The United States Air Force recently announced that the $1 billion you were hoping would be spent on something useful (or not at all) has been lost forever to Oracle and Computer Sciences Corp. in the wake of a failed attempt to upgrade the Air Force’s back office.

While there are usually as many reasons for project failure as there are stars in the sky, I think I found a smoking gun buried in some of the language used by the Air Force to announce what was supposed to be a major improvement in modernizing the military and controlling costs that turned into yet another major setback. What emerges is a cautionary tale about how enterprise software is sold and marketed, particularly by a company like Oracle that has make the ready integration of disparate enterprise software products a “feature” honored more in the breach than not.

The original award had the lofty goal of upgrading over 400 legacy systems in order better support how the Air Force goes to war. Considering what is at stake – making sure the 750,000 men and women in the Air Force are well supported and provisioned – the goals of the project were laudable.

Also laudable was the focus on COTS – commercial, off-the-shelf software – which the U.S. government has been using more and more to lower overall IT costs and promote standards across the board. Which is why Oracle 11i was chosen to be the enterprise software anchor of the project.

So, how did the Air Force, Oracle, and CSC blow it? The how is a little tricky, but the what – $1 billion in tax dollars shot to hell – pretty much points to the usual combination of bad planning, scope creep, cost-overruns, and other classic mistakes that you’d think would be avoidable in the 21^st century.

Indeed, it’s obvious that this was a typical big bang project gone sour… But with a twist.

The twist can be found in the following statement, made in September, 2006 when the award was made: “As a result of this selection, CSC will use processes within the Oracle 11i product suite to support all logistics functions including product lifecycle management, advanced planning and scheduling, repair and maintenance, and distribution and transportation. The integrated suite (my emphasis) will replace more than 400 legacy systems.”

Oracle 11i, , a.k.a E-Business Suite, in 2006 was itself integrated, but it had relatively limited capabilities in such key areas as PLM, planning and scheduling, and transportation, among others. Fair enough – apparently the Air Force procurement office decided that these functions were good enough for the government, and Oracle got the nod.

But the functionality inherent in EBS at the time wasn’t good enough for Oracle, and in fact much of the functionality that was essential to the Air Force project was already or about to be the subject of an acquisition spree by Oracle. Transportation management in the form of G-Log had been acquired in 2005, and Demantra’s planning software was acquired three months before the Air Force award was announced. PLM market leader Agile was acquired in 2007.

So, what was the “integrated suite” the Air Force thought it was buying in 2006, and what was the integrated suite that Oracle and CSC were trying to implement starting in 2008 (when the requirements blueprint was to have been finished)? It’s really hard to tell without an actual copy of the award document, but any decent requirements blueprint for a client like the Air Force would have stipulated the very best that the vendor could provide (that’s how these things are written – no one wants to implement mediocrity, right?). That in turn would have meant that by 2008 it was apparent that key functionality like PLM, planning, and transportation management should be based on Oracle’s newly acquired products, and not the core of Oracle 11i.

The problem is that the use of these or any other pieces of acquired software not part of E-Business Suite would have meant that the solution the Air Force was thinking was “integrated”, and consisted of “processes” that lived within Oracle 11i in reality consisted of a bunch of recently acquired products in desperate need of data and process integration. And while Oracle has tried to make application integration a virtue, and has thrown unsuccessful products like Application Integration Architecture at the problem it has created by buying dozens of incompatible products over the last 17 years, the fact remains that integrating Oracle’s applications are still complicated, costly, and a major bottleneck for its customers’ implementation plans.

Also note that it was during this timeframe that Oracle Fusion hove into view, and in fact at the time of the award Oracle was preparing to claim that it was “halfway to Fusion”, as well as promising an upgrade to Oracle 11i and a comprehensive Fusion integration strategy in the ensuing year. So you can probably add a new version of EBS, some Fusion apps and middleware to the blueprint as it was being readied to be part of a billion dollar barrel of pork.

So, while the evidence is purely circumstantial, the fact that the Air Force is basically writing off the project and dooming our flyers and support personnel to living in a legacy environment for the conceivable future points to a failure that very likely included the effects of “portfolio creep” on the part of the vendor as it added new products to the mix and further complicated an already complex “big bang”.

While any project failure of this magnitude has plenty of blame to go around – CSC and the Air Force need to be taken to the woodshed too – it’s clear that if the Air Force thought it was getting an integrated suite in 2006, it picked the wrong vendor. And at each milestone, 2008 when the blueprint was finished, and 2012 when the plug was pulled, Oracle’s portfolio only got more complicated, and the integration challenge more complex.

The moral of the story, to be fair, isn’t just about Oracle. It’s about every software vendor’s promise of integration – to its own products and those of its competitors and partners: Integration is hard, and is a common and costly point of failure. The tendency is to over-promise, and the temptation to do so in order to win a chunk of a billion dollar job is too tempting.

This moral extends to the customer as well – we all like to believe what we want to hear, and surely the Air Force, struggling to overcome a massive legacy quagmire, was happy to believe that it was buying an integrated suite with integrated processes that spanned logistics, PLM, planning, and the like when it was buying something else.

And while we’re at it let’s call out CSC, which has some duty – legal, moral, or probably both – to protect the clientele that funds the bulk of its revenue – U.S. taxpayers – from its own stupid mistakes. How this project got to be a total failure is clearly as much or more about CSC than it is about Oracle. Bad software and naïve customers alone can’t kill a project, you need bad consultants too.

And we’re all stuck paying the bill.

Jeff Immelt of GE has the biggest calling card I’ve ever seen, and he wasn’t adverse to flaunting it on stage late last month at GE Software’s coming out party. Flanked by a 12 foot tall GEnx jet aircraft engine, Immelt took to the stage to make clear that GE’s next big bet would be on the what I’ve called the sensor revolution, what others call the internet of things, and what GE calls the industrial internet.

The risk that this bet will fail to make an impact on GE and its customers is largely zero –the company’s smart devices are everywhere, from GEnx engines loaded with sensors measuring temperature, airflow, and turbine spin rates to massive locomotive engines collecting accelerometer and location data to hospital equipment sending out patient and equipment status updates to consumer appliances providing energy consumption data. These sensors are everywhere – numbering literally in the billions. Which is why this sensor data revolution is, in my opinion, orders of magnitude more valuable than the click-stream and location data that is currently being mined from consumer devices and web-based customer interactions and hyped as the primary source of the so-called big data revolution.

The big data revolution is so-called for the simple reason that data is as data does, which is not much. The key to this revolution, and GE’s bet on the industrial internet, isn’t just about creating and gathering data, it’s about analyzing and operationalizing it. And it’s at the analytics level that GE will see its greatest challenge. More on the big analytics  issue in a moment.

But first, let’s make it clear that these issues – sensor data and analytics — are, of course, much larger than just GE (which, at $140 billion in revenues, is saying a lot). GE has plenty of company in this industrial internet, with the likes of Siemens,  Johnson Controls, and Honeywell, to name just a few, all scrambling to sell what is estimated as $14 billion in sensors this year.

It’s also much bigger than GE because there are an almost infinite number of markets that could become part of this industrial internet revolution: Automotive, communications, security, utilities, aerospace and defense, and imaging are just some of the areas where sensors are generating unimaginably large quantities of data that need to be turned into analytical gold. (A quick aside: what do you call this quantity of data? Someone at the GE event referred to this much data as a “hellabyte”, which is a helluva great word, IMO).

