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Engaging Teens in Meaningful Conversation

This article is meant to give you tools to engage in conversations that will help our youth explore their thoughts and emotions, and in the process, be able to gain a sense of calm, of security, and of understanding of themselves and others.

Be Curious: When we open ourselves up to being curious about our teens we can learn about them, about their thought processes, their values, their feelings, their challenges - and it is so much easier than needing to have all of the answers! Specific ways to use curiosity to open conversations include:

  • Use Open Ended Questions: Ask questions that give room for exploration, such as “what questions do you have about what is happening?” rather than “are you worried?” which requires a short yes/no response and does not allow for the teen to explore options.

  • Ask Powerful Questions: Powerful questions are the type of questions that get to the heart of the matter in a few words. They often allow us to see the big picture, gain clarity, and cut through minutia. Some examples of powerful questions are:

  • What really matters here?

  • What advice would you give to a friend in this situation?

  • In 5 years what do you want to remember about this?

  • If you weren’t afraid, what would you do?

  • What is the opportunity here?

Being curious doesn’t mean using questions to manipulate your child down a path that you think they should go down. That would be called “leading” – and our teens are way too smart to be fooled by that. Part of being curious involves us being truly open to discovery, it has a light energy and can be playful. If you find yourself feeling like a lawyer questioning a witness, or if you are asking questions that you already have an answer to in your head, then you are more than likely using questions to lead your teen. When you catch yourself doing this, change course by asking a question that you do not have an answer to and that explores your teen more and the topic less.

Reframe Their Perspective: Often when teens are struggling with something they are looking at it from a narrow perspective and making that perspective bigger in value than it actually is. One time my son, a 7th grader at the time, was experiencing great anxiety about giving a speech. In talking with him, I helped him see various ways of looking at the situation, taking the emphasis away of it being a win/lose scenario. When we were playing around with the perspective of: “what would our dog Kip do in a situation like this?” my son was able to get playful on the topic and laugh over his dog spinning his tail like a helicopter propeller with excitement to have so many people paying attention to him. For some reason, unpredicted and unknown to me, that was the perspective that switched my son’s mind from being in a state of paralysis to openness – and – one that allowed him to actually enjoy the experience of participating in the oration contest the next day.

As seen in the TED Talk here, helping your teen realize that they can choose perspectives to view their world from is a great form of empowerment, not only for the situation at hand, but for a lifetime.

In the experiential workshops that Volare offers, we work with teens to gain empowering perspectives that propