Windows 10 upgrade cycle has CIOs bracing for (and embracing) change

CIOs say the shorter upgrade cycles for the Microsoft Windows 10 operating system are a breath of fresh air. Microsoft’s previous approach of protracted revisions seem antiquated in an era of constantly refreshed cloud and mobile platforms. Windows customers say that while the shift is another sign that the 40-year-old software giant is modernizing its IT delivery processes, managing the change will take significant effort.

"Historically, your Windows upgrades were these massive projects -- going from Windows 95 to XP and XP to Windows 7," says Alaskan Airlines CIO Veresh Sita, who has purchased several Microsoft enterprise products during his 20-year career as a technology manager. "What we're moving to is more of an evolutionary, organic mode where I don't need to upgrade the whole company to a new stack. The deployment method, the way it gets scheduled and the way you go through the upgrade process is no longer a burdensome process."

[ Related: Windows 10, the stealth OS ]

Delivering Windows 10 as a service -- the way most upgrades to cloud and mobile applications are delivered today -- means lighter-weight feature functionality, user interface changes and security upgrades every few months rather than a Big Bang revision every few years. CIOs can provision upgrades with the click of a button, not unlike how you accept an upgrade for Starbuck app on your iPhone. This service-based method will replace forklift upgrades conducted by teams of engineers certified to work with Windows.

Over-the-air upgrades fly with this airline

Sita says the airline is testing certain applications to run on Windows 10, noting that the upgrade from Windows 7 to Windows 10 will be fairly seamless. However, his team will have to rewrite some flight operations applications developed for Windows 7 to make them compatible with Windows 10. While he says it’s going to take some effort, ultimately Windows 10's interoperability with Microsoft's Office 365 productivity suite as well as Microsoft Azure cloud services, which Alaska Airlines is upgrading to, will save the company significant amounts of software "retro-fitting," a process his teams have traditionally conducted to ensure compatibility. "The issues of one product not working with another will diminish because it's part of a blended ecosystem," Sita says. "Those upgrades will happen organically all of the time."

Incremental changes, such as new search functionality and other features, can ease employees’ transitions to the new software, saving CIOs the time and staff resources required to train up employees on major upgrades, says Orvis CIO Dave Finnegan. He says that while Orvis is not officially testing Windows 10, Microsoft has demonstrated the software for him at a testing lab in New York City, and his engineers are informally testing it. “There’s no fighting that this is the better model – it’s a done deal,” Finnegan says. “It’s really a question of how we incorporate it.”

[ Related: Windows 10: Adapt or die ]

Organic, over-the-air upgrades provided by a raft of cloud and mobile vendors, from Amazon Web Services to Apple, are part of the change management challenge that define the new style of IT. CIOs need to ensure that they support the devices and applications employees choose to use for work, and that those technologies are compliant with corporate policies, says Clay Johnson, CIO of GE Power and Water. He says employees who are told they can’t upgrade to the latest version of iOS or some other software will work around it or become disgruntled and leave, he says. Johnson recently began testing Windows 10 on his corporate laptop; the company is on track to roll out Windows 10 in the first quarter of 2016.

Splunk employees who wanted new features from previous Windows versions would have had to wait months for upgrades, says the company’s CIO Declan Morris. "The fact that they are parsing it our as services is a good thing," he adds. However, he cautioned that CIOs need quality-assurance processes in their desktop engineering group to ensure that corporate applications are compatible with each quarterly upgrade.

Morris says the company is currently testing Windows 10 and plans to make it available to PC users, which comprise 45 percent of the company's 1,800 employees, when the software is more polished. "If you take your eye off the ball, it's going to come back to haunt you," he says. "You're going to get crushed on the back-end as people submit help tickets."

Why Windows 10 has one CIO a little nervous

One thing that may not sit well with CIOs is that, with some exceptions, they will need to adopt updates in order to receive security fixes. This is a break from the traditional approach of Windows upgrades, where CIOs could upgrade software on their own cadence.

That has some first-time CIOs, such as Connex' Credit Union's Dennis Klemenz, leery of Windows 10's upgrade velocity. While working as a manager of business intelligence systems at Sikorsky Aircraft, Klemenz recalls Windows upgrades as a "controlled" upgrade process, requiring extensive interoperability testing for each new service pack. While he says he understands Windows 10’s iterative upgrade process allows for quick feature and security provisions, he's concerned it could break some of his enterprise computer systems. “I have systems that are reliant on Windows as my operating system, so it makes me a little nervous,” Klemenz says. "There’s no guarantee that there’s not going to be issues.”

[ Related: Gartner guru 'shocked' by corporate reaction to Windows 10 ]

Gartner analyst Stephen Kleynhans told Computerworld that CIOs will have to institute a kind of "production-line model," to manage the change Windows 10. This entails creating tasks that are repeatable and in constant use, requiring additional development diligence. As one update's deployment starts, the next update's preliminary testing should already be in motion, he says.

Change management challenges aside, CIOs are moving quickly to Windows 10. Roughly 60 percent of IT departments have either tested or are currently testing the new operating system, according to a June Spiceworks survey of 500 IT professionals. The survey also found that 40 percent of companies plan to begin rolling out Windows 10 within the first year, with an additional 33 percent expecting to begin deploying Windows 10 within two years.