Windows Insider

3 Reasons Office 365 Could Ultimately Fail

I spent a recent weekend setting up Office 365 for a friend's new business. The experience was far from comforting. My friend, Dan, isn't a deeply technical person. By day, he's an architect. By night, he's applying his creativity toward a new business framing concert art.

Dan came to me hoping to solve what seemed like a simple problem: He needed e-mail services that were something more than your average Gmail account. He just didn't know what that "more" was.

After hours of effort -- spread across the entirety of a weekend -- I was successful in migrating Dan at Gmail onto Dan at Office 365. Yet while the migration was ultimately successful, the challenges I faced in getting him there have me concerned about the potential for failure of Office 365.

While setting up his account -- and repeatedly comforting him that "everything will soon be all right" -- I considered three reasons why Office 365 could ultimately fail. I share them with you here in the hopes that it doesn't.

Reason No. 1: A disconnect from the needs of everyday people.

Looking through, any IT professional can plainly see the services it offers. Yet even at their most simplified, those services remain impenetrable to the non-technologist. My friend frames concert art; some might say brilliantly so. His business needs are, in his words, "e-mail" and "I'm not sure what else."

Finding the meaning behind Dan's requirements is fundamentally important to the success of Office 365. Microsoft's marketing still misses that mark. Until Microsoft can crystalize how Office 365 solves actual problems of everyday people, its services may never break out of society's techno-centric minority. Suggestion: Simplify.

Reason No. 2: The perception that you still need an IT professional. Cloud computing consumer offerings purport to deliver IT services without the need for IT professionals. That egalitarianism is a good thing.

But an ever-more technological world requires technologies that "just work." My friend Dan is a framer, not an IT professional. His business succeeds when he frames, not when he's working with technology.

My hours of effort in migrating DNS MX and NS records, linking connected accounts, configuring policies with Windows PowerShell, and everything else a new P1 plan requires didn't bring Dan comfort. Office 365 must streamline these barriers to entry or find itself strangled by the reach of the world's IT professionals.

Reason No. 3: Embarrassingly poor online support. The least-expensive Office 365 plans offer online support only. That online-only support could be sufficient if its forums were easy to navigate and answers easy to find. Unfortunately, neither is the case.

Office 365 online support is insufficient to the point of being embarrassing. Finding answers to even the simplest of problems is impossible at worst and a time-intensive chore at best. Resources are spread among multiple locations, with no unified "How-To" structure readily available (or easily found).

Responses to questions appear scripted, and are generally unhelpful or non-direct. Official responses in forums are often merely repeated when clarification is requested. Surprisingly, cross-platform compatibility issues are often ignored or minimized.

Take for example the Office 365 Community's "Top Topic" (as of this writing) titled "Android Connectivity." This topic outlines a compatibility issue for mobile devices without documenting a complete solution. After two weeks, 15 comments and no official response, that's a concerning lapse for a "top" topic. It suggests even less support for less-common problems.

An online service like Office 365 is only as good as its support. It is indeed an impressive platform for business. Microsoft's next task lies in helping the world figure it out.

About the Author

Greg Shields is a senior partner and principal technologist with Concentrated Technology. He also serves as a contributing editor and columnist for TechNet Magazine and Redmond magazine, and is a highly sought-after and top-ranked speaker for live and recorded events. Greg can be found at numerous IT conferences such as TechEd, MMS and VMworld, among others, and has served as conference chair for 1105 Media’s TechMentor Conference since 2005. Greg has been a multiple recipient of both the Microsoft Most Valuable Professional and VMware vExpert award.

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Reader Comments:

Sat, Mar 23, 2013 Roy Morris Conway, Arkansas USA

I am highly disappointed. I have a week to go on my "Free 30 day trial" so I decided to purchase on a brand new Samsung Ativ 500. First the software said to un-install old office. Then when I went to install new Office it would start the process then go over to the desktop and just do nothing. Did this 10 times. Called customer service, they gave me another number to call, called them and they gave me another number to call. Called that number and after 47 minutes it hung me up. I call that number back right away and it said they were closed for the day. Now I have a report and power point I wanted to do this weekend and I have nothing. I am LIVID to say the least. One thing I did not have trouble with was Microsoft taking my $100.

