Watch Microsoft Hire an Enabler as CEO

NEW YORK (TheStreet) -- Comments made on Friday's Microsoft's Pointless Search for a Loser CEO illustrate the organizational hurdles the company -- and, evidently, some of its supporters -- refuse to jump to reshape the increasingly irrelevant giant.

For example ...

This article should be deleted, it contributes nothing to the stock discussion.

The reaction underscores what Microsoft (MSFT) is up against. Because, sadly, the thinking inside the company appears to mirror that of a small cross-section of commenters who do not seem to think a profound shift in thought needs to occur. Or, more specifically, do not consider the direction the CEO search (and hiring) takes the single most important factor that will impact the stock going forward.

Of course, it could be that the reactionaries didn't take kindly to my use of the term "loser."

Get a grip.

When I write these articles I pretend I'm sitting next to you at a bar, attempting to make my case, relay some information or both. A formal approach would only cloud the path to understanding.

Today, Microsoft sits at a crossroads.

Tomorrow (not literally), it will name a new CEO. The choice Microsoft makes will set it on a course. Two of the most probable directly relate to the situation -- past and present -- at Yahoo! (YHOO):

  • Like the pre-Marissa Mayer Yahoo!, Microsoft runs through five CEOs in five years; or
  • Microsoft makes a bold choice, like Yahoo! did with Mayer, hiring somebody who will walk into the Gates/Ballmer-decorated executive suite and knock some damn pictures off of the wall.

Microsoft isn't all that different than Yahoo! was when it hired Mayer, even though its outgoing CEO is coming off a long and shockingly stable tenure.

They're similar because there's lots going right with the business.

Where Yahoo! has always had traffic and an ubiquitous presence, Microsoft still dominates consumer and enterprise spaces with a massive Windows/Office installed base. Albeit for different reasons, Yahoo! has been able to rely on a strong cash position and pretty solid balance sheet. Microsoft is even stronger in that regard.

But Yahoo!'s board and CEO search committee realized it had to kick the heroin habit. It could no longer uncritically consider all of the above as things it had going for it; rather, it had to go to another extreme, treating these positives as having overstayed their welcome. If the company didn't move aggressively to change its culture and shift strategy, it would, at some point, devolve into irrelevancy.

That's, for all intents and purposes, where Microsoft finds itself.

And, if you consider the candidates up for the gig and observe the concern that one got away, you have to believe it's set to hire an enabler CEO. Somebody who will facilitate the status quo with empty talk of change, managing business as usual and overseeing the downfall. 

If you don't think this qualifies as a "loser" strategy to hire a "loser" CEO (in the most loving and street slang sense of the term), you're wearing the same brand of blinders Blackberry (BBRY) faithful had on before that company's all-out collapse.

Cash. Installed bases. Reputation. Traffic. Tech that you consider impossible for enterprise (and some consumers) to unwind. These are not signs of a healthy business when they're pretty much all you have to hang your hat on. (I say "pretty much" because Xbox is an incredible franchise, that, sadly, Microsoft fails to take full advantage of).

That last one -- Tech that you consider impossible for enterprise (and some consumers) to unwind. Though I don't know her, I presume that's something that would make Marissa Mayer physically sick. The notion that you somehow weaseled your way into the life of your users and, like a mooching boyfriend, you can make it hard for these users to extricate themselves from a less-than-ideal situation.

That was basically what Blackberry hung on to ("security" was their security blanket) as it refused to hire a flame throwing CEO and incite meaningful change. Now Microsoft appears set to do the same. And some readers take exception to the focus on the CEO search as pivotal, of paramount importance and, as it stands, the stuff losers are made off.

But, remember, what you read in the comments section of a financial media article does not represent consensus. Others do exist who get what I'm saying loud and clear:


I'm not holding my breath that Microsoft will.

--Written by Rocco Pendola on an airplane somewhere over the Northeast over the weekend leaving winter weather behind en route to LA!

Rocco Pendola is a columnist for TheStreet. Pendola makes frequent appearances on national television networks such as CNN and CNBC as well as TheStreet TV. Whenever possible, Pendola uses hockey, Springsteen or Southern California references in his work. He lives in Santa Monica.

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