When you are giving your child a new privilege (for example, crossing the street, going to a friends house to play, increasing a curfew), do it in stages.
Crossing the street: First let your child cross with you. Have her make the decision about when it is safe and give you the “go” signal. Once you see she makes the right decision every time, set a limit on how far on the other side of the road she is allowed to go. Gradually let her go further as she proves she will follow the rules.
Playing at a friend’s house: First, go with him a few times and visit with the friend’s parent while the children play. Have the friend come to your house to visit as well. If all goes well, arrange for him to have short visits alone a few times. If that goes well, you can arrange for a bigger block of time to visit. Be sure to have the friend visit your house as well, so you can be aware of how they get along and what they do with there time.
Increasing a curfew: First, increase it by a small amount. Make sure he is meeting his curfew every time and staying out of trouble while he is out. When you think he is ready, you can add more time for special occasions.