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The Microsoft challenge Steve Ballmer leaves behind

The Microsoft challenge Steve Ballmer leaves behind

I’ll never forget the sheer physical presence of Steve Ballmer the first time we met. It was a little intimidating to shake the hand of the man who had only recently become Microsoft’s second-ever CEO, and he had a very firm grip. He seemed like the kind of guy who could easily bust a door or break some Windows. Instead, he may be remembered as the guy who broke Windows.

When Bill Gates left Microsoft in the early 2000s, the company was still the dominant force in the technology sector, a company that was slow to embrace the Internet and mobile computing but whose desktop domination seemed invincible.

Ballmer’s tenure proved it wasn’t. That Apple -- a company that once had to go cap in hand to get a cash injection of $150 million from Microsoft in 1997, would one day surpass its longtime rival in market value was once unthinkable. Now it just seems inevitable. Like BlackBerry, which began as an organization aimed at corporate users that can’t seem to find its ground among consumers, Microsoft has lost traction. It is far more diversified than BlackBerry, of course, and the company will continue to own a sizable chunk of the market long after Ballmer retires within the next 12 months. It’s just that unlike when Gates stepped down, Ballmer’s departure suggests Microsoft needs to undergo a significant transformation in its leadership, its culture and its product line.

“There is never a perfect time for this type of transition, but now is the right time,” his memo said. I’m not so sure. A big part of running a company’s of Microsoft’s stature is having a good succession plan in place. Instead, Microsoft is performing a special committee to begin the search process. It creates an unnecessary cloud of uncertainty around Microsoft’s short-term future while simultaneously leaving no doubt that everyone involved agrees a fresh start -- a departure from Ballmer’s vision -- may be critical.

Ballmer never had the charisma of Steve Jobs and there will be no movies based on his life like the Apple founder’s biopic coming out this month, but he’s not without his charms. Go on YouTube and look up his appearances at Microsoft developer conferences, where the self-styled “Monkeyboy” dances around the stage with a manic energy that was, in its own way, infectious. And unlike Jobs or even Gates, who often came across more defensive about their choices than anything else, I was surprised at how often Ballmer would acknowledge mistakes or lessons learned, whether it was the first time I met him following the challenging launch of Windows Vista, or the second time not long before the launch of Windows 7. He also seemed entirely sincere in a humble ambition to do better.

Unfortunately Ballmer’s most significant moves, like the recent reorganization dubbed Microsoft “One,” are behind-the-scenes affairs that don’t contribute to a compelling legacy. Instead, his time at the helm was marked by dud products like the Zune music player, the so-so Surface tablet and the back-to-the-Start mishaps of Windows 8.

Much will be written and discussed in the next few months about what Ballmer did wrong, but we should also remember that he was cast in the same, unenviable position as Apple’s Tim Cook in taking over from a founder amid colossally high, perhaps unrealistic, expectations. At its height, Microsoft’s slogan was, “What do you want to do today?” Ballmer’s struggles show just how important technology vendors focus instead on figuring out what we’ll want to do tomorrow.