And for all the blogs that Sinofsky wrote -- something he apparently took pride in, mentioning them in his final memo to his team -- under his leadership, there were simply too many glaring gaps.
"With Vista they were too sharing, but with Windows 8, they went too far the other way," said Cherry. "And they paid the price. The lack of useful apps for the Surface at launch, the lack of information to developers, definitely damaged the effort. Microsoft didn't oversell the features, that's certain, but now they're paying the price. Enterprise deployment and app development is slowed because of a lack of information.
"The lack of sharing with OEMs and app developers is the reason why there are so few good apps in the [Windows] Store," Cherry said.
He used an example to hammer home the point. "If you're an enterprise, does the Microsoft account interact at all with Active Directory, or are they two separate worlds?" he asked. "Microsoft seemed to be unwilling to share that information."
Miller concurred, and used his seven years at Microsoft, which he spent in the Windows Core and MSN divisions, to illustrate.
"When I worked on the rapid adoption program for Windows XP and then later, for Office XP, one of the key things was sharing information on what we were planning with OEMs and customers," said Miller, referring to a program Microsoft uses to get feedback from customers, usually large organizations, on features during product development.
"There was always a steady flow of information," Miller said. "But I know a very large petroleum company that has had so much frustration over the last year, about what's coming, how it will be licensed. It's not just analysts and the press who are unhappy with the secrecy. It's everybody."
Other analysts, some of whom have long talked about the change in information dissemination since Sinofsky took the Windows reins, chimed in, too.
"Sinofsky was said to alienate ISVs, [independent hardware vendors], retail partners and customers with his Microsoft-first attitude," said Patrick Moorhead, principal analyst with Moor Insights & Strategy, earlier this week.
Now that Sinofsky is out, Microsoft as a company, or Larson-Green and Reller, as Windows' new leadership, have an opportunity to correct that course.
"Maybe what we might see from the new regime is a more open communication channel with the [Windows] ecosystem," said Cherry.
Miller agreed, saying that Microsoft should try to regain the trust of its OEMs, outside developers and customers. "They have a lot of opportunity in front of them in the next six months, not only to not abandon Windows enterprise users, but to begin evangelizing Windows 8, and even Windows 7," he said.
Sign up for CIO Asia eNewsletters.