a file share environment. You can freely share docs out via Office 2013 or in Office Web Apps, but this is meant to be done on a limited basis with a few people. More formal sharing should be handled in document libraries in SharePoint sites.

Specs aside, have we lost any functionality on SharePoint? Not one bit. Usage of SharePoint and SkyDrive Pro is better in our organization now than under Google Apps on Drive previously, mostly due to there being no more need to juggle between what files can be Office documents and which ones have to be Google Docs. All of our Office documents (Word, Excel, PowerPoint, OneNote) can be shared and worked on offline and online equally well. Office Web Apps don't have 100 percent feature fidelity yet, but they're on-par with what Google Docs offered for getting work done quick and dirty in a web browser.

And we're going to be leveraging SkyDrive Pro heavily soon with a new way of digital work orders that we are going to roll out for our techs which mixes SDP along with Excel, topped off with our new chosen endpoint devices: Lenovo Thinkpad X230 Tablets. A technician's workhorse laptop hybrid with full stylus-driven tablet functionality. Initial tests have been working out real well for us.

I plan on writing a longer expose on how we made the move to SharePoint, but at face value, we are enjoying SharePoint Online due to the numerous benefits it has provided. We erased duplicity headaches, streamlined our file storage into one platform, and combined what Google Sites and Drive had to offer in combination with what SharePoint now does in one single interface.

I'm not saying Google Drive is a bad product in any way. But it didn't solve our needs the way I had expected it to back when Google rolled out it in 2012. After loathing SharePoint for how complex it has always been, the new 2013 iteration is a refreshing product that when coupled with Office 365 is a no-brainer option for moving your file server to the cloud. And clients who we have been moving to SharePoint Online have been equally impressed.

Lync is for the Workplace; Hangouts is for Friends

Another huge tool we've grasped onto quickly is Lync for our intra-company communication needs. Our office manager is pinging our techs in the field with info and vice versa; I'm able to discuss problems with my staff over IM or free voice calls even in areas where cell signal is dead. And as I wrote about last year already, we ditched GoToMeeting a while ago in lieu of Lync for our online conferencing needs.

The battle of the ecosystems between Google and Microsoft is on full display in the video/voice/IM arena. Google is trying its best to transition a muddled 3-pronged offering landscape on its end into one single system. But for all their efforts, I'm still just as confused with their intentions because as of Jan 2014, we still have three distinct options for unified communications in the land of Google Apps.

Google Talk, the previous go-to option for intra-Google communication via IM and voice chat still exists in some remnants. My Google Apps Gmail account still offers it, for example. And then you have Google Voice, which has been Google's POTS-enabled offering for more than a few years now for softphone telephone needs. But some of that functionality is being tangled into Google Hangouts, which is their bona-fide video and voice chat platform going forward.

If you asked me what Google's UC strategy looks like in one sentence, I wouldn't be able to answer you succinctly. It's because at Google it feels like the left arm is on a different page than the right leg, and so you get the picture. They have a fractured array of offerings that all do a little something different, and many have overlapping features -- and so the Google Apps proposition is confounded by too many choices, none of which present a single solid solution for what companies are yearning for in unified communications.

Stop the madness. Since our move to Office 365, Lync has been the answer to our frustrations. I don't have to juggle between Talk and Hangouts for my conferencing and IM needs. I have one single app, one single set of functions to learn, and a tool which arguably ties into the rest of Office 365 very nicely.

Whereas Google relies on Hangouts, a tool that is for all intents and purposes a function deeply rooted in their social network Google+, Lync is an all-inclusive app that can stand on its own via various Lync desktop/mobile apps, but is also present in some facets in the web browser as well. As a heavy user of Outlook Web App, I can see presence information for my staff in emails that they send me, and the same goes for docs on SharePoint document libraries. It seems that I'm never more than a click away from starting a conversation over IM or voice with someone on Lync, reducing the barriers to getting the answers I need fast.

My favorite aspect of Lync has to be the universal access I have to the app no matter what device I am on. If I start a Lync conversation on my laptop at the office, I can head out on an emergency client call and continue the conversation on my smartphone (I use a Lumia 925 now) without a hitch. This was only possible on Google Apps when I was within the web browser and using an Android phone previously. Google doesn't offer much of anything for Windows Phones; but Microsoft offers almost everything for Google's and Apple's platforms. Who's playing favorites in reality?

Google Hangouts limits you to measly 10 person meetings. Lync allows us to max out at 250 participants, and we can even tie into fancy Lync Room Systems as shown above for formal conference style gatherings. It doesn't cost any extra than the price of an Office 365 E1 account or higher. A darn good deal in my eyes -- especially if you can ditch GoToMeeting/Webex altogether. (Image Source: TechNet)

Yes, I will admit Microsoft's approach to Lync for the Mac desktop platform is still a bit pitiful, as numerous features in the Windows version are not available on the Mac side yet. And I called Microsoft out on it in a previous post. But from everything I'm hearing in my circles, Office 2014 for Mac (as we expect it to be called) will bring Lync and the rest of Office up to speed with what Windows users are afforded.

Another area that I am anticipating to launch any month now is Microsoft's first-party Lync enterprise voice offering that will enable us to use regular SIP desk phones with the Lync service for full telephone capabilities. While we are using RingCentral right now without a hitch and love it, I think Lync-hosted cloud voice is the holy grail of unifying communications for my small business. And judging from the number of people that email me asking about this functionality, I'm not alone in my wants. Seeing what Microsoft reps stated last May about this coming-soon feature, all signs are pointing to an inevitable 2014 launch.

