Here are a few things I’ve done over the years to encourage the child who is timid/fearful because of insecurities, perfectionism, or sometimes stubbornness.
Get to know the child on a personal level. Hold informal conversations with them before school, at lunch, during recess. Ask about their puppy, or their baby brother, or if their rabbit had its babies yet. Tell them you saw their mom in town yesterday. Converse with the child outside of school (like at church) if this is appropriate. I believe that all children enjoy the recognition this brings even if they find it hard to reciprocate.
The other year we were working with a child who did not like to be wrong. They also found parts of school difficult. Socially they were a little awkward. When confronted with a hard part in their school work, they would sit frozen, stare in space, and refuse to work. The teacher gently insisted that they at least raise their hand and request, “Can you help me please?” We also held private conversations with the child and let them know that they cannot be helped if the teacher doesn’t know what is wrong. It took a while but with gentle pressure, the year ended with a much more confident child.
If fear of being wrong/making mistakes is a big part of the problem, let the child know that making mistakes is part of who we are. I make plenty of mistakes in the classroom and I sometimes will actually call attention to the fact that I made a mistake–just to let students know that even grown-ups don’t have it all together. Helping a child realize this is not a one time done deal. It is an on-going process.
I write this next part cautiously because I do not know all situations and I do not want to do more harm than good…but sometimes the “root” cause for shyness is stubbornness. Or maybe a better way to say it would be that because a child is shy, stubbornness (and pride) stand in the way of breaking through the shyness barrier. I say this from my own personal experience growing up. As an adult, looking back, I’ve been grateful for every time I was “forced” to go beyond my shyness and perfectionist tendencies.
However, you deal with this, deal gently, deal lovingly, and deal prayerfully.