wow this really bugs me

So for our schedule at work, only two of us stay until closing on the phones team-me and this other guy, i'm going to call him bobby. Bobby is a really nice guy, he's a good worker, but sometimes it seems like he doesn't completely understand or pick up on some things about our jobs. When dealing with our customers ,we have to be pretty detailed as far as when products will be delivered to them, etc. One of our products ships standard overnight, but does not ship over weekends, so if it is ordered on a Friday, it will actually go out on Monday for delivery on Tuesday. He did not explain this to a customer and she was expecting something on Monday-fortunately for her, she called back with the same order later that she needed for Tuesday-she had something planned for Monday where she needed her product and had she not called back and gotten me (I was the only other person there..so not JUST me, but me at that time) she would have had that group of people come, but no product, ruining the thing that she had planned. I don't understand why he wouldn't specify that it was actually Monday for Tuesday. Our customers deal with very sick people and we deal with very much lifesaving drugs..we also deal with strict timelines-for our customers, literally if the package isn't there the minute we say that it should be, they start calling us to track it, worried that it didnt go out and won't get there-why would you not specify , especially when it's a day off..like saying on a Friday htat something will ship overnight would also make me think of Monday..he said that she "must of assumed that it would get there on Monday" but who wouldn't? He also always logs off the phones like 2-3 minutes early, so if there's that ONE last minute call right at closing, I ALWAYS get it...and more often than not, it's a long request or very intense order, or something that might keep me there half an hour later..which is super annoying (worth it) but annoying..he also rarely volunteers to stay late or come in early (which is fine, i know that's personal choice and regarding his own schedule) but just to me, it seems like he doesn't really care that much...but then again, I'm the crazy who will come in early or stay late whenever I can, but i like to make any extra money that I can..need to support my lifestyle haha...

It's also super irritating that some people don't put notes in the accounts regarding phone calls that they had with customers-it sucks when other people's mistakes fall on you..or just non specific notes...we get some customers with attitudes and when notes and call logs are missing, they just get even more angry, which though annoying and frustrating, is understandable.