For most skills, some people attain a level of art which surpasses describable taskification. If you asked a professional athlete how he throws the ball, or how he runs, he might mention a few tricks, but he's not going to be able to communicate it to you; in his mind, he just does it. I coach a top university speech and debate-type team (Mock Trial); I find it easy to describe how to do basic things, but nearly impossible to describe how to do sophisticated things; it has to be demonstrated and the students have to understand it themselves, and many of them fail to do so.

To some degree, socializing works on the same level. If you're thinking your way through each step, it's going to be perceptible and you will seem awkward. To seem natural, you need to simply do. That, I think, is the meaning of statements like, "just be yourself" - if you're consciously executing some series of actions that are not natural to you, you will always be thinking and never just doing.

Of course, the challenge lies in getting to that level of comfort. I'd think your best bet is exposure, ideally via both popular media and just getting out of the house. It admittedly might help to start off with some taskified strategy, since even if it is awkward, it may be less awkward. But I think the overall attitude opposed to taskifying social interaction is the fact that social interaction, at the "artisan" level, is not describably taskifiable.