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Microsoft and the Bridge between Consumers and the Enterprise: The Continued Struggles of Windows 8 and Office 365
Josh Greenbaum
JAN 16, 2013 11:25 AM
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The ability of Microsoft to ride the consumer/IT juggernaut to glory rests on a large combination of factors, but two of the most important are the success of Windows 8 and Office 365. And while Microsoft is generally to be credited for doing better than expected in both domains, there are serious flaws and omissions in their strategies for both that threaten the company’s run for glory.

Both are related to how well Microsoft positions itself as the bridge between the consumer and the enterprise world –  a manifest destiny it cannot afford to flub. Both are also eminently fixable, but the fact that these problems exist in the middle of Microsoft’s biggest bet since the launch of Windows in 1986 speaks to the continuing gaps in how the company is executing on CEO Steve Ballmer’s vision.

Let’s start with Microsoft’s Windows 8 problem. First, I’m happy to report that it’s not a technical one. I upgraded from Windows 7 to Windows 8 on my Lenovo X220 laptop about three weeks ago, and the operating system has been largely perfect. Lenovo’s attempts to add its own upgrades to my PC were the only screw-up, adding some unwelcome drama to an otherwise trouble-free upgrade.

I’m also happy to report that the touchscreen laptop experience with Windows 8 is as impressive as I had expected. (This review couldn't be more wrong, IMO).  In the office, I run Windows 8 in extended screen mode, with my “desktop” apps running on my 24-inch monitor and my touchscreen apps running on the laptop’s screen. On the road, I swipe back and forth between desktop and touch mode as needed, and the intuitiveness of the interaction between keyboard and touchscreen increases with every day. This multi-mode interaction model will be very appealing in the enterprise, which is why I think Microsoft is in position about to teach Apple a lesson about human/computer interfaces and user engagement – having the two modes in a single machine is an enormous productivity boost, and makes my iPad and my single mode PCs look old and backwards by comparison.

But while early adopters like me are generally enjoying the touch experience, Microsoft is having some problems in how it is marketing Windows 8 that I think will pose problems for consumer adoption, and hence for Microsoft’s goal of copying Apple by using massive consumer demand to land a beachhead in the enterprise for Windows 8’s unique touch-enabled user experience.

The main problem with marketing Windows 8 is this: someone forgot to brand the touch experience and highlight its unique value-add to Windows 8. There’s plenty of advertising that’s showing off how Windows 8 works as a touch-based OS, particularly on the Surface. But in one big arena, branding the hybrid touch/desktop experience, Microsoft has flopped. And nowhere is that more apparent than in the home courts of the big box retailers that drive consumer and small business buying on a massive scale.

Last Sunday the big box retailers in my area – Fry’s, Best Buy, Office Depot, Office Max, and Staples – all ran ads hawking various PCs running Windows 8. What was clear from scanning these ads is that it’s not clear which PCs are touch-enabled and which are not. And with on average three-fourths of the PCs in the Sunday ads being not touch-enabled, the consumer’s ability to identify Windows 8 with a next-generation touch experience is confused by this mix of touch and non-touch enable PCs. And the lack of visual cues to help consumers understand what they are looking at in a Windows PC ad makes that confusion a big problem.

The confusion that drives this – to touch or not to touch – speaks to the larger issue of whether the only touch-worthy Windows 8 experience should come from a Surface, or how much Microsoft and its hardware partners should be promoting Windows 8 touch on laptops at all. In my opinion Microsoft fails if touch remains largely synonymous with Surface, and does not become de rigeur for laptops too. And right now it’s heading towards fail mode.

In an attempt to make things clearer – which has actually made things worse – some of the retailers, Fry’s, Best Buy, Office Depot, and Office Max, created their own (lousy-looking) touch icons to layer over their ads, while Staples just threw a little “touch screen” text overlay on the screen shots of its touch-enabled PCs. This means the consumer browsing for a new PC has to hunt for a visual cue, unique to each retailer, in order to align their buying experience with the opportunity to buy a new, touch-enabled PC. While the retailers’ ratio of touch to non-touch PCs may make sense in terms of the current demand and price curve (touch-enabled laptops are typically $300 more than a non-touch laptop), the lack of clarity makes the shopping experience surrounding Windows 8 more than a little confusing.

