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We haven't adopted any yet but we have done long term for teens for many years and taken guardianship of one.
There's lot of things we went through and finally settled into the most simple things. The question I always ask is "What do you want us to know about you?" He'll then ask the same. Then you can start asking what you want to know and what he wants to know that you haven't covered. You don't need to know everything all at once.
I would ask him similar things about rules. What rules has he had that are not necessary - things he would not do or do anyway. What rules are good, OK etc. Then what rules does he hate. Many of these guys come from places where the rules are inconsistent so make sure you communicate well to avoid the appearance of inconsistency. Explain the purpose of your rules. They usually reflect your family values. Rules are naturally relaxed as trust builds so stress that he is truthful, tell they whole story accurately. Accept mistakes and learn from them.
I like to meet at the end of every day and ask about how the day went and what tomorrow is going to be like. Some boys are huggers and some are not. Ask him.
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