When I left Microsoft at the end of 2011, they had just launched the developer version of Windows 8 at the BUILD conference after building anticipation for months using flashy teases and deep secrecy. And the secrecy was real; I remember getting daily reminders of the civil, criminal and economic penalties for leaking even the smallest detail of what we were building. There were even rumors of some unlucky employee who got fired for stepping a little over the line, his head on a pike to serve as a warning to others (metaphorically speaking, of course). The goal here seemed clear: take a page from the Steve Jobs consumer playbook, saving all of the thrills for the stage.

This was quite a departure from the behavior eight years earlier when I’d first joined Microsoft and the halls were decorated with signs saying “Enterprise! Enterprise! Enterprise!” to remind us who our most important customers were. At that point, Microsoft owned the consumer desktop with Windows and Office everywhere, so to continue to expand its revenues, it needed to take over as big-iron Unix boxes were losing favor.

At the time, the main competitor was a grassroots upstart: Linux and open-source software. Because of the focus and the clear competitor, Windows Server turned into a monster at the box office, winning both critical acclaim and audience approval. In the process of turning itself from a consumer company to an enterprise company, Microsoft learned how to be open, solid and trustworthy—all things that enterprises need when choosing technologies they’re betting their businesses on.

When Microsoft left the consumer PC space behind, it took comfort in the fact that it owned more than 90% of the desktop market share. And it still does. The problem is, while Microsoft was away chasing the enterprise, Apple changed the game. Now it’s about phones and tablets, where Microsoft has tried and failed to make traction for years.

The way Microsoft is currently trying to do it is by imitating Apple with secrecy, flash and thrills, all of the things that it has spent the last decade weaning out of its culture; enterprises hate those qualities. Unfortunately, while Microsoft is trying to be the next Apple to regain the traction it lost in the consumer space, Apple is busy increasing its foothold into the enterprise.

When Microsoft was fighting Linux in the server space, Linux was making inroads because it was free, capable, and IT administrators liked using it. It started in small and medium-sized businesses because of the cost savings, and grew to the Fortune 500 because of its capabilities and community support. The grassroots snuck Linux into the back room, and it stayed there. In fact, one of the ways that Windows Server became so successful was by embracing the heterogeneous nature of many enterprise environments.

About Chris Sells