One mom of a 2.5 year old recently asked how best to encourage her son to be less shy. In my talks to parents and teachers, I cover four basic boy types. One of them is called “Shy-Vigilant”. These little guys tend to pull back when around other kids and don’t jump into play. They love to run behind their parents and watch what’s going on. This boy holds his preschool teacher’s hand a lot of the time, but otherwise he is doing well and listens and behaves in that setting.
At 2.5, there’s no telling how much of this boy’s shyness is set in stone. So much development is on the way in the many years to come and kids change all the time. I did recommend a buddy system approach to help him feel more at ease at preschool. Maybe there’s a boy (or better yet maybe a girl, as these type boys like less stimulation) who could be paired with him some of the day around an activity or two. This boy could get a simple reward (a checkmark or colorful bead to add to a cup) for spending more and more time not holding his teacher’s hand and more time with his new buddy. This could be encouraged slowly, with longer times being expected.
Another good strategy is to have a classmate over to his house. I’d make it a time-limited and low-stress visit that’s impromptu – the other mom and classmate can just show up for a “visit” and then see how it goes. He’ll be on his territory, so that should help him feel less shy. And not announcing it or planning it will help him be less worried.