Identify the root of your children's shyness. Some children are uncomfortable in groups, while others feel shy talking to people one-on-one. Once you identify the root, you can better pinpoint activities that will help overcome your children's shyness. Be a positive example to your children. If they see you "acting" shy, they may do the same. However, if they see you engaging other people in conversation and making an effort to be sociable, they'll be likely to emulate that behavior.
Give positive reinforcement. Shyness sometimes develops out of insecurity; children can feel insecure if they're often criticized or berated. Whenever your children do something good, be sure to compliment them, which will help to build their self-esteem. If they makes mistakes, let them know that everyone makes mistakes and that no one's perfect. Shy children are often afraid to make mistakes for fear of being ridiculed, so it's important to let them know that mistakes and, even, failure are part of learning.
Practice social skills by role-playing. This is a fun way to teach shy children what to say to others in particular situations so that, when the time comes, they'll know what to say. For example, you play the host of a restaurant and your children play customers. The customers have to tell the host that they need a table for two people. After that, you can play the role of the server and take your children's orders. Practicing social skills at home can help children feel more confident when they're out in the world. For example, have your children make "pretend" introductions of family members to new people; this gets the whole family involved, making it more fun. Another exercise is for the whole family to spend the day paying each other compliments every time they see each other. This will teach your children that saying something positive to someone is a good way to initiate a conversation. This particular activity can be practiced on a regular basis. If an activity is fun, your children are more likely to want to do it.
Enroll your children in activities they like. It's surprising how children will blossom when they're doing things they enjoy. "Social" classes such as dancing, karate, art and athletics help teach social skills because kids are engaged in enjoyable activities with other kids. Ask your children what types of classes they'd be most interested in and do some research. Consider auditing classes so that your children can observe them beforehand and decide if they're something they'd like to do. Be sure to observe the teachers who'd be in charge of the classes; some teachers deal better with shy children than others.