This depth and breadth makes the worthiness of GE’s efforts indisputable. Immelt made a great case for the butterfly effect of using the industrial internet to drive a next wave of optimization and efficiency in a broad range of industries – like aviation, rail, healthcare, power generation and oil and gas exploration and refining – as well as industrial disciplines like material science. A one percent saving – which Immelt postulated would be readily available by  optimizing the industrial internet – could result in annual savings of $30 billion in aviation fuel, $2 billion in railroad productivity, and $63 billion in  healthcare productivity, among others.  Not a bad set of goals overall.

As long as the effort to capture the industrial internet’s data as well as analyze it are combined, or at least engaged simultaneously, these goals are likely to catalyze a whole host of companies to get on the bandwagon with GE. Exactly how those billion dollar goals are actually going to be realized will take more than one GE Software event to answer, though the gaggle of Silicon Valley VCs and assorted digerati assembled in the shadow of the GEnx engine was a good start.

But only a start. The fact that the enterprise software industry was largely absent from the event, both on the podium and in the audience, points very much to where GE needs to take its message next. And what the big analytics challenge looks like to GE’s customers.

The enterprise connection is essential to GE’s effort’s because, rather than being a new new thing, the race to tame the industrial internet is a movie we in the enterprise software market have been standing in line to watch for years. The manufacturing shop floor has been full of industrial internets based on control standards like SCADA or DNC/CNC for decades, and companies like OSIsoft have been effectively capturing and unleashing the industrial internet in industries like refining, chemical manufacturing, and paper products for over 30 years. Railroad cars and jet aircraft are already bristling with sensors, and hospitals are replete with machinery annoying patients and providers with their lonely and much too audible digital heartbeats. Industrial-strength data has been around for a long time.

But while these data have been well-analyzed within the context of their domains of origin, moving these data to the next analytical level is the real challenge. The shop floor controller data stream already informs a manager when something is wrong with a vital piece of equipment and needs remediation, just as the GEnx can send data on the resonant frequency of every critical bearing in the engine in order to detect whether the bearings are wearing out and need replacing. But that’s barely scratching the analytical – and operational – surface when it comes to GE’s dreams of the industrial internet.

The big payoff comes from taking those data outside their domains of origin and using them for a higher purpose. That’s where the shop floor control data is used in combination with external demand data to optimize the supply chain and reconfigure the shop floor for a rush job  in real time. And where the hospital analyzes the data stream from its infusion pumps  and uses it to both plan maintenance as well as inform epidemiological studies analyzing patient outcomes based on infusion data. Or when an airline analyzes  bearing frequency data reported in flight  from the GEnx to not only schedule maintenance  but also check on parts availability and schedule the mechanics needed to do the job.

These analytical examples require a blending of enterprise software – ERP, materials management, maintenance management, human resource management, and the like – with the sensor data that makes up GE’s industrial internet. That analytical cross-pollination yields information significantly greater than the sum of its parts, and begins to explain where Immelt gets a one percent improvement in operations that can yield billions in cost savings and other benefits.

GE Software definitely has plans to work with the enterprise software gang, some of whom, like SAP, are waking up to the fact that they need to be part of the sensor revolution as well. And much of what enterprise software has been doing in terms of data management, integration, and analysis will apply quite nicely to the problem of taking those data from the industrial internet and turning them into more than just a bunch of reports. I’m looking forward to hearing how GE plans to move in the direction of the enterprise software market, just as I am looking forward to seeing more enterprise software companies take note of the opportunities that await them and their customers in the industrial internet.

With GE staffing up its new software team in San Ramon, CA, we can expect to hear a lot more about the industrial internet and GE Software going forward. The efficiencies that Immelt spoke about aren’t pie in the sky – while the exact numbers are estimates, the order of magnitude of change that is possible is irrefutable. Also irrefutable is the complexity of blending the world of the industrial internet – which is really many many different data ecosystems as opposed to a single, unified system – with the world of enterprise data.

But the journey to the industrial internet is a worthy one, and GE Software’s ability to catalyze a much-needed revolution in big analytics is even more worthy. Immelt wasn’t just showing off a cool example of a smart device that can also deliver 70,000 pounds of thrust, he was really about the future of the enterprise and enterprise software.  It’s a journey that’s been a long long time in coming, and if, GE can pull it off, that journey is about to reach cruising altitude.

The latest debacle at Hewlett-Packard involving the allegations of accounting wrong-doing at Autonomy make for a particularly sticky wicket for CEO Meg Whitman. While there have been some attempts to blame her predecessor, Léo Apotheker, for the decision to buy Autonomy, it’s impossible for Whitman to avoid taking ultimate responsibility for the deal. And when the dust finally settles on this latest in a series of miss-steps at HP, the question of what can be done to save this storied Silicon Valley icon from itself will be harder and harder to answer.

Part of the problem is that even if Autonomy had knocked it out of the park, instead of fouling out, it never would have turned HP around. Not even close. The fact that it’s now another big HP deal gone bad just adds to the sense that all we can do is watch a Greek tragedy unfolding on stage before our eyes.

Whitman’s blame problem starts with the fact that the Autonomy deal was on the table even before Apotheker showed up, and became a component in the strategic planning for the company pretty much from day one of Apotheker’s short reign. Considering the board’s role during the interregnum between Mark Hurd’s departure and Apotheker’s appointment, the board, of which Whitman was a member, had to have been considering, if not vetting, the Autonomy deal during that period. So rather than blame Apotheker, Whitman has only to look to the HP board – of which she was a member – to find where the blame game starts, and stops.

The allegations of financial impropriety on the part of Autonomy have also to be taken into context in light of the failure of two other major acquisitions, EDS and Palm. With former CEO Mike Lynch making a spirited and public defense of his former company and its accounting, the fact the HP’s track record with big M&A is so poor weighs heavily in Lynch’s favor. Certainly, given that track record, it’s easier to think that HP and its board screwed up yet again rather than to think that the many audit firms and other companies and individuals charged with making sure the Autonomy acquisition was on the up and up were all simultaneously asleep at the wheel. Same with Lynch – I’d rather bet on HP’s board being wrong that on Lynch being foolish enough to publicly challenge allegations of financial misconduct that he knew were true. On the contrary : At this point I give him the benefit of the doubt, the circumstantial evidence indicts Whitman and the HP board more than it does Lynch and Autonomy.

It’s pretty clear that buying Autonomy at all  was a misstep, certainly in light of the fact that, at $10.3 billion, HP wasn’t likely to be able to make another big software acquisition unless its financial position improved significantly. Ironically, rather than being the architect of the Autonomy deal, Apotheker was initially lukewarm to it. And while the exact reasons for his initial ambivalence are not known to me, it’s clear that, regardless of the innate qualities of the deal, Autonomy wasn’t going to be big enough – in terms of strategic potential and revenue contribution – to move the needle at HP far enough to make the Apotheker era a success.

Part of the problem with Autonomy was that its revenues were simply too small to have the impact Apotheker needed to have. At the time the acquisition was on the table, Autonomy had just turned in fiscal 2010 revenues of $870 million. Not a bad number, but not enough for an acquiring company pulling in $120 billion a year. In fact, in order for HP to really start turning the corner, particularly in light of the fall-off in its printing, server, and PC businesses, and the on-going failure-to-execute problems with its services business, Apotheker needed to figure out how to add more than the equivalent of Autonomy’s annual revenue every month in order to do the job he was hired to do.

