Businessweek’s “Caption This” for Ballmer: “No More Mr. Monkey Boy”

His face looks like the 3D movie version of some happy-go-lucky cartoon character, so for some, concocting a Charles Addams-like killer caption for Microsoft CEO Steve Ballmer is irresistible. On Friday the 13th, of all days, the Bloomberg Businessweek cover (for those of you who still read magazines) will feature Ballmer’s face along with its own idea of a “Caption This” contest entry, literally plastered in pink all over him.

Perhaps unintentionally, the presentation comes off like a political statement, maybe as phrased by a Microsoft shareholder.

The caption, “No More Mr. Monkey Boy,” refers to tomorrow’s cover story, “Steve Ballmer Reboots” by Ashlee Vance. The story appears on now, and appears to be part of Microsoft’s attempt to reset its CEO’s image to that of an easy-going, smart, sensible fellow – one you’d like to share lunch with sometime, and not by means of a slot beneath the cage door. All the points that Microsoft’s marketing would have wanted to touch upon are touched upon, as though recited from a PowerPoint presentation, including the company’s effort to make up ground in the cloud.

In his story, Vance recaps Microsoft’s cloud strategy mostly from a consumer perspective, making sure to include Zune, Xbox, SkyDrive, and even the recent Skype acquisition in the mix, although the latter may be somewhat of a stretch. “The fullest expression of Ballmer’s ambition is Microsoft’s cloud computing strategy,” Vance writes. That statement soon appears to be contradicted by a quote from startup analytics firm Kaggle, whose chief scientist says, “When you talk to other entrepreneurs and tell them you’re using Microsoft’s cloud services, they look at you like you have leprosy.”

It’s the negative image, and specifically the one attributed to Ballmer himself, that Microsoft is working to escape. If the Businessweek story counts as its latest move in that direction, then that’s at least three that could be considered as having backfired. Last November’s company shareholders meeting, according to all reports, was less than one hour in length, and cut short the Q&A session while grumbling shareholders waited at the microphone. Then the Monday keynote at CES 2012, said to be Ballmer’s and Microsoft’s last, was roundly excoriated by critics who expected the CEO to present a bolder, clearer strategy, as opposed to a list of underdeveloped brand names.

Truth of the matter is, compared to the fellow we saw on stage Monday, Microsoft and its customers could use a bit of the old “Monkey Boy” right about now.

CORRECTION: Mr. Ashlee Vance has corrected this reporter as to his proper gender. My sincere apologies for the error, and yes, I officially am a monkey boy today.

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