Your teen's lack of assertiveness could have adverse consequences in many areas of his life -- he might have trouble making friends, asking the opposite sex out on dates, communicating his needs in different situations, standing up for himself during arguments or asking questions in school. As an adult, it could negatively impact his chance for career success and ability to maintain healthy relationships. You can help your teen become more assertive by teaching him how to communicate those deeper, yet vital aspects of himself.
Many teens are too intimidated to speak up and express their feelings. Their parents might have belittled them so they gave up trying, or they're just not skilled in self-expression. Letting your teen know that you value his feelings can help him feel that it's safe to talk about them. In the beginning, he might need some gentle coaxing. You might say, "How do you feel about the birth of your new sibling?" or "Are you sad that your best friend is moving to another town?" Whenever he manages to express feelings, even if the initial attempts are brief and awkward, tell him how much you appreciate that he shared them with you.
Don't Always Say 'No'
If you're constantly saying "no" to your teen, he might give up trying to assert himself because he's constantly being shot down. Instead of always saying "no," show that you respect him by learning the reason for his request. For instance, if he wants permission to stay out past his curfew, ask him why the extra time is so important, which forces him to assert himself. You might agree to a compromise -- one extra hour instead of the two hours he asked for. By remaining flexible, it shows you honor his needs and desire for autonomy. You're also teaching that self-assertion is actually a healthy way to get what he needs.
Value His Opinions
Your teenager might have such low self-esteem, he doesn't believe his opinions and ideas are valuable. To teach him that his opinions are important, ask for them whenever possible. It doesn't have to be major -- even encouraging him to voice which he'd prefer for dinner, the meatloaf or chicken cacciatore, can help your teen learn to speak up for himself. If you disagree, don't interrupt him and respect his point of view. Let him pick out the movie for a family outing, and later ask what he thought of it. Help further build his confidence by saying, "Thanks for sharing your interesting opinion. It provides a lot of food for thought."
Let HIm Speak for Himself
If your teen is so unassertive that he's slow to respond when others speak to him, resist the urge to become his spokesperson. It might be tempting to jump in and speak for your shy son during those awkward pauses, but by rescuing him, you're sending him the dangerous message that he's incapable of speaking for himself. Instead, be patient and allow him to speak, no matter how long it takes. When Grandma asks him how he's enjoying school, you might gently nudge him out of his paralysis by saying, "Tell Grandma about the "A" you received on your science project." Eventually, your teen will become more comfortable speaking for himself without your intervention.