Never tell your teen you want to talk in from of other people, except perhaps your child's other parent or guardian. Take your child out to a coffee shop or for a drive, away from siblings and distractions for both of you. Avoid going to a place where either one of you may run into someone you know. You will get answers if you set up a comfortable environment and listen respectfully.
Q: What should I hope to get out of the conversation?
First, you want to have a productive conversation. This means that through the process of your conversation, you want to support your child and confirm that you are a good resource and a nonjudgmental listener. Second, you want to give your child realistic strategies for confronting the problem effectively. You will never accomplish the second goal without the first.
Q: Are there any other nuts-and-bolts tips on having the actual conversation?
Share your own experiences, especially the ones when you were your teen's age, made mistakes and learned from them. Avoid talking about what you have recently experienced, because you need to maintain boundaries—they need a parent figure now, not a friend. The hard reality is that you can't always fix things for your kids. You can only try to give them the skills and support that set the foundation for doing it themselves.
Q: How can I tell if my teen might want to talk to me?
Anytime your teenager wants to talk to you, drop everything and pay attention. Watch for signs of your teen wanting to talk, such as if your teen hangs around where you are but doesn't necessarily say anything, or if your teen says he or she doesn't feel well but there doesn't seem to be anything physically wrong. Notice if your teen tries to get you alone, away from others—for example, if he or she volunteers to drive somewhere with you in the car. If your teen wants to talk to you but also couches it as "no big deal," don't believe it. Just by bringing it up, he or she is already telling you that it is a big deal.
Start having the dicussion now! Ask the questions.