Hampering that target was the fact that the other M&A assets at HP that were supposed to be pitching in were in fact horribly behind in their own plans. EDS and Palm, which together were acquired for over $14 billion in 2008 and 2010 respectively, were underperforming at a depressing rate. While there was much optimistic talk by Apotheker and others about how Palm’s WebOS was going to be part of a unifying operating system fabric for HP’s PC, printer, and enterprise business, behind the scenes Palm was screwing up the development of the Touchpad so badly that it launched the clunky and inelegant tablet in July 2011 – in the face of a sleek iPad II launch three months earlier  – with little software and no real business plan. The result was an unmitigated disaster, a product with a great OS and an industrial, throwback feel that couldn’t run Netflix, read a PDF document or a Kindle book, or even surf the web very well (it runs an open source version of WebKit that performed only adequately at best.)

I was told later that year that a post-hoc analysis showed that HP would have had to spend hundreds of millions on WebOS just to get it to where it had a snowball’s chance in hell of competing with Apple. And considering that the Touchpad was not even a close competitor to the iPad, and had limited developer traction,  killing Palm and the WebOS market (okay, it was put out to pasture as freeware, pretty much the same thing) turned out to be the only merciful option.

Meanwhile, EDS kept missing its numbers mostly because the acquisition that was supposed to lead HP into the promised land of strategic enterprise consulting services was stuck in the past selling massive non-strategic outsourcing deals, or trying to. But because these deals were so huge, and so driven by commodity pricing considerations, EDS was losing enough of them every quarter – and not gaining the more coveted strategic deals in competition against the likes of IBM Global Services and Accenture – that it kept missing its numbers. And when you miss a couple of big deals in a quarter, you miss big. And EDS’ ability to help fix HP turned into another albatross draped around Apotheker’s neck.

It’s important to see that these two big deals were harbingers for the Autonomy fiasco, and not just because HP eventually wrote off $885 million of the $1.2 billion it paid for Palm and $8 billion of the $13.9 billion it paid for EDS. More importantly, in both cases, HP’s board, and its executive team, were simply unable to make these acquisitions effective, and integrated, parts of the company. The problems that led up to M&A failure being part of the HP Way were institutionalized before Apotheker showed up, and were so overwhelming that neither Apotheker in his year in office nor Whitman in her year of office could hope to have changed them.

The basic problem was – and remains — that there was no common culture, the HP Way being really many, different, and competing ways. The way of the servers, the way of the printers, the way of the PCs – it was almost comical how uncooperative these traditional HP business units could be with one another, much less with newly acquired assets. Of course, you can blame Mark Hurd for much of that anti-culture: he ran HP like a loose confederation of medieval city-states, each one competing with each other for the attention of King Mark, whose main concern was making his numbers, not building synergy or cooperation, and, God forbid, vision. The board, in case it’s not obvious, condoned this operating model as a way to keep investors on board.

King Mark also created a relatively hostile workplace, one that shocked employees from acquired companies who were used to a minimum of respect and a decent place to work. Not only did HP embrace a dehumanizing cubicle farm model housed in depressingly cavernous warehouse/offices, it provided no WiFi in its headquarters, no subsidized lunches for its employees, no regular janitorial services (this is not a joke – employees had to empty their own waste baskets!), and an amazing arcane accounting and HR system that demoralized the old-timers who stuck it out and horrified the newcomers who showed up on the M&A train.

Not surprisingly, employees of both EDS and Palm – and, later, Autonomy – made it clear they really didn’t feel they were part of HP. They continued to use eds.com and palm.com domains for their email accounts long after the acquisitions, and they acted as though the best thing for all concerned was to remain apart from the rest of HP. Having witnessed this studied apartness firsthand, and having seen the results of the internecine fighting inside the rest of HP, all I can say is that Autonomy was doomed from the start.

So, whether there were financial improprieties or not is pretty much immaterial in terms of judging whether buying Autonomy was a good idea or not. For Autonomy to succeed it would have had to buck the dominant anti-culture and pull off an amazing coup-de-finance that would have seen its revenues somehow driving a huge surge in new business for HP. That fact that it would have had to go against the real HP Way to do so made it look highly unlikely. The fact it would have to do that in a company that had just fired its second CEO in two years and had one of the most demoralized workforces in Silicon Valley – imagine the meet and greet with the new colleagues following Apotheker’s departure and Whitman’s ascension – was ludicrous.

Which brings us to the final, ultimate question: can anything be done to save this company? The answer is probably yes, as long as preserving shareholder equity is not an issue. But considering this is a public corporation, with a board that at least understands, if not practices, the concept of fiduciary responsibility, I see no way to make the HP of today greater than the sum of its parts. That ship sailed a long time ago….

…and, as befitting the Greek tragedy that is Hewlett-Packard, sank in the wine dark sea.

The backstory to the launch of Windows 8, Windows 8 Phone, the Surface and all the other recent announcements from Microsoft is more than just a little interesting for Microsoft Dynamics, the enterprise software sub-division of Microsoft and one of the smallest pieces in the software and hardware company’s vast portfolio.

Indeed, the backstory for Dynamics is really no backstory at all. Dynamics is in the driver’s seat for Microsoft’s efforts to realize one of the  biggest technologies bets in Microsoft’s or any other technology company’s history. If Dynamics can pull it off, the trickle-up success across Microsoft will provide an unexpected element of prescience and justification to the oft-questioned decision to buy Great Plains and Navision and launch the company’s enterprise software aspirations.

Just to keep the pressure up, we’re talking more than just any old technology bet. This one is personal: Microsoft CEO Steve Ballmer is literally betting his company and his reputation as an executive and a visionary on a slew of new products and services that spans the entire Microsoft product line, the consumer and enterprise markets, the worlds of on-premise and on-demand software, the desktop and the mobile device, social computing and batch processing, the new and the old.

And it’s largely up to Dynamics to make sense of it all.

Because beneath the hubbub of massive product launches and increasingly cool looking consumer technology is what amounts to a complete re-positioning of Microsoft at the convergence of the enterprise and the consumer market. If Ballmer’s right the bet will vault Microsoft forward as a major player in myriad new markets that looked out of reach for the company only a few years ago. Think Lou Gerstner and IBM, circa 1994. And if Ballmer’s wrong, at least Meg Whitman at HP will have someone to commiserate with.

Dynamics’ mandate is anything but simple: take several dozen major brands – from Surface to Windows 8 to Azure to Xbox to Skype to SharePoint to Dynamics AX, to name just a few – and show how the sum of the parts is greater than the whole. This is what Dynamics head Kirill Tatarinov and his team call  the “unifying fabric” of the new Microsoft. And considering how hard it has been in the past to coalesce Microsoft’s different divisions around a crisp, unified message that is meaningful across so many different products lines and to many different stakeholders – customers, partners, developers, integrators – the task in front of Tatarinov and his team is one of Herculean proportions. Complete with some stables to muck out and a monster or two to slay.

Part of what makes Dynamics’ – and Microsoft’s – task so daunting is the number of moving parts, the myriad products and services of the new Microsoft, that must be corralled and coordinated into an attainable reality for both existing and new customers. That means coming up with a well-constructed set of applications and services that respond to the needs and aspirations of both the company’s enterprise and its consumer customers.

The total palette that Dynamics has to work with is seemingly unending. When I tried to tally them up during a recent Dynamics analyst event I lost count at 25. So that you can join me and the Dynamics ecosystem in our sense of vertiginous wonder, here’s my short list:

And this is the short list. The real one is probably twice as long.

