Chip_ConleyIf you follow social media news, you’ve probably heard about Chip Conley, the 48-year-old CEO of Joie de Vivre, a 3,000-employee company that runs a collection of boutique hotels in California. Apparently Conley likes to get personal on Facebook and Twitter. On Facebook, he posted pictures of himself at Burning Man, shirtless, donning a tutu in one photo, a sarong in another. On Twitter, he’s lamented about the breakup of his eight-year romantic relationship.

Conley’s propensity to lay his life bare online left some of his younger employees confused, not to mention a tad concerned. This doesn’t surprise me. Career and social media advisors have been browbeating Gen Y about slapping racy, drunken photos of themselves on the web for years. Every time another twentysomething gets fired for inappropriate blogging or Facebooking, it’s a national news item.

When word of employee concern got back to Conley, his first instinct was to tell his head of HR, “Screw that. People who don’t like it can go work at Marriott.”

Then Conley got more contemplative — in an op-ed for business site BNET, of course.

There, Conley outlines his company’s social media policy. Employees can’t post pictures of or tweet about guests staying at the company’s hotels. Nor can they reveal the business’ trade secrets. Likewise, employees stupid enough to post online photos of themselves stealing street signs — while wearing a Joie de Vivre T-shirt — may have an unpleasant meeting with HR in their future.

But, Conley writes, “What if pictures emerge of a desk host drinking from a beer bong at a football game, or decked out in an S&M getup at an underground club? I’d have no problem with that, although I know plenty of CEOs who would. To me, that’s an employee’s private life.”

So the boss is cool. Bonus for employees who like to document their beer bonging and S&M apparel online. But what about customers? Or investors? For Conley, this doesn’t seem to be an issue. In his words:

“No one complained when I dressed in drag at a holiday party seven years ago, although pictures never made their way to the web. And I doubt anyone would be complaining if my [shirtless] pictures were from a beach vacation.”

He raises some interesting points. When it comes to online reputation, why should we hold CEOs to a higher standard? Aren’t employees clamoring for more transparency from their executives these days anyway? When does a vacation photo cross the line, and who’s to say Burning Man is a less appropriate vacation for a CEO than a trip to Club Med? As Conley muses, “What, exactly, does it take to damage the image of the company?”

The worker bee in me recognizes the plusses of being employed by a guy who’s open-minded about social media use. No more asking friends to take down Facebook photos of me from my college kegger days in the 80s, just to be safe. No more worrying about what the boss would think if I ever decided to publish a Harlequin bodice ripper or a piece of erotica under my own name.

But the cautious professional in me isn’t so sure. What if Conley’s business has a change in financial circumstance and he finds himself needing new investors, branding partners, or the patronage of some of the country’s more conservative populations? Will his “take me or leave me” Mr. Authenticity shtick still hold up? Or will he regret having posed in a tutu for all the interwebs to see?

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