Darn, I thought you were just looking for interesting stories. I never really admin asst'ed, I worked at one place where he practically had all his employees as his admin but I seemed to get a lot of the tasks, and another where I would backup the big boss's admin when she was out.
For that second job, I don't know what would have helped other than a calendar program she could scribble on. You have no idea how much paper I wasted printing out her daily calendars. Not just any paper, it had to be in color. Not just the daily calendar, folded in a trifold, but also her weekly calendar, and the monthly calendar so she could see the changes made to it during the day. Sigh.