One of my former guilds had a problem with event scheduling. Peak activity was 8:00pm to midnight realm time, but the GM kept scheduling events at 6:00pm because that was most convenient for him. Between the timing and the GM's mild case of Gearscorephilia, events frequently got cancelled.

On a similar note, leveling guilds should try to include activities for characters who aren't at max level. It'll be hard to find a decent-sized group for battlegrounds, but dungeon runs are good group-building activities. I don't mean the kind where an 85 drags somebody through Scarlet Monastery five times in a row because he doesn't want to do the work; I mean hopping on an alt and running the Graveyard together at level 30, the way Blizzard intended. If you and your officers don't have lowbie alts, create some. Tank- or heal-capable classes are good for filling those hard to find roles, but don't forget to read up on your abilities and class changes. An heirloomed level 40 alt takes a /day or two to set up, and has access to seven distinct old-world dungeons through the Dungeon Finder (more if you count the multiple wings of Dire Maul, Scarlet, and Maraudon).