Of course you want to take charge when you think your kid is making a mistake, but that's not always a wise move. Below, six tough-call situations, along with expert advice on when to step in, when to back off, and how to help your teen master the art of the smart choice.

By Emily Listfield

My daughter Rachel, who graduates from high school this month, informed me she's going away for a weekend with her boyfriend. I've told her it's out of the question, but she says I can't stop them because they're 18. Help!

It's totally life-altering when your kids come of age—and it's rarely a smooth passage. Suddenly they're old enough to vote or enlist, and many take advantage of this moment to flaunt their newfound independence. This situation is even more fraught because Rachel's throwing sex into the mix. As long as you're not worried about her safety, don't drive a wedge into your relationship over this trip. "Use this as an opening for a deeper discussion about the important decisions that come with adulthood, and how to make them wisely," says Roni Cohen-Sandler, PhD, author of Easing Their Stress: Helping Our Girls Thrive in the Age of Pressure. "Look at it this way—your daughter is giving you a chance to do that while she's still under your roof."

My daughter is a shy 11-year-old who refuses to enroll in a single after-school activity. So much alone time isn't good for Chloe, and joining a class might help her make new friends. Is it wrong to force her to sign up next year?

Taking charge is the right course, but don't make a unilateral decision behind her back. Explain that extracurriculars are an important way to socialize and explore various interests. Tell Chloe she has to enroll, but let her choose the program. Your ruling will go down easier if you can discover what's behind her reluctance. It's possible she has a hobby that isn't included in after-school programs; in that case, suggest a similar class where she might meet other like-minded kids. However, if you suspect she's very uncomfortable being around her peers, "social anxiety may be fueling it—and therapy can help," says Neil Bernstein, Ph.D., author of How to Keep Your Teenager Out of Trouble and What to Do If You Can't. "The best way to find out is to speak with her school counselor."

Talk about overcommitted—my 17-year-old always enrolls in too many Advanced Placement classes. He says he loves them all, but I worry that he's spreading himself thin. Should I tell him to ease up this fall?

With so many kids burning the midnight oil, it's just a matter of time before AP syndrome becomes a recognized diagnosis. Before you put on the brakes, take an honest look at how your son is handling it—after all, this is about him, not you. Many teens thrive on overdrive. "Assuming your son isn't feeling continuously stressed, his multiple commitments are fine," says Carl Pickhardt, Ph.D., author of Surviving Your Child's Adolescence. Keep a close watch for burnout: Is he getting sick frequently or feeling anxious? If he's buckling under the pressure, consult with a school counselor and work together to help your son lighten his load.

I hate being a nag, but my 12-year-old, who's been taking piano lessons since she was 4, never practices unless I make her. Even then, she puts in the time and nothing more. When I told her it was okay to stop, my daughter said she wanted to continue, but she still doesn't practice! I don't know what to do.

It's time for a heart-to-heart. "Since she doesn't want to opt out, she must be getting something positive from her lessons, and you don't want to walk away from that," says Cohen-Sandler. "But it could be she's afraid you'll be disappointed." Reassure your daughter that there's no shame in quitting if she's lost interest. At the same time, make it clear that you won't continue to pay for lessons unless she practices and strives to excel. It's a good idea to ask the teacher to weigh in, but you and your daughter should decide together. Even if she stops playing, remind yourself it's not a final decision; she can always resume lessons and pick up where she left off.

My 15-year-old, Stacie, has a new BFF who's always in trouble, smokes and hangs out with older kids at parties I would never let Stacie go to. I'm really tempted to ban the friendship, but will that backfire?

One of the toughest things about parenting teens is the realization that—big sigh here—you can't choose their friends. And difficult as it may be, you can't even criticize this bad girl because that will only make Stacie dig in her heels. "Take comfort in the fact that adolescents often gravitate toward 'more adventurous' peers so they can learn about risky behavior without engaging in it themselves," says Pickhardt. "You and your husband might tell her, 'We're okay with you hanging out as long as you don't act the same way, but you have to be honest with us.' You'll establish trust and keep the lines of communication open."

David, my 14-year-old, made the school baseball team even though he's not a particularly strong player. He's okay with spending most of his time on the bench, but I'm not. I want him to join track next year, where he'll actually have a chance to exercise—and compete. Can I overrule him?

Your son may not be not an all-star, but that doesn't mean he doesn't love the sport and the camaraderie. And David is getting a workout during practice. While you should respect his feelings, there's nothing wrong with having him write down the pros and cons to be sure he's thinking things through. "Ask him neutral questions, such as 'What do you like about baseball?'" says Cohen-Sandler. "Maybe he enjoys hanging out with the coach and his teammates, which is a good reason to stick with it." Should David decide to switch, show him support. "Kids can be embarrassed to admit they've had a change of heart," says Kay Abrams, Ph.D., a Maryland-based psychologist who specializes in adolescent parenting issues. "Responding with sympathy or humor is always better than saying 'I told you so.'"

The Art of the Smart Choice

It's a fact: Adolescents are more likely than grown-ups to make impulsive, emotional decisions. That's because the teen brain—specifically, the not-yet-mature prefrontal cortex—isn't fully wired for thinking ahead or sizing up risks and rewards. Here's a five-step plan for parents to help kids develop a better skill set.

Let go. After years of calling the shots, make sure you're truly ready to back off and let your child take charge. The transition from "Because I said so!" to "What do you think is best?" is one huge, scary leap.

Take opposing sides. Ask your teen to spell out—orally or on paper—the upside and downside of the issue at hand. It's fine to point out a few pluses and minuses he can't come up with on his own.

Be a sounding board. Your kid might get mired in details and lose sight of the big picture. Listen to her thought process and help her refocus as needed.

Hold your tongue. It will take all your willpower not to jump in and say, "I think you should...." Remind yourself that the goal is for your teen to make an informed decision, even if you disagree.

Reflect and regroup. Have a sit-down and ask your kid to evaluate her decision after the fact—what worked, what didn't, what she might do differently next time. No judgments or criticism allowed.

Originally published in the June 2014 issue of Family Circle magazine.