According to empoweringparents.com, poor self-esteem comes from running up against adversity and not understanding how to recover from it. Just as you need preparation for an interview your teen needs preparation to face the challenges so often found in the places they go: school, the games pitch, the choir, the band, the place where the volunteer....You shouldn't expect them to know how to deal with it without any training. Yes, they need training to learn how to recover from adversity. So, you can give your child opportunities to fail and succeed in a safe environment.
When I spoke to 14, 15, 16 year olds last Saturday, all of them said, in different words, that their greatest fear is 'not succeeding'. They need to know that they can recover from failure.
This does not mean that you take on and fix their problems for them. Some parents will pick up the phone and apologize for their child's behaviour. Let him take responsibility and apologize himself. You're not going to apologize to his wife for him, are you? So train him now-otherwise he's going to go out into the world and not know how to deal with things. Remember, your job as a coach is not to step onto the court-it's to coach from the sidelines. Just remove yourself from the court. You're not doing your child a favour by playing the game for them. Parents sometimes get in there because they want to help, but if you're doing that, ultimately you're handicapping your child.

Coaches prepare the team before game time. Everyone might practice hundreds of hours for a 90 minute game. The team goes out there, they try some things, they do some things well, and they do other things poorly. And then the coach breaks it down at half-time. "All right, here's what's working; here's what's not. What do you need to do this better? Don't shut down, you're going back out on the court, but how could you improve? How could you take this to another level? How could you deal with this in a different way?" That's what a coach does and that's what you need to do as a parent with your teen's self-esteem.
And if you are troubled by their silence, here are some techniques to open up conversations:
Take the lead and ask your teen to talk to you about what's hard. If you can talk about the hard things you faced in your life when you were a teen, it makes you vulnerable. In return, there's a good chance your child will feel comfortable being vulnerable to you.
Use movies to start conversations. Teenagers are most vulnerable after they've seen something that moves them or brings up an issue in their lives. Movies work really well as a neutral conversation-starter. To start a conversation afterward, you can say, "Hey wasn't that scene where the main character made her decision really interesting? Why do you think she did that?"It's not what you say; it's how you say it. Talking about the movie will lead to conversations you would not have had otherwise.
Make a regular lunch date with your teen. Try to take your teenager out to lunch at least once a month with no agenda whatsoever. You're not taking them out of school and having lunch because you've got this big thing you need to talk about; don't do it in order to grill them about doing drugs or something like that. And don't do it expecting some aha moment to happen. Just take them out -you're making a deposit in a goodwill account. Later, they might talk to you instead of keeping everything deep down inside and then acting it out.
Show your child how to deal with difficulty.Teenagers especially need role model. Show your child what it's like to deal with conflict effectively. Show your teen how to handle it when you make a mistake. Apologize when you screw up or say the wrong things. Actively demonstrate good ways to deal with anxiety or stress. All of these things need to be modelled for them as much as possible.
Try to speak your teen's language. Children have become much more comfortable communicating via email and text message. It's not because they haven't developed their social skills-rather, for a teenager, texting is an important social skill. So send your child a text message once a day and say, "Hey, have a good day," or "Thinking about you" or "Good luck on your test." That way, you're reaching out to your child on their turf. It goes a long way toward building rapport.
If you find yourself struggling with these tips, then perhaps it's time you confronted your gremlin. What is she telling you about teenagers?