We have many rented pastures so not many working facilities. Have to haul them back to the main barn. We set up portable pens, with panels to divide them, so there are 2 or 3 pens, one leading into another so you can pen the early cows in then open up and get the stragglers in. Will feed in the pen for a few days beforehand and we still have a few that are wary. Mostly anything raised here knows that being called in means feed. The bought ones are the tougher nuts to teach but if they are a problem after a few seasons they will go. Mostly have the person that does the checking go to get them in and then the one driving the trailer bring it up after they are in.
Have one place that the rotational grazing goes through a big open area and so we set up a pen there and then they have to go through the pen to the next pasture. We usually don't have more than 40 cow/calf pairs but still a sizeable group.
Lately have been calling them into the first pen, opening the second pen, letting them in, closing the gate, giving some good hay to keep them quiet when we try to get in the rest into the first pen. Often is a few calves that are the problem, or one cow and she will take a few calves off with her. That cow will then be delegated to a pasture that has a good system to get the cows in and if she has good calves will spend the rest of her life in a place where she can be gotten in more easily. Otherwise, she will leave. We always try to have the pen set up where they have not been able to get to the grass so it is also a temptation to just eat once the grain is gone. We will use 5 gal buckets and always try to have twice what we need with us in case.... but for the most part, one of us can get them all in in a very short time. They just have to get the routine down. And yes, doing it the same time of day, in the same way makes a difference with the wary ones.