The other reason Dynamics’ labors promise to be so hard is that this unified fabric has to reach new markets, new customers, new channels and new geographies, and otherwise appeal to a global market in ways that haven’t traditionally been the purview of the “old” Microsoft. This means transcending the consumer and enterprise worlds, the large and small enterprise, the differences and similarities between vertical and horizontal industry requirements, and the on-premise and on-demand worlds.

Accordingly, the product mix isn’t the only thing that’s on the move. Much of the channels and markets strategy is starting to line up too: The company is aligning its Microsoft Consulting Services to weave more of the Dynamics message into its offering – Dynamics is the fastest growing component of MCS’ business, having doubled in size in the last year. Global systems integrators are being courted and the rest of the partner channel is now settling into the first full year of a massive restructuring process that has resulted in more accountability, greater scale within the partner community,  and a greater ability to meet this challenge. And the corporate sales team has become the vanguard of a strategic effort to push the new Microsoft into large, global accounts, with Dynamics in the cat-bird’s seat.

So, while it’s a  given the individual divisions – Windows, Server and Tools,  Online Services, Entertainment and Devices, and the rest of the Business Division that Dynamics is part of   – will cast Ballmer’s bet in light of their specific buyers and influencers, I believe that only Dynamics has the opportunity to show how a set of enterprise apps and services can light up the new and not so new offerings from each of these divisions, and show them, in all their glory, as the realization of Ballmer’s dreams for a new Microsoft.

If Dynamics is the unifying fabric, that fabric’s warp and weft comes from this rich palette of products, services, channels and markets that are now unfolding and will continue to unfold over the next two years. All that’s needed is a little creativity and vision, and a helluva big loom on which to weave that vision into reality.

Microsoft is clearly at a major inflection point, and how well it moves forward will be judged in large part by the functionality and, quick frankly, beauty, of the products and services that this loom can weave. Selling great consumer-only products won’t be enough to make Ballmer’s vision a reality, and it’s clear that the enterprise-only and converged enterprise/consumer markets will up to Dynamics to define. The sooner they can get started, the better.

Last year, when I attended Box.com’s BoxWorks conference for the first time, I was struck by the outrageous coolness emanating from founder and CEO Aaron Levie, as he stood on stage and ripped into Microsoft SharePoint as the embodiment of all that was evil and useless.

It made for great theatre, and outrageous coolness not only set the tone for the conference but also apparently heralded a great year for Box. Not only did the company garner some major investors – SAP, and Salesforce.com, among many others  – but it also began an amazing growth spurt that has catapulted Box out in front of a cloud apps market that is the most fast-moving sector of the tech industry this side of mobile.

And with great success has come something that is rare in dynamic startups run by charismatic, young founders: maturity. Levie is still funny and outrageous, and Box is still young and hip, but the company’s focus is clearly on making sure that growth and new markets are characterized by an astute reading of market forces, and not just on being cool and hip.

Hence, at BoxWorks 2012, instead of coming to bury SharePoint,  Levie came to praise it – or at least co-opt it. And instead of looking in the rear-view mirror at erstwhile partner Salesforce.com’s announcement of its own Box competitor, Chatterbox, or even giving passing mention to Microsoft’s Skydrive online storage and sync service, Box took the high road and made it clear that online storage and sync, the origins of Box, are no longer the differentiating characteristics of what Box is offering the market.

Instead, the message was clearly focused on the enterprise, and on issues that matter to enterprises  that are trying to fill in the white space in their business processes with not just storage and sync, but by also enabling real collaboration. All the while keeping an eye on security, regulatory compliance,  business process, and other features that distinguish enterprise solutions from their consumer counterparts.

I think the SharePoint shift characterizes the maturation of Box perfectly. SharePoint is the number one collaborative software product in the world, and that’s despite the best efforts of the dozens of collaboration vendors out there. There are  over 65,000  installations and over 125 million users in the world, according to published figures attributed to Microsoft,  so while in many ways SharePoint is truly the antithesis of Box, its pervasiveness is indisputable.

Hence Box’s co-opt model: instead of being vilified as the enemy, SharePoint is now a launch pad for Box. The main problems with SharePoint – nimble and agile are not words that come to mind when thinking about SharePoint – dovetail nicely with Box, where nimble and agile are the coin of the realm. As such we heard a number of users talk about letting SharePoint remain as the “system of record” in the enterprise and using Box as the “system of engagement” for enabling the kind of ad hoc collaboration and rapid enablement of workgroups that characterizes many high-value collaborative enterprise processes today.

The SharePoint shift reminds me of what another company founder, once known for his outrageous coolness and humor and now known for his love of sailing and hardware, told me about his own march  to maturity. The year was 1991, and his market was starting the maturation phase of an amazing upward march to fame and fortune. What was different with his approach in 1991 versus the 1980s, I asked him. Back in the ‘80s, he replied, he was the bad boy showing up on a motorcycle to change the world. Now, in 1991, he’s driving a sedan and wearing a suit, because in addition to changing the world he also wants to date the CEO’s daughter, and no grey-haired CEO is  going to let some punk on a Harley take out his little girl.

I don’t think Aaron Levie’s next step is to get a pair of wingtips and a wool suit, partly because I like his style, and partly because he’s already proving to be date-worthy, and the SharePoint shift is the perfect example. Seven years since its founding, Box has moved to its next phase, one in which it is balancing disruption with maturity, outrageousness with common sense. With style.  But in a sense Levie isn’t just trying to be hip and cool, he’s also trying to be meaningful to an IT/enterprise audience that wants a company like Box to be the bridge between enterprise functionality and consumer usability. And he’s pulling it off.

The takeaway from BoxWorks 2012 is that Box is becoming an enterprise player, moving beyond storage and sync into what I would like to call enterprise process optimization, except that sounds too heavy and slow.  But that’s really what Box is doing – filling in the white space in key processes that require sharing documents and collaborating , and in the process outmaneuvering the likes of SharePoint and Dropbox simultaneously. On the face of it, the differences are obvious – security, control, access, management, reporting are what makes Box the anti-Dropbox, and not just a competitor. And agility, flexibility, and usability, the hallmarks of a consumer product, make it the anti-SharePoint.

Levie was still outrageous and cool at BoxWorks 2012, even if he was delivering a more sober message about what really matters to the enterprise. Getting rid of SharePoint may not be top of mind, but enabling better control of enterprise information absolutely is. And if Box has to co-exist with SharePoint to make the point, so be it. Box.com doesn’t need to declare the end of SharePoint to succeed. Letting SharePoint be SharePoint seems to have been the much better strategy, and so far it’s working like a charm.

Several months into my experiment with Windows 8 on a Samsung Slate tablet, I now have answers to three important questions about the past, present and future of tablet computing, the so-called post-PC era. They’re questions worth asking, as the answers spell trouble for Apple and Android, and provide evidence of a new lease on life for the troubled PC, albeit a reincarnated convertible tablet/PC like my Slate.

At first blush, the questions may not be what have been bedeviling your IT or line of business decision-makers over the past few years. I admit I hadn’t thought about them or the market in quite that way either. But playing and working with Windows 8 has made me realize more than a few things about PCs, tablets, and what market leadership will mean in these two markets in coming years.

First questions first: Why does the native browser on the iPhone and iPad suck?

