I am assisting in a two year old class room this year. We have all personality types in our classroom and all personality types amongst our parents. The first two weeks are always hard as our kids get used to drop off. You can always tell who is going to be fine though by how the parent handles it. We have one dad who just does not want to go. He is sure his son cannot handle it. He spends 15 minutes saying "daddy is going to work okay?"
As someone who works in the classroom please believe me when I beg you "PLEASE don't do this!"
By saying "okay?" with a question mark you are asking your child's permission to leave. Please do not do that. When you are ready to leave please matter of factly tell your child it is time for you to leave. If your child is prone to being upset let the classroom workers know just before hand. We will hold your child, we will hug your child, we will reassure your child. I personally prefer to just scoop them up (unless they don't like that and some don't) and hold them and say "daddy will come back" until they are calm.
Secondly, the longer the dropping off parent stays the more time they are giving their child to work up into a tizzy. Essentially they are enabling and encouraging their child to throw a fit. Some parents really seem to need this validation that they are the most important people in their child's life. It really isn't fair to the kid.
Thirdly. We expect some children to have separation anxiety. We work it into our day in the classroom routine. However, after about 15 minutes we are ready to get on with our morning. The longer the parent prolongs the good bye the more disruptive it is to the other kids in the classroom. Remember, we love your child; and we do. We love our kids in our classroom. But in my classroom there are 9 kids. If your child needs to be comforted when you leave and you wait 20 minutes to leave and it is time to line up and wash hands and go to circle... I cannot hold your child. I have 8 other kids to help find circle time. They are two year olds. It is like herding cats. If you only stay 5 minutes, then chances are good I can devote between 5 and 10 minutes to your child to get your child calm and ready to enjoy their day.
There is a little boy in our class who looks like my son looked when he was 2. He loves school but he is very attached to his mom. The first week of school he started getting upset during the last 30 minutes of class. So I picked him up. He let loose and sobbed, heart wrenching, sobs. It was awful. Since then mom has gotten less and less strong about leaving. Today she stayed but she wanted to sneak out so he just cried and whined the whole time. He was miserable. The class was miserable. It was awful. Please don't do that to your kid. Either leave or commit to staying and tell the kid you are going to stay. They are little. If you just want them to play with someone their own age and you don't care - then stay. If you need 2 hours by yourself for your sanity then make a break for it. But don't drag it out.
There is a little girl in our Monday class. She is sweet and very strong in personality. She does not like change and she does not like not to be in control. Her mother is delightful. Her mom knows it is hard and she holds her daughter and helps her find something engaging and stays very calm. And when mom is ready to go she looks me dead in the eye and nods her head and I move closer. And mom pulls her daughters arms off of her neck and hands her daughter to me. She calmly says goodbye and walks to the door. She does not say "okay?" she does not look back, she does not stop. Her little one is upset for a few minutes but she likes books and is happy to sit in my lap and read a book until she is settled and then she goes and plays. I wish this mom could give drop off lessons.
If you are new to the preschool or kindergarten routine I highly recommend a sweet book for you and your little one to share together.
It is called "The Kissing Hand" by Audrey Penn.
One of our preschool teachers shared it with her class. Even though neither of my boys had ever shown any reluctance to go to preschool they each heard that book in their 4 year old class (their last year in preschool) and loved it. Per the book, we kissed hands every drop off for the rest of the school year.