Boss, we'll discuss it on Facebook ... next to the lingerie ads

If you don't want ads of women in panties next to your job discussion board, congrats -- you've just found the flaw in Facebook advertising. Alex Iskold has written a brilliant analysis of the problems with Facebook advertising, which boil down to three things: Facebook doesn't really know us, its data is not well structured, and users of social networks aren't there to click on ads.

The combination of these failures is why Alex recently saw the above ad as he conversed with colleagues online. He notes:

The (Facebook) site does not really know what I like. It does not know my book tastes, does not know that I am running a startup, does not know that I like Cabs and Pinots. It does not know that I am a Netflix user, that I am increasingly less tolerant of cold weather, or that I have 3 beautiful little daughters.

So Facebook does not really know sophisticated things about me. But even basic information that it ought to know is beyond its grasp. For example, if I add the Flixtster application and start displaying movies that I've rated on my profile you'd think that Facebook would learn that I like movies. But it wouldn't. Facebook's system has no idea that the Flixster application is about movies and has no idea what kind of movies are being displayed.

There are many other problems, especially the unexpected hostility over the Beacon news feed ads which alert all your friends that you've just bought jock itch ointment. Facebook will figure it out. Until then, the social party at Facebook remains miles away from the cash register at the mall.