It’s well-known that the browser experience on these devices is less than sterling, and that’s without the problem of not supporting Flash. Having spent the last few months using a tablet running a full-fledged browser that is actually optimized to work as a browser (IE 10 on Windows 8, to be specific), I’ve finally figured out what must have been going on in Steve Job’s mind when he decided to limit Safari’s effectiveness on the iPad and iPhone.

Here goes: I’ve noticed over the last few months that the more I use the Slate the less I am tempted to bemoan the lack of native Windows 8 apps for the device (at last count, there were about 3000, compared to a jillion or two for iOS). In fact, it seems that I can pretty much do anything I need to do on my Slate that I would otherwise have done on my iPad.

That’s because it turns out that having  a great browser on the Slate means I can access virtually all the functionality I need from a web page, instead of running a specialized app to perform the task. No need for an app to check public transit, the weather, airplane schedules, my Amazon account, listen to  my local PBS station, check out Twitter, Box, or any other service I have a subscription to. I just point a browser – or better yet a bookmark – and away I go.

Amazingly simple, no? And it’s not like I’m out there mousing and keyboard my way back to the 20^th century either. I still having a full tablet user experience, swiping and pinching and otherwise doing that multi-touch thing that Apple pioneered.

Which leads me to the answer to my first question: the browser on Apple’s mobile devices sucks because if it didn’t, Apple wouldn’t have been able to build up its massive apps market. Okay, browser apps would have had to smart enough to do a better job of differentiating form factor (a la HTML5) between phone, tablet, and desktop, and it would have been really hard to monetize a browser-based tablet market the way the Apple Store has helped monetize the Apple Apps market. But fundamentally, if the iPhone and iPad really handled all web sites, supported Flash, and otherwise behaved as well as IE 10 on my Slate, Apple probably wouldn’t be dominating the mobile market through the closed iOS apps store the way it does today.

On to question two: Why is a device designed primarily for consumption the wrong device for the enterprise?

One of the truly great things about the Window 8 experience has been the ability to go back and forth between desktop and touch mode interchangeably. Some of this is a simple matter of using the touch screen to scroll up or down, zoom in and out, and otherwise navigate a document on the screen as part of the creative process. It almost sounds trivial, but it’s really useful. (Point in fact, ergonomics make this work only on a laptop/tablet device: the big touch screens on desktops PCs are too far away from the keyboard to be ergonomically useful.)

Importantly, some of the usability is very much non-trivial. The ability to use Office 2013 in full keyboard mode, typing my little heart out in Word 2013, and then go into tablet mode and navigate to a different desktop app or browse on the windows 8 Metro browser is something I can’t do on an iPad. Indeed, flitting back and forth between multi-touch tablet mode and heads-down keyboard mode turns out to be a significant usability improvement over either pure tablet or, more obviously, pure desktop. While Mac Air users have some of this ability, and those who are good at it can do some amazingly things with the touch pad, it’s not the same has having a full touch screen, not by a long shot.

This experience with the Slate has shown me that creating a demarcation line between consumption devices like the iPad and creation devices like the PC was a “mistake” for the enterprise that served Apple well in terms of creating a new cool device, a new market, and a new revenue stream. But it serves the enterprise much less well in terms of creating an artificial distinction where one need not exist at all. Windows 8 is going to prove that the enterprise customer can have both, and that, unlike two heads, two interaction modes really are better than one.

Which leads me to the final question: why is the real tablet revolution not about mobile at all?

Mobility is a convenience that we have come to take for granted, but we’ve had mobility for decades. I had a laptop in 1990, a cell phone in 1994:  that revolution went mainstream a long time ago. The real tablet revolution was about multi-touch, not mobility, and with that tactile experience we’ve discovered a new way to improve the user experience that, while it found its first mainstream expression on the tablet and smart phone, need not be limited to those devices.

Limited is the word, because the consumption-only, consumer-based design goal of the iPad placed limits on the degree of functionality that could be covered by an iPad app. As I have stated before, it’s somewhat fantastic to think that a CEO could run his or her business on an iPad – there’s just not enough functionality, firepower, or flexibility in this generation of tablet to make that a reality. It works great in sales, relatively good in retail, and self-service HR apps run well in an iPad too. But the artificial barrier of consumption-only means that there are limits, real limits, in what you can really do with these devices.

Indeed, this is where the real advantage of Windows 8 lies: it enables an existing desktop experience (and the megatons of enterprise software based on that experience) to live another day in a hybrid tablet, while enabling a new generation of software based on multi-touch creation and consumption to redefine the enterprise software experience.

Which is why I’m actually unimpressed with what I see in the Windows 8 store today, not because it’s relatively threadbare by the standards Apple and Android have set, but because I have yet to find that killer hybrid app that will bridge the creation/consumption divide and show just how valuable a hybrid user experience can be and how limited, by extension, the iPad user experience has been. But it’s coming, inevitably. Cloud pioneers like Box, and enterprise stalwarts like SAP, are looking seriously at Windows 8, and not because they want to make Microsoft happy. They see this experience and the devices it will support as a major new platform for functionality, and they’re voting with their development dollars to bring these new apps to market. Needless to say, but I’ll say it anyway, Microsoft Dynamics is also busy trying to make their offerings fit the “killer app” opportunity with Windows 8.

What does this mean for the enterprise going forward? The most important issue is that software development and the expectations that enterprises have for their user experiences need a quick refresh before too much is invested in buying iPads. It’s not enough to have your vendor promise a killer iPad app to satisfy your mobile user fan base. You should be demanding, and the vendors should be providing, multi-touch-based enterprise apps that can live in the mobile and the desktop world interchangeably. This creation/consumption experience, not the iPad’s consumption-only experience, is the future of computing in the enterprise.

I’ll end on a final note about the next generation of enterprise employee, as personified by my almost 9-year daughter, who so  far in her career has “worked” in Windows XP, Windows 7, iOS, and now Windows 8. Her go-to device today is the Slate, though from time to time she still plays Pet Hotel on the iPad (unless she’s online with a friend, in which case she’s on a PC). Though she doesn’t articulate her preferences with the historical perspective of her father, it’s clear these preferences are formed from the same observation: the Slate and Windows 8 offer all the best of a desktop experience, and all the best of a multi-touch tablet. In her vast experience, and mine –  and one day, I believe, yours –the iPad just doesn’t cut it anymore.

I was finally enlightened as to why I find Oracle’s annual customer event, Oracle Open World, to be an increasingly frustrating and largely unfulfilling experience. For the last few years I have been laboring under the misperception that one of the goals of this event was to inform the influencers about key Oracle technology and strategy developments, thus allowing us to go forth and advise and influence on what Oracle is up to.

This perception is wrong, I was told in no uncertain terms. And unfortunately for Oracle, its customers, and its ecosystem, that fact has a huge and potentially negative implication for Oracle’s position in the competitive market. (And, by way of an update, Mark Smith of Ventana research has another take on the negative side of vendor influencer programs.)

The bottom line is that OOW is a sales event, plain and simple. There is a secondary purpose relating to information and knowledge transfer, in the form of keynotes and overbooked sessions, but that’s really secondary. The goal is to pitch as much product to as many customers and to do it as efficiently as possible. (Efficiently for Oracle, not necessarily for customers and prospects). And Larry forbid, no real give and take, discourse, or critical discussion about product and market strategy should be allowed to take place.

