Redmond exec says businesses must face up to the cultural challenge of moving to a services-led world.
Migrating from Windows XP is crucial but "bloody hard to manage and expensive to deal with" said a Microsoft executive.
Chief Envisioning Officer Dave Coplin told CBR that businesses stuck on the out-of-support operating system must upgrade, as statistics show that XP still accounted for 25% of all desktop web traffic in May.
He said: "Thinking of it in terms of competitive advantage, XP ‘s what, 13 years old, and when you realise how crucial technology is to the way you run your business, you’re saying you really want something that’s that old? It just doesn’t make sense.
"The flip side of that is it’s bloody hard to manage and expensive to deal with and it causes a whole load of grief with your employees when you change it."
Microsoft stopped providing patches for bugs affecting XP in April, meaning users who remain on it risk being hit with malware.
However, data from Net Applications demonstrated that one in four desktop internet users still relied on the operating system last month, just 1.2% less than in April. Microsoft declined to disclose where in the world these users reside.
Coplin said it was important for businesses to keep up to date with technology, whether it be operating systems or other IT innovations, but warned that a culture change is often required to do so.
He said: "I worry a lot about this. I want the technology experience to be the same at work as it is at home, but we treat those quite differently at the moment.
"We need a much more fluid approach. If the culture of the company isn’t in the right place then technology isn’t going to solve it. Technology is very important but you have to get the culture right first for the technology to be really effective.
"The way we’re going, and Office 365 is a good example, when we move to a world of services rather than things you roll out every three to five years, the world fundamentally changes."
Meanwhile Microsoft said it continues to work closely with customers and partners to help them transition from XP.
The antique OS accounted for the second-highest share of desktop web users in May, according to Net Applications, with only Windows 7 having a higher stake, at 50%.
While CBR couldn’t find any reliable count for the number of remaining XP users, a survey of 5,000 companies by security firm Bitdefender concluded in May that one in five SMBs still ran the operating system.
Windows 8 contributed to 6.29% of desktop web traffic last month and Windows 8.1 contributed to 6.35% of traffic (up from 5.88% in May), but Redmond said it is confident that 8.1 will take off.
A spokesman said: "We are very confident that customers see the value of upgrading. Windows 8.1 is the operating system for modern business. It builds on Windows 7 fundamentals like increased speed, reliability and security, while creating a modern platform designed for a new generation of hardware experiences – from tablets and innovative touch devices to traditional desktops and laptops.
"Windows 8.1 is great for businesses because it is designed to deliver the experiences people will want and provide businesses with the enterprise-grade capabilities they need."
It added that users still running XP risk losing personal and business data to viruses, spyware and other malicious software.