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.”