The fact that OOW is primarily a sales event makes it no different than DreamForce, Sapphire, Convergence, or any other events by Oracle’s big competitors. But choosing not to influence the influencers makes OOW very different. And in the process significantly short-changes Oracle’s customers, prospects, and Oracle itself.

Here’s why. Oracle, more than most of its competitors, eschews releasing information in a regular cadence to the analysts, bloggers, and others who try to follow the company. During 2012 there have been exactly two events that I and most other influencers have been invited to, OOW and an analyst summit earlier in the year. The rest of the year Oracle has a particularly sparse public schedule when it comes to communicating its product strategies. Meanwhile, the above-mentioned competitors have multiple events that deliberately cater to the influencer community each year, and with each of them comes a rich schedule of 1:1 meetings with top executives.

So when OOW comes around, there’s a lot of pent up demand for information and access about what has happened during the course of the year, and that’s before the slurry of announcements that typify OOW and other like events. And herein lies Oracle’s big mistake.

By deliberately not creating an event that also caters to the influencers, Oracle misses a great opportunity to have its announcements and plans carefully analyzed, digested, and otherwise dissected by a broad set of influencers. That broad-based analysis, in turn, provides the basis for an intelligent and rich discussion on the pros and cons of one of the industry’s biggest companies, one that could help customers and prospects make wise choices about important issues in their IT and business strategy.

Of course, the customers will try to make these choices, just as we influencers will try to analyze what Oracle is up to, regardless of how restricted the information flow is. The issue is whether the influencers can do this with a level of detail and precision that will allow customers and prospects – our mutual customers, I might add – to make those wise choices. In the absence of good influencer analysis — what I think, somewhat self-servingly I’ll confess, is an important channel of information — the wisdom of these choices are limited. Limited, in the specific case of OOW, to what customers can glean from keynotes and standing room-only sessions where the amount of intelligent discourse and interaction are severely constrained.

What happens is that we influencers, many of whom, like me, consult to the Oracle user community (as well as many other user communities) find ourselves unable to make up for the information gap imposed by Oracle on its own customers. Sure we can schedule briefings with our end-user clients and discuss product choices and options with Oracle prospects and users, but there will always be an asterisk attached, one that clearly notes that this information is based on analyzing over-processed information from keynote addresses and canned presentations, and is not the result of a careful dissection and discussion with the vendor’s execs of the truth behind the marketing message.

Now, to be fair, Oracle did host three or four events during OOW  where one of their software execs sat in front of a group of analysts and answered questions. The time allotted was usually 30 minutes, and with a dozen or so influencers in attendance each time, you can rest assured that few questions were asked or answered. It may be that other groups – systems, database, etc. – were giving 1:1s to analysts who cover those areas, but the enterprise software gang was definitely not bothering to spend quality time with the influencers.

Should anyone but we self-serving and self-interested influencers care about this? If you think that Oracle – or any vendor – is going impartially tell you everything you need to know about your buying decisions, you needn’t worry. If you were able to get into all the sessions at OOW you wanted to attend, and ask all the questions you needed to, you can also not worry. And if you don’t need to do a real apples-to-apples comparison between what Oracle is offering and what its information-indulgent competitors are offering, relax and enjoy OOW.

The rest of you, please be patient if there are big gaps in our analyses, or if in a year or two it turns out that something Oracle promised doesn’t actually turn out exactly as you were told by Larry Ellison in his keynotes. We’re really trying to do our jobs well, as best we can. It’s just that Oracle would prefer that we not bother asking the hard questions, and, by extension, they’re saying you shouldn’t bother asking them too.

Do all companies build refrigerators when their product sets get too complex? That was the question I was asking myself as I sat in the audience during the partner keynote at Dreamforce last week, as a slide showing off the different parts of the company’s SaaS platform hove into view.

Memories of SAP’s NetWeaver danced in my brain as I quickly tallied the pieces, basically a what’s what of the Salesforce.com portfolio: a little Data.com, a little Force.com, some Site.com, Chatter, Heroku, a forthcoming identity management product…. Just like SAP lo those many years ago, Salesforce.com was building an edifice – make that an appliance – to the Gods of application and process integration.

Which was what the message to partners was all about: we need you to start integrating the growing portfolio of on-demand applications that our customers are deploying in a more comprehensive way in order to make sure they are reaping the benefits of the new on-demand world, integration-wise.

And just to hammer out the point, Pandora’s vice president of IT, Richard Rothschild, came on stage accompanied by a slide that itself harkened back to a previous era. Pandora, which boasts that it has essentially put all its key business processes in the cloud, has what can only be called a hodge-podge of largely disconnected, best of breed apps – Vana, Xactly, Brainshark, Cloud9, Data.com – that Rothschild admitted could be better integrated, if only someone could. Salesforce.com’s Ron Huddleston, the partner guy, agreed that this is job number one for his partners.

Welcome to the real enterprise, Salesforce.com.

I mean that seriously, by the way, without snark (though, like the NYT’s Gail Collins and her need to reference a certain dog-on-the-roof episode involving one of this year’s presidential candidates, I can’t help snarking just a little bit about the end of the end of software. I mean, doesn’t anyone notice that the end of software just keeps on needing more software to make it happen? I’m just saying…)

But more than anything, this first keynote of the conference brought home to me the realization that Salesforce.com has made some amazing strides in the platform war that is now engulfing the enterprise software market. And on paper and PowerPoint, they’re looking good.

I’ve written before about my three criteria for platform success in the 21^st century, and Salesforce.com is  definitely on track with all three: a strong tool set and platform for staging apps, a critical mass of developers to build them, and an online commercial website where partners can sell the apps. It’s clear that AppExchange, the commercial side of the equation, is happening, there are 1700 apps to date, up 27% from last year, and installs are currently running at 50,000 per month. Not shabby.

The partners cum-developers are clearly in critical mass mode: they filled the keynote room to overflow, and customer after customer told me they were looking at the AppEx partners to fill in the white space in the processes that intersect with Salesforce.com.

And the tools are there, or on the way. Hence the refrigerator pitch, though it was interestingly devoid of details on just how easy it will be to build an integration framework that could tie together a Pandora-like pure cloud environment or a more common hybrid cloud/on-premise environment. But heck, that’s really hard. It took SAP years to get NetWeaver out of slideware mode and into simple and easy to implement mode, despite all their efforts. So I don’t expect Saleforce.com to settle this issue in just one Dreamforce. It will take a while, no doubt.

Which is fine, because regardless of when all the products emerge to make the platform fully functional, the Salesforce.com fridge sets the customer base on the right track. It’s a stake in the ground to a customer base that is increasingly using Salesforce.com as its jumping off point into a fully-formed, enterprise-wide SaaS strategy – and, considering that very few of them look like Pandora, the need for Salesforce.com to be 100 percent ready with its platform play is still a way off. But the need for the customers to have a strong message about where to go when they’re ready to pull the trigger on an expanded platform view of SaaS is now, as in today, and Salesforce.com did right by itself and its customers with its platform announcements at Dreamforce.

I wish I could be as bullish on the social/trust message that was the gist of CEO Marc Benioff’s keynote and comments to the press and analyst corps. I remain a social skeptic, particularly in terms of how well the social/collaboration theory works in practice inside the enterprise. It’s irrefutable that this social/collaboration stuff works brilliantly in the B2C world (if by brilliantly you accept the fact that the industry is using social to define the latest way to turn loyalty into upsell opportunities, something as old as S&H Green Stamps). But in the internal operations of the enterprise, the adoption of social technology is still of limited value.

