How the Stylus Doomed Microsoft's Phone Business

In a wide-ranging interview, Steve Ballmer this week was asked to explain what went wrong with Microsoft’s smartphone business. He pointed to skepticism over iPhone carrier subsidies, but I have another idea.

As someone who was burned by the iPhone, I know why Microsoft screwed up. Since I was unable to secure any hands-on time with the iPhone prior to its release, I based the criticial columns I wrote about the device (April 2007: The iPhone Can’t Live Up to Its Hype) on the fiasco I saw with Microsoft phones.

Once I got my hands on an iPhone, my tune changed fast; I had to admit the device was a world changer. Not so for Microsoft; Ballmer had nothing good to say. It was peculiar. What was Ballmer not seeing?

I am now convinced it had to do with Ballmer’s personality and nothing more. Steve Ballmer, I will argue, is a neat freak. He is organized. Button down. He may yell and scream and seem slovenly, but really, he’s just boisterous.

He probably had a Palm Pilot with a stylus, which were all the rage back in the day. When you visited many random Silicon Valley corporate headquarters, the reception desk would have a bowl of free styli for you to take, compliments of the house. “Take a few” was a common refrain; I still find them randomly around my house.

Unlike the rest of us, Ballmer is probably the type of guy who never lost his stylus and scoffed at the notion of a touch-screen iPhone. Thus, he could not really understand its genius.

Just look at how long it took to get the first true Windows phone to market. The company could have easily re-jiggered the old software by enlarging the icons and getting rid of the stylus, but no. There were obviously philosophical debates going on about the stylus and other features. Microsoft had already partnered with Sony and Ericsson and could have followed the path that Google took with Android to quickly release a mobile OS. It already had software.

Instead, it partnered with Nokia, which was conflicted with its miserable Symbian software and the rest is history; one ill-conceived botch after another.

Nobody normal felt any love for the stylus. It was practical, but annoying. Now, put yourself in the mind-set that the stylus was great and necessary. Imagine (if at all possible) that you could never lose it and it was anything BUT annoying. This had to be the mindset that kept Microsoft from transitioning to the modern smartphone with any alacrity. It made no sense to them.