Update and upgrade roadmap crucial to Windows 9 success

Analysts today will be closely monitoring Microsoft's Windows event to hear how, or even whether, the firm can reconcile its fast-paced release cycle with the more conservative needs of enterprises.

"They need to explain how they can have their cake and eat it too," said Patrick Moorhead, principal analyst with Moor Insights and Strategy, of Microsoft. "Longevity and [upgrade] cycle are huge to the enterprise, but if Microsoft elongates [the release schedule] it risks losing competitiveness on the consumer side. The company has to somehow keep up with consumers, who want features now, but also cater to the desires of enterprises, which want a more planned and conservative upgrade path."

Later today, Microsoft will hold a one-hour press conference in San Francisco where it will reveal some aspects of the successor to Windows 8, which corporations have largely rejected. All that's certain about the event is that Microsoft will target its message at those thanks-but-no-thanks customers.

The press conference, slated to kick off at 10 a.m. PT (1 p.m. ET) will not be webcast live.

Analysts interviewed by Computerworld on Monday were unanimous in their hopes to hear or read more information about how Microsoft will distribute Windows 9, as some have preemptively and presumptively called it, and how fast it and its inevitable follow-ons will be offered or forced on corporate customers.

The topic is not new.

Industry analysts have questioned the faster cadence, which Microsoft kicked off last year with Windows 8.1, then accelerated with Windows 8.1 Update in April 2014, particularly when Microsoft demanded that customers running the former move to the latter within months or lose patching privileges.

The tempo ran counter to both Microsoft's traditional process and the migration and patching practices of large companies, especially those that must comply with strict regulations, such as the financial sector.

Customers pushed back against the pace earlier this year. Initially, Microsoft gave everyone just one month to migrate from Windows 8.1 to Windows 8.1 Update, but quickly recanted, giving commercial customers four months to install the latter.

That's what makes an update and upgrade roadmap from Microsoft so newsworthy.

"This is pretty important," said Michael Silver of Gartner, referring to clarification of how Microsoft intends to deliver Windows 9, its updates and its successors. "Without it, this is going to be Windows 8 all over again. Windows 9 will be a non-starter, because if enterprises don't know [more about the cadence] why should they even listen to anything about Windows 9?"

Wes Miller, an analyst with Directions on Microsoft, a research firm that specializes in tracking Microsoft's moves, agreed. "What is just as important [as the content of Windows 9] is whether Microsoft continues the faster cadence," said Miller in a Monday interview. "They're going to have to be careful how they message it."

Miller was cautiously optimistic that Microsoft would come through. "I sure hope they do" talk about the update roadmap, he said. "Businesses who plan for the long term need a longer term that they can plan to."

The problem, and it's also not new, is that Microsoft wants to be all things to all customers. But its two broad customer categories, consumer and commercial, are so different that to shoehorn Windows' update practices into both leaves neither satisfied.

Some analysts have urged a solution on Microsoft that would separate updates and upgrades for consumers from those destined for the enterprise, creating a dual-track process where consumers get new features and user interface (UI) changes faster while companies can opt for a slower tempo.

Without a clear roadmap, experts claim, Microsoft's biggest customers will simply sit out any OS refresh, and stick with the more traditional Windows 7, which has become the enterprise standard.

That, in turn, could resurrect the Windows XP problem in five years, when Windows 7 exits support. Businesses stayed with the 2001 operating system far too long -- at least in Microsoft's opinion -- and then had to hustle to replace it with something newer when patches dried up in April. The same seems likely with Windows 7.

"Microsoft has to come to terms that [commercial] organizations and consumers are different," said Silver.

While today's news conference will not be broadcast, Microsoft has said it will post several background pieces to its website shortly after the event's conclusion, including to its Blogging Windows blog.