The problem isn’t the technology, it’s the fact that social software is not innately engaging or proscriptive – it neither compels employees sufficiently nor tells them what to do in order to be more social or collaborative. Hence the irony of offerings from the likes of gamification vendors like Badgeville, which announced a gamification offering to help shore up the engagement of Salesforce.com users in their social/collaborative activities. We still have a long way to go to bring the success of B2C social collaboration into the core of the enterprise, and the numbers show it.

But that’s okay, Benioff is getting tons of cred as a visionary for pushing this vision (cf the posts from many of my fellow Enterprise Irregulars), and meanwhile that visioneering is driving tens of thousands of customers and hundreds of partners to Dreamforce and the growing Salesforce.com ecosystem. And while at the end of the day the business at hand is still good old CRM and a few adjacencies,  that’s okay too. Because it’s clear the there’s some serious bets being made by Benioff and company on the future of the enterprise, and the foundational elements are starting to emerge. And with it the continued leadership of the market pioneer, new refrigeration appliances notwithstanding.

It’s a sad day when the bar is set so low that a company’s most successful endeavor in recent memory involves a new slogan and ad campaign tied to the Olympics, and the best news to date is that it won a lawsuit it should never have had to engage in. Such is the state of Hewlett-Packard today, a once mighty force in technology that’s now relegated to a status that can best be described as dire.

News from the last quarter only compounds how dire things have become: a $1.5 billion charge against earnings due to a greater number of employees taking an early retirement package than had been anticipated.  As if HP could afford to lose talent. To paraphrase the old aphorism: Those whom the gods wish to destroy, they first deplete of their valuable employees.

The brain drain on top of the increasing irrelevance of HP in many key markets and its inability thus far to credibly enter any new markets makes the question that remains not whether CEO Meg Whitman can keep HP alive, but how she will dismantle HP into something that is both manageable and relevant in today’s market.

If even that option remains.

It’s been almost a year since that fatal day in August 2011 when then-CEO Léo Apotheker, following the misdirection of a board that was asleep at the switch in so many well-documented ways, announced the possible spinoff of HP’s PC unit, the death of Palm, and the acquisition of Autonomy. The ensuing firestorm undeservedly cost Apotheker, his head of communications, HP’s long-time CTO, and numerous others their jobs and their reputations.  It was as shocking a misfire as I have ever seen in almost 30 years of covering the IT industry.

Into the breach road Meg Whitman, promising stability and leadership and armed, one would assume, with an ironclad agreement that she would get more than the paltry 11 months Apotheker was given to clean up a mess that was decades in the making.

With the close of Whitman’s first year rapidly approaching, I think it’s safe to say that not much has changed for HP.  The company’s revenues and market share continue to decline as core markets like PCs and services fall apart. The Autonomy acquisition, which couldn’t have been undone even if Whitman had wanted to, has proven to be as troubled as most of the company’s other large acquisitions – witness the untimely departure of Autonomy CEO Mike Lynch in May, six months following the acquisition, and the complete absence of a public strategy to integrate Autonomy and create a pan-HP value proposition around its enterprise search capabilities.

Meanwhile Palm is dead (though it appears that HP is trying to keep a zombified version of Palm OS alive), HP lost Vyomesh “VJ” Joshi, the driving force behind its highly successful printer division, and partnerships with the likes of SAP have been troubled by the inability of HP to move fast enough on the hardware side to keep pace with its partners’ software innovations. Meanwhile, EDS is being gutted amid a planned $8 billion write-down, having proven in one quarter too many that it has been unable to adapt its go-to-market to pick up the large volume of smaller, strategic deals that it needs to turn in consistent quarterly success.

There is some good news: HP Software – which in retrospect may be happy it was kept separate from Autonomy – is building out a strong cloud management capability, and the systems business has some impressive products and may be getting an infusion of good karma from the HP/Oracle lawsuit ruling. The printing division has more than a few cool products and innovations up its sleeve, and HP’s latest ad campaign had someone holding what looked like a new HP Slate tablet, hopefully targeting the pending Windows 8 launch.

But the problem that bedeviled Apotheker, and would have still weighed on him even if he had not been fired last year, still remains: there is no pan-HP strategy, no way of talking to the market about how the whole is greater than the sum of the parts, no synergistic product set that taps into the company’s ability to provide a mix of services, hardware, and software that, taken together, provide that value-added positioning that would remake HP’s tarnished brand.

Instead, HP remains the company that Apotheker’s predecessor, Mark Hurd, was able to run to the short-term satisfaction of investors and to the detriment of anyone – employees, partners, customers – interested in long-term value: A company that in reality is a federation of completely separate entities, rarely working in unison, hopefully not too often at loggerheads, unable to cross-sell, and stuck in the corporate version of the Peter Principle, having risen to its level of incompetence and unable to go any further.

Not that HP isn’t trying, at least on the branding side. Its new “Make It Matter” spot, shown during the Olympics, is the culmination of a year-long effort that is as much targeted at the outside world of customers and partners as it is at the employees who, for good and bad, are apparently running for the exits in unexpected numbers.  In that spot, the message is clear – the power of technology to help people  work, achieve their dreams, learn, create, and change the world is HP’s birthright, and that’s what matters. Mixed into the visuals are the many ways in which HP already makes those aspirations come true, and it shows a cool side of HP that most people have no idea exists. In short, it’s a well-done piece worthy of the aspirations of a once-great company.

But the question remains: it is already too late to make those aspirations a reality? Can HP really matter to the market again?

My sense today is that it may be too late, at least for the federated HP that aspires to be like IBM in 2012 but looks more like IBM in 1993 – on the ropes and losing relevance and market share. In order for HP to be what it aspires to be would require not just a great pan-HP strategy but the rapid and flawless execution of that strategy, and that’s where I get a little pessimistic. It’s hard to turn around a company whose employee base is so massively demoralized, where the silo mentality is so engrained that acquired employees continue to use email addresses ending in eds.com and palm.com years after their companies were acquired, and where the third CEO in three years has yet to do more than triage a company that is seriously in danger of succumbing to its wounds.

What Whitman needs to do, in my opinion, is emulate Steve Ballmer: sign on to a strategic vision – the cloud, in Microsoft’s case – and then move everyone in the company, many kicking and screaming, towards this vision. Put a little slogan in the mix and make everyone in the company use it as a tag line – we’re all in became the de rigeur sign-off for Microsoft email messages  – and repeat it until it actually starts to sink in. And then tell Wall Street and the likes of Vanity Fair to stuff it, ride out the criticism, and start moving product strategy forward.

And, while there are those that think that Ballmer has laid an egg with his new approach (and I’m emphatically not one of them), even his detractors will have to admit that Microsoft as a company has a vision and is engaged in it, the employees are excited, and there are some seriously interesting gambles on the table – Azure, Windows 8, Kinect, to name a few – that could, and will, IMO, turn Microsoft around.

Going the Microsoft route is hardly a guarantee for success, in part because it takes years (Microsoft has been at its new vision for at least five years, and probably needs one more year to really make it solid), and in part because coming up with a truly momentous vision is harder than just about anything else in the technology industry. And even harder still when triage continues to be job number one two years after Hurd left.