This is in sharp contrast to what happens when prospective buyers look at an iPad or Android tablet or Surface, or an Apple computer or laptop, for that matter. There is absolutely no doubt that a consumer looking at an ad for any of those device types knows instantly what they are getting – touch-enabled tablet and non-touch computer (okay, there’s touchpad on Apple laptops, but that’s not what we are talking about here.) Whereas the same consumer, looking at a Windows PC ad, has to wonder, as I do every time, whether what I’m looking includes a touch screen. Despite these icons – which are of course not specific to Windows 8 and could be used to designate any old touch-based device – the shopper looking for a touch-enabled Windows 8 machine is going to have look harder than he or she should.

Why this discourse on the branding and iconography of Windows 8? Because it’s part of the reason Microsoft isn’t doing as well as it could with Windows 8. Not only does Microsoft need consumers to buy Windows 8 because it’s touch-enabled (as opposed to being a somewhat better-performing upgrade to Windows 7), Ballmer and Co. also want to emulate Apple and use consumer pull to drive Windows 8 touch into the enterprise. This dual purpose means that the initial consumer experience has to be as unambiguous as possible: if consumers can’t easily and readily identify Windows 8 with a touch-enabled user experience, then they’re likely to see Windows 8 as just another upgrade with a cost and learning curve that isn’t necessarily justified if touch isn’t part of the reason to buy. And thereupon Microsoft fails.

Sure, they can just by a Surface, and have the unambiguous experience, but to be frank, if the Surface remains the major touch-based system for Windows 8, then Microsoft has also failed. There is simply no way that Microsoft can make Windows 8 touch successful without its hardware partners. And the big box ad/icon problem is indicative of how confusing the buying experience can be – and by contrast how simple it is to know what you’re looking at when you glance at an ad for an iOs or Android device. If Microsoft can’t brand the touch experience, and brand it visually so that consumers equate Windows 8 with touch, then the battle is lost before it can begin.

Most importantly, losing the consumer battle means the enterprise market – which needs a compelling reason to forestall or leapfrog its XP to Windows 7 upgrade plans in favor of a touch-enabled hardware refresh to Window 8 -- will never ever happen for Windows 8. This, I am sure, would be a missed opportunity from which Microsoft might never recover.

Which brings us to the other case of consumer/enterprise disconnect way, way over in Office 365 land. Office 365 is another important leg to the Microsoft strategy: offer a great online experience for its flagship Office productivity tools that can blunt the impact of Google’s burgeoning online apps strategy and drive acceptance of Microsoft as a major cloud services player with a serious consumer/enterprise bridge offering.

Success in consumer-class cloud services has its own special set of criteria, which boils down to providing a simple way for a customer to sign up, pay for, and start using the service with little or no human-to-human interaction. This self-service model has become the most basic component of any online service, and while the task of linking up an existing desktop Outlook environment to Office 365 is non-trivial, by and large Office 365 fits the online self-service model well.

With one enormous omission – self-service upgrades. Microsoft’s Office 365 team has, probably inadvertently, completely messed up what should be as simple as anything – and everything – in the online world: upgrading a customers’ class of service. Instead, early adopters of Office 365, of which I am one, have found ourselves in a veritable online services Catch-22 that is a perfect example of how not to succeed in the cloud.

The sad story goes like this. Anyone who signed up to Office 365 a year ago, including me, had only one option that made any sense to a single-user operation: the service level known as P1, “P” as in professional. It was very well-priced, $6/month, and for that price we were given phone support – an absolute necessity in those early teething phases of use. Problems like the aforementioned issue about running desktop Outlook in synch with Office 365 took a lot of phone support to solve, in particular because whatever online documentation and community support was available simply didn’t, couldn’t provide the required level of assistance. I also used phone support to deal with the complexities of linking my email, hosted by a separate hosting service, to Office 365. In both cases I need some serious phone support to resolve the problems.

So when I was informed late last year by Office 365 that the terms of service for P1 would be changed and that phone support would no longer be offered, I immediately looked into upgrading my service. And there it was, the E1 service level: $8/month with phone support. Not a problem – I can afford another $24 a year, and I figure one phone call to tech support will make the extra $2/month worth it. So I set out to upgrade the service, and then the fun began.

