If there was a parent constantly late to check out the first thing I would do is bring it up in conversation, “I’m sorry to see you’re running behind I understand that can be stressful! Is everything okay?” After attempting to gain insight I would then offer help is necessary, ” I could see how that can be stressful, however, pickup time is… is there anyway I can help to make it so that our friend is getting picked up on time and not having to hang out here by themselves? I would then attempt to create a plan to help or perhaps change the pickup time. If things were not resolved I would then contact my supervisor to discuss further plans to help both the child and parent succeed.