In the end, vision will be the test of Whitman’s tenure, if she makes it past the one year mark. And my sense is that her vision will not include every one of the business units that make up HP today, mostly because it’s hard to envision how to bring together a dying PC industry, an increasingly commoditized printer and server business, a chronically underperforming services business, and a Software division that doesn’t actually own most of the company’s software assets, and forge a great, new strategy that the entire company can march towards. It’s clear HP is trying with its cloud strategy, and there may still be something to do with business analytics that is meaningful, but these are initiatives that would have been visionary if they had started under Hurd’s tenure. Today they look too much like me-too, catch-up strategies instead.

Fixing all of HP is just too hard. Even if the CEO was named Meg Wonder Woman, I wouldn’t bet on her being able to bring so many struggling lines of business together and make them matter. Something will have to go away in order for HP to live on, and I would expect that a year from now HP will have been significantly downsized if it is, indeed, going to continue to matter at all. Some things are just too big for their own good, and HP today may be just one of those things.

Dell Software last week held what it promised was the first of many media days intended to describe to analysts and the press how the erstwhile PC and server vendor plans to become a software powerhouse.  Breaking the historical mold is a common theme these days, with software companies like Oracle and Microsoft  looking for redemption in the hardware market, enterprise apps vendors like SAP moving into the database market, companies like Dell and HP trying their hand at enterprise software, and Yahoo trying to move beyond search.

While the what – what new products, what new services, what new markets  – is important in these gender-bending strategic shifts, the real issue on the table is always how: how can such a massive cultural change be undertaken without destroying the core business? How can new sales methods and channels be nurtured and maintained, new markets defined and conquered? And most importantly, how can these new aspirations, which are invariably about attacking an established market already replete with existing and not always thriving vendors, come with enough unique value-add to rise above the noise?

This is the essence of Dell’s aspirational foray into the enterprise software market. The what is clear –  a set of midmarket products and services focused around cloud integration (Boomi), systems management and security (Quest,  Sonicwall, among others), and business intelligence (insert unannounced acquisition or internally developed product here) to start, with more unspecified but hopefully value-added enterprise applications to come.  But the how remains to be seen, and whether Dell  succeeds in enterprise software will depend on a broad set of how to capabilities that the company has only just begun to build out.

Number one on the how to list is how to sell high-value software and applications services from a company not well known for these capabilities. While Dell Software CEO John Swainson bravely offered up 20,000 existing direct sales people as the vanguard of this effort, the truth is Dell will need much more than desktop and server sales people to up the software ante with the customer.

To Swainson’s credit, this field sales force has the relationships needed with the SMB market to get the ball rolling, and that’s saying a lot. But someone else will have to show up in the buyer’s office to make a pitch about  Dell’s business analytics and other software offerings, especially as Microsoft and the rest of the competition will have their relatively able channel partners outside waiting for their chance to bat.

Where that software sales force will come from remains unclear – Swainson wants 70% of his business to come from direct sales, and that’s going to mean hiring and training a boatload of new people. And those people need to live and work in some very interesting places: Swainson also wants to tackle emerging markets – the BRIC (Brazil, Russia, India, China) gang, among others – which means competing with already established local companies and the many many global software companies now carpet bagging in the BRIC market for quality talent. Not easy.

How to number two comes in the form of the need for verticalized, high-value solutions, particularly in the oversaturated BI market. While it’s hard to build great horizontal BI apps, building high-value vertical apps is bloody difficult. But horizontal BI is very 20^th century in terms of strategic value, and Dell will have to go for the bloody difficult option and still face an uphill battle overcoming a broad base of established – and, in many cases, enormous – BI vendors as well as a constant churn of venture funded BI companies all heading for the so-called low-hanging fruit of big data BI.

While Dell wants to start slowly, with more of a horizontal play that provides end-user tools (a la Qliktech) to do cloud-based analysis (a la Gooddata), they’re going to have to up the ante pretty quickly or hope that the Dell brand carries more value in the BI market than I think it does. Right now Dell has a data warehouse appliance and some vertical solutions built by the company’s consulting services, but they’re going to have to do a lot more to get moving in BI. A lot more.

Cloud-based integration and data management are the apps spaces that Dell is already a mature player  in (security and systems management are also quite mature, but they’re not really enterprise apps per se.) This is thanks to the Boomi acquisition, and from my conversation with Rick Nucci of Dell Boomi it’s clear that the enterprise software integration market isn’t an aspiration here, it’s real. But Boomi faces the same challenge of how to move upstream with its cloud integration play, though it has a fair amount of runway for now helping integrate the nascent cloud-apps market. And while there are limits to how upstream integration can go, Boomi is wisely targeting master data management and more high-value business process integration services for its next integration value-add play.

The third how to is how will Dell consolidate its consulting services around enterprise software. Right now the different software assets, like newbie Quest or Boomi, tend to deploy their own consultants rather than rely on Dell Consulting, which, with its Perot Systems roots in infrastructure implementation and outsourcing, isn’t considered a go-to systems integrator for enterprise software. That’s okay in the short term but short-sighted in the long term. Just ask HP: EDS has had massive problems with the exact same transformation, and so far all Meg Whitman seems to have been able to do about it is layoff EDS staff. If Dell can’t refocus its old Perot Systems consultants on new enterprise software opportunities, both Perot/Dell and Dell Software will suffer.

The final how is really the meta question looming over all of  Dell’s software aspirations: How can Dell differentiate itself in software in some unique and highly remunerative way? As Swainson hypothetically posited growing Dell Software from its current $1.5 billion in annual sales (including Quest) to $5 billion  in revenues at 30% margins, we’re talking some serious growth aspirations.  How? Swainson and team pointed to several ways to meet this lofty goal, including focusing on the SMB market, focusing on the BRIC countries, focusing on great technology, focusing on leveraging hardware and software assets, and leveraging the Dell brand.

Is not a bad list, but I’m not sure it’s enough.  Among other factors, the massive head start that companies like Microsoft, SAP, and Infor have in enterprise software, the mid-market, and the BRIC countries will make Dell’s software dreams harder to realize than it may seem. And while the focus on BI sounds great, considering the massive growth of big data, blah, blah, blah, I didn’t hear anything new that showed serious out-of-the-box thinking. Maybe Dell Software has something up its sleeve, but it wasn’t on the agenda for the day.

The reason for the blah blah blah above is that big data and BI/analytics are unfortunately one of the default modes for vendors looking for that new new thing. Vendors tend to fall back on BI and analytics for new strategies the way Hollywood drops a vampire or werewolf into a teen movie plot in order to draw a crowd.  BI/analytics and big data are that same deus ex machina plot twist: it’s easy to see how poorly the market is served by the tools vendors, easy to see how complex the problems of big data have become, easy to see how some established vendor flying the flag of neutrality could emerge with a big chunk of that homeless, tempest-tossed, desperate-for-real-business-intelligence market.

Easy to see, hard to execute. Really hard.

So in the end we’re left to take on faith some basic concepts regarding Dell Software. The first is the leadership team – they’re solid, and experienced, so there’s a decent chance they’ll get it right. The second is the opportunity – no argument there, the mid-market needs help with data, systems management, and BI. And the third is the Dell brand does count for a lot, and its saturation in the mid-market is impressive. So, as long as this is the first of many outings for Dell Software, and the company remains committed to staying the course despite the early obstacles, and it figures out the critical how-to factors, there’s a solid chance that the shift from hardware to software will work for Dell.

Considering the declining fortunes of the PC business, it’s a chance Dell has to take. In the meantime, we’ll have to wait and see how much more substance Dell Software can add to the picture. There’s a lot more to prove here than just good intentions and a good management team. A lot more.