"Making things hard for them" implies penalties or punishment. Penalties are okay for the right reasons - the guard is on high alert, doesn't like Orks, you don't look like you belong there, you are carrying three Assault Cannons, etc. - but penalizing someone because they're trying and just aren't there, yet, is obviously a bad call.
As for another player being better at it, that kind of thing needs to be worked out during CharGen and team creation. If, in the examples above, I throw a couple of bonus dice to Example 2, and he is playing anything but a Face, he's still not going to be more effective than a Face who rolls their base dice pool.
Unless the Face is a total gimp, their Social dice pool should crush that of any other teammate. A Heavy Weapons Troll doesn't out Con a Dryad (extreme example, but you get my point). A team certainly shouldn't have two Faces, in most circumstances, and if it does, they should have complimentary Specializations, not overlapping ones.
People have natural strengths and weaknesses, and they don't necessarily coincide with those of their character. Some people will gravitate toward certain roles, while others will branch out and try things they might not be great at. If someone is trying to play a role well, I'm going to encourage that.
-Jn-
Ifriti Sophist