The easiest way to get your children accustomed to speaking to others, whether it be fellow kids or adults, is to talk with your kids as often as possible. By often I mean all day, every day, at every opportunity.
One great place to utilize conversation on a daily basis is the dining table. Because we are a society of multi-taskers a family can eat, get a handle on table manners and learn the art of conversation all at the same time. If you, as an adult, don't feel you're much of a conversationalist have no fear. With kids you don't have to say much. All you need to do is learn to ask the right questions.
Begin by asking your kids about themselves. You can start with, "What's the coolest thing you did today?" While they answer your question show enthusiasm in their descriptions and maintain eye contact with them. Be engaged and actually listen to their answers. Don't allow your phone or a television to distract you. All electronics should be off. While we want to multi-task, those darned electronics result in the opposite of what you want to achieve. Oh, did you forget already? We are discussing how you can teach your kids to better interact and carry conversations.
While your children are answering your questions, chew with your mouth closed and encourage them to talk when they don't have food in their mouths. Don't interrupt them, but do ask at least one follow-up or clarification question. This lets them know you are paying attention and that you really care about how their day went. You could say, "Wow, sounds like you really enjoyed riding your bike today. Is there somewhere you'd like to ride to with me sometime?"
If you have more than one child ask similar questions to each one. Allow them to answer. Show interest. Smile. Make eye contact and make sure the other siblings are listening, not interrupting and paying attention as well.
These are easy first steps to teaching your child how to feel comfortable when they are speaking to others. First you are establishing eye contact. This is something when they see it done by you, they will do the same. It may sound extremely basic, yet you would be surprised how many kids and adults have no idea how important looking someone in the eye can be.
Second, at the dining table you are teaching manners by not chewing with your mouth open. You are chewing, swallowing and then talking. Your kids to learn to not talk with their mouth full when you are doing the same.
Finally, you are teaching your children the valuable skill of asking questions about others. Kids are curious people. They want to know things. They are never going to stop asking you "why."
Talking about themselves is another animal. It can be difficult for a young person to articulate certain aspects about what they do and how they feel. When a child feels comfortable conversing about their day and the fun they had at recess, emotions they may be feeling become easier to realize and talk about. As kids get older, they will want to tell you about difficulties they may be having. If, however, they don't have a history of discussing how their day was, or describing their anxiety about a test or going to the dentist, they may not be able to articulate how they are being bullied, feeling frustrated or even feeling elated. As a parent, the easiest conversation starter you can initiate with your kids is to ask a question about them.
Teaching the art of conversation to the young is incredibly important. Eventually, as kids get older, they get all quiet and sullen. If they are schooled on how to talk and ask questions at an early age, they will be less likely to clam up during their adolescent years.