First, while E1 was listed as an available plan on the home page for Office 365, when I went to upgrade from within my account E1 wasn’t available. Instead, my only option was Professional Plus, listed at $15/month. As this was more than double what I was currently paying, and almost double what I had expected to be paying with E1, I wasn’t thrilled. I clicked the “learn more” tab and then found out that while Professional Plus was listed in the next page for $12/month, the landing page made it seem that it didn’t include Office 365, if that was even possible.

Confused? Me too. So I called sales support to find out how to get E1. And then the enormity of Microsoft’s consumer cloud disconnect became evident.

Sales support told me that I couldn’t actually upgrade to E1, but would have to cancel my P1 account and sign up for a new E1 account. This, of course, would mean backing up all my Outlook data, killing the old account, reloading the data into the new account, resetting all the different devices that connect to my Office 365 Exchange server (five), and reconfiguring the email forwarding set up with my ISP. Reloading the data would also probably change my desktop Outlook configuration, and, considering my track record with the interplay between desktop Office, Office 365, and my ISP, this alone could be a couple of days work.

“But all I want is phone support,” I told the earnest young man trying to make sense of this mess for me. “I’m running my business on Office 365, I don’t want to troll for answers in some online forum. Is there any way to get some phone support?” And, just to make it clear that I believe that you get what you pay for, I threw in the kicker:  “I’m willing to pay.”

The answer was simple: Not without upgrading – I mean migrating – to a new plan.

So I tried a different tack: Is there any way to automate that migration, are there any tools available to do this seamlessly? That elicited an answer that actually made me smile, however ridiculous it was.

“You need to call Office 365 tech support and ask them,” I was told.

But wait – I don’t have phone support, remember? I told the sales support guy. “Well, the best I can suggest is that you sign up for E1 before you upgrade, and then you can phone tech support under the E1 plan.”

Thanks, and good night.

Actually, before I said good night he told me an important fact that no consumer should ever ever ever give a damn about: the reason I just can’t upgrade to E1 is that P1 services are on a different set of servers than E1, and, well, that means that the consumer has to manually move the data from one system to another. In reality, of course, the technical details of migrating a service from one set of servers to another is a red herring: this really means that Microsoft couldn’t be arsed, to use my favorite Briticism for willful negligence, about automating this migration.

The fact that this is required in order for the consumer to pay the service provider more money for more service just adds insult to injury. Ugh.

So here I sit, an otherwise happy consumer, credit card in hand, just trying to make sure he has phone support to keep his business running. And there sits Microsoft Office 365, sincerely trying to be a consumer-grade service provider, having despite its best efforts found a way to deprive itself of revenue while making the most simple and basic of service requirements not just hard, but impossible and infuriating.

I’ll end here by saying that I still think Microsoft has more than a fighting chance of making mincemeat of the touch-based market by offering a dual-mode touch/desktop experience, and I still think Office 365 has a chance to help define Microsoft as a bona fide cloud services vendor. But forgetting to brand the touch experience in the minds of consumers is going to make finding the path to the Microsoft touch experience much harder than it has to be. And making service changes that require customers to jump through flaming hoops to keep up is going to make Microsoft look oafish at a time when it desperately needs to look cool and slick.

The moral of the story is this: the two problems I’ve written about here are things Microsoft shouldn’t have gotten wrong in the first place. Microsoft knows more about branding than most companies, and should have figured out the touch branding problem from the get-go. And, with the online services market over a decade old, there’s no excuse for messing up the P1 to E1 transition, other than someone got sloppy at a time when sloppiness can’t be allowed.  If this was the first time Microsoft thought so inside the box it boxed itself in, I would be less annoyed. But this example of how to be tone deaf to consumer requirements is unfortunately not the first that I've felt the need to write about.

Luckily this is Microsoft, and if I’ve learned one thing in the 25 years or so I’ve following these guys, they do second and third acts better than most. So, stay tuned for version two of the Windows 8 touch experience, there will be stickers and logos and lots of swag too. And stay tuned for the Office 365 simple service upgrade service, seamless and painless. I’m sure it will make its debut any day now.

It’s not like they really have a choice.

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