Is Lync perfect? Not by a long shot. Mac support is still dodgy and behind the Windows client. I deal with off and on bouts of messages that refuse to reach my staff with errors pointing to behind-the-scenes goofy Lync network issues. And Microsoft needs to vastly improve the Outlook Web App integration of Lync to the level of what Google Talk has in Google Apps; the rudimentary support enabled right now is a bit of a disgrace compared to what it could offer users like me.

But unlike Google, which continues to distribute its efforts between three hobbled apps (Hangouts, Talk, Voice), Microsoft is 100 percent committed to building out Lync. And that's a ride I am comfortable sticking around for, as it's serving us well so far.

The Truth Behind Google Apps and HIPAA Compliance

One of the primary reasons I decided to take a swim in Office 365 land is due to Google's lackluster adoption of HIPAA compliance for their suite. If all you use Google Apps for is email and document storage, Google's got you covered.

But is your medical organization interested in building out an internal wiki or intranet on Google Sites? Sorry, that's not allowed under their HIPAA usage policy. Or are you looking to perhaps do some video conferencing with Hangouts between other physicians or even patients? It's a hot and burgeoning sub-sector of healthcare called telemedicine, but don't plan on using Google Apps's Hangouts for it -- Google says you must keep Google+ shut down in your Apps domain to stay compliant with HIPAA. The list of dont's 'doesn't end there.

I reached out to Google Enterprise Support to get some clarification on what they meant by requiring us to have core services enabled to keep HIPAA compliance, and a Patrick from their department replied to me via email:

My apologies for the misunderstanding, you are indeed correct. If you are under a BAA, you can turn off non-core services but core services such as Gmail, Drive, Contracts etc must remain turned on.

This is another unpleasant necessity for organizations that want to, for example, merely enable Google Drive for cloud document sharing between staff members but do not wish for Gmail to be turned on. Coming from the public education sector before going on my own, I know full well that the picking and choosing of services in Google Apps is a highly desired function and one of the biggest selling points for Apps to begin with. So what the heck, Google?

Don't get me wrong. HIPAA compliance with Google is now fully possible, but only if you're willing to bow down to Google's backwards requirements of what you can and can't use on their suite.

I had full HIPAA compliance with Office 365 on the first day we went live, and I didn't have to sacrifice SharePoint, Lync, SkyDrive Pro, or any of the other value-added benefits that come with the ecosystem. Seeing that Google Apps has been on the market for over 3 years more than Office 365, I find it quite unacceptable for Google to come to the game with one hand tied behind its back, and late at that.

I'm calling Google out because I know they can do much better than what they are advertising now as HIPAA compliance with Apps. And until that happens, I'm refusing to recommend Apps for any clients even remotely associated with the healthcare industry so they don't have to go through the pains I described.

Office 365: Still Not Perfect, But A Value Proposition Better than Apps

There's a lot of things I love about Google Apps. Its release schedule for new features is blazing fast; much quicker than what Office 365 has. Google has a knack for releasing innovative features, even if they don't fill needs gaps for what I am yearning for. And their all-you-can-eat price point of $50/year USD for Apps is a hard price point to beat even for Office 365.

But I've come to learn that wading through marketing speak and engrossing yourself in a product as massive as an email suite is the only way to truly uncover what each platform has to offer. No amount of consulting for clients could give me the insight on these two suites as actually using them day to day has afforded me, in direct knowledge and purpose-driven understanding.

I don't regret for a minute the four years we spent on Google Apps. It's a solid, good product. It's second only to Office 365 in my eyes. Hosted Exchange, Lotus, Groupwise, and all the other second-tier options are far behind in contrast to these two suites in pricing, bang for the buck, and security/compliance standards. But Microsoft's value proposition is one which I can relate to better.

Splitting the apps apart, you will likely find areas where Google's respective apps do a better job at this or that. But an email platform investment is a two-foot dive into an all-encompassing experience that goes beyond the inbox today moreso than ever before. And that's where I find Microsoft to be winning the ecosystem battle: in providing an immersive experience that doesn't have rough edges drowning in engineering experimentation.

At the end of the day, I have a tech consulting business to run. While I enjoy fiddling with the ins and outs of features for my customer needs, when I come back after a ten hour day onsite, the last thing I want to be doing is bending over backwards to work the way a suite expects me to. And that is increasingly what I was feeling with Google Apps. Google's vision of cloud computing is markedly different than most others', and if you can't abide by their rules, you will pay the price in lost time and functionality.

My customers have learned this very fact with the Google Apps Sync for Outlook tool. I've experienced this with our frustrations with Drive/Docs. And most recently, Google's HIPAA compliance stance leaves me scratching my head. So for the time being, we've bid Google farewell for our own internal needs.

Will we return someday? I hope so. But for now, Office 365 is doing a darn good job and I'm more than pleased, even if Microsoft has its own kinks to work out with Lync and Outlook Web App. I've brought my company onboard for the ecosystem, not purely for an email inbox. If you can step back and objectively compare email platforms in the same manner, you may come to a very different conclusion as to what vendor you should be sleeping with tonight.