Cloud-based integration and data management are the areas in which Dell is already a mature player. (Security and systems management are also quite mature, but they're not really enterprise apps per se.) This maturity is thanks to the Boomi acquisition, and from my conversation with Dell Boomi's Rick Nucci, 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 question is how will Dell consolidate its consulting services around enterprise software? Dell's different software assets, like newbie Quest and 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 run. Just ask HP: EDS has had massive problems with the exact same transformation, and so far all Meg Whitman has been able to do 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 a unique and highly remunerative way? Swainson hypothetically posited growing Dell Software from its current $1.5 billion in annual sales (including Quest) to $5 billion in revenue 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, the BRIC countries, great technology, as well as leveraging hardware and software assets, and the Dell brand.

It's 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 midmarket, 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 the other day.

The reason for the blah blah blah above is that big data and BI and analytics are unfortunately one of the default modes of vendors looking for that new new thing. They 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 machine 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-BI 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: It's solid, and experienced, so there's a decent chance it'll get it right. The second is the opportunity: No argument there, the midmarket needs help with data, systems management, and BI. And the third is that the Dell brand counts for a lot, and its saturation in the midmarket is impressive.

So, as long as this is the first of many outings for Dell Software, the company remains committed to staying the course despite early obstacles, and it figures out the critical how-to factors, there's a solid chance that Dell will make the shift from hardware to software work.

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.