Right, clashes depend very much on what you add. To use your example, it depends - not very helpful, but true.
If you add a head pack that adds completely new heads, there shouldn't be a clash. If it's two mods that both alter the stock heads, there will be a clash. This isn't fatal though - what happens is the last mod you loaded will take priority and be the one that is used. So, if both mods alter head A, it'll be the mod that you paste the file in for last that is used. This is because the files for that head will be overwritten when you add the new meshes/skins/whatever to the data files area. If you're talking about one of Westerly's packs, they go fine with everything. I've got mixed feelings about some of his hairs though. It's odd when NPCs all over the game suddenly sprout emo-fringes. Especially the Khaijit.
For other clashes, most of the really big mods offer comparability patches to smooth things out, or at the very least will offer advice in the readme as to what will or won't work with their mod. When it doubt,
always consult the readme. If that doesn't help, try to contact the author or open a thread here. Most mods will work together, apart from obvious things like if you use two alternate beginning mods, or two house mods that are in exactly the same place.