Thu, Mar 14, 2013 Dylan Sandhurst

Reason Four - Office365 does not integrate with Windows 8. YOu need another liveID account. Fine, two accounts to do one thing. HOWEVER... ...try setting up your email or using any apps - the email defaults to LiveID (rather than the preferred O365 account) but the apps all need you to sign in again with the LiveID - the Office365 IS NOT LINKED in. Useless. But more an issue with the requirement to use a Windows LiveID with Windows 8 to get full functionality. For SMEs moving to Win8 this is a nightmare. SSO in an AD environment does NOT facilitate this. I now have to create for my 450 users an individual live account for them all! Which I then cannot manage. grrr.

Thu, Aug 30, 2012 tom acito cincinnati

I am in the " you can't be serious" phase. I started with an expiring small business live account that I attempted to switch over to a office 365 account.. after actually losing 4 days worth of email from a bad switch from I now have a non functional domain name in Hotmail/live/outlook whatever it's called where my skydrive is trapped and the account cannot receive email. and a similarly named office 365 account that is hobbled after 3 weeks and a multitude of multi hour long tech support calls. I am ready to scream. I am comp tia certified for A+ and NET + and it's just an oozing mess to switch not to mention, it's NOT COMPATIBLE as a base account on windows 8. WTF! this debacle of office 365 incompatibility continues on the new windowsphone as well...

Tue, Aug 14, 2012

I think this comes down to you doing work for a friend... The reason he is asking you is due to him not being able to, so what you should be thinking is does he really need Office 365 and if the answer is still yes he should be paying someone to do it rather than relying on freebies

Tue, Aug 14, 2012

I don't agree with the authors comments.. Poor reasoning

Wed, Apr 18, 2012

You need to find a good partner to help you. We provide information that makes the process simple. We have a lot of organization where the administrative assistant run the office 365 and windows Intune. Environment. Once we have a customer migrated, the service just works. The problem you have is that there is too much information on how to do it, and you get confused as to what you really need to do

Mon, Apr 16, 2012

I echo the writer's comments. I run a small healthcare VC fund with 5 employees. I am a closet techie, but not a hack. We just migrated from BPOS to Office365. I had really high hopes for 365, and though many have been met, the farthest from the mark is ease of use. I would like to suggest 365 as a solution for our start ups, and did with BPOS, but the issues we've had with diverse user systems (Mac and Windows) and configuring them correctly has been crazy. It has taken hours of work. Until MSFT can make it as easy as drop box or box net, they won't be able to convert the small and middle market. The potential is there, but the set up experience is a big hurdle.

Thu, Apr 12, 2012 Jay Ritchie Chicago, IL

#1. It seems this is a criticism of the website. Try this - how do you know what Google product you want that compares to Office 365 if you're a non-techie? Do you even know to search for Google Apps? If you somehow find Google Apps for Business website, is it any more clearer? Office 365 is a suite of products and I think the website does a pretty good job of getting a small customer to the point of just trying it. #2 - Agree with Jarrod above - if you're doing things with PS for a P1 user, you're doing something wrong or something that wouldn't be any easier (if even possible) on other cloud platforms #3 If you want professional support, go to an E plan. When O365 was released, Google didn't offer phone support, so the P plan was designed to match this.

Sun, Apr 8, 2012 DanburyIT St Paul, MN

We've had a great time converting clients from gmail to O365. We can do an entire company setup and migration in about an hour or two...we use MigrationWiz and bypass Microsoft support (and tools) altogether.

Fri, Apr 6, 2012 Jarrod Higgins

Reason #1: completely agree. Microsoft always seems like they want to talk above people's head. They need to present reasons (in plain english) why a business should choose O365 over Google Apps. Reason #2: Disagree. I'm currently using a P1 plan and though it wasn't as smooth a setup as Google Apps it certainly wasn't a pain. Using power shell to setup policies sounds like you just made it harder on yourself. Reason #3 COMPLETELY AGREE the support is a joke. Unacceptable for a paid product.

Wed, Apr 4, 2012

Reason #3 touches on a general impression I have of Microsoft. Microsoft publishes more documentation than anyone, but it is heavy on theory and light on practice. I am always reminded of my college textbooks that would explain the theory and then say "proof is left to the reader."

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