i have a lot of experience of leading large groups into battle on Siege. i don't claim that we have always been the winners, but on many occasions we have, even though we never used mounts and had very strict template restrictions (all dexxers, only about 2 mages, no ninjas, no samurais, no nekros, no paladins, etc.)
back in the days we used to have about 20-30 people online at the same time and as some others already stated: this is when it gets REALLY hard to lead and organize them. splitting those people up is a good idea, but i never really liked that, because you basically had to avoid each other and get separate uoam channels then, since people got confused and all of a sudden ran with the other group without noticing.
so i stuck to the 'one group' principle.
here it is important to have ONE person call the shots! this is the only thing that works. that person needs to have a unique color in UOAM that everybody can read and that noone else is allowed to use.
everybody in the group has to obey the leader, no matter what. you can discuss things later, but in battle you HAVE to follow the orders given by the leader.
everybody except the leader only talks in UOAM when necessary (report incoming opponents, report own death, etc.). otherwise it gets too confusing for everybody
stay together at all costs! that means stay within one screen, so everybody can see everybody else. i used to wear special clothes, so people could always recognize me and thus try to stay on the same screen as me at all times.
Crossheal ! it is faster than healing yourself and multiple people can help heal you through massive manadumps for example. here it is important for the player who is being damaged NOT to run away. he has to basically stay in the same spot, so people can heal with bandages (in case you only have very few mages). Also it is more important to keep your buddies alive than to finish some opponent (depending on the number of opponents of course).
ok, those are the basic principles that always apply. now for practicing.
get all of your guild together and make them get OFF their mounts. all of the above gets alot easier when practiced without mounts because mounted players have a tendency to run off the screen, thus splitting up the group, making it possible for the opponents to pick single targets more easily.
now make teams that PvP against each other.
each player should have a makro that indicates when he needs healing, so the others can help him in time. (e.g.: we all used to have a makro saying *xxx bleeds*.)
Let the teamleader call the targets. as soon as he called a target everybody in the team attacks that target until it is dead.
practice teamfighting that way until people really work together. then give them their mounts back and practice again. try to make people really stay close to their leader. after a while your group will get better and have a large advantage over other groups that are not as organized.
all of the above is for guilds that only use UOAM as means of communication. we never used anything else, because i didn't like my roommates waking up at 4 in the morning to me yelling at my computer hehe.
ventrillo or teamspeak make it alot easier for the teamleader because he doesn't have to type all the orders, but it appears i was a fast enough typer most of the time, so it can be done, believe me.
but still the basic rules apply, also when TS or vent is being used.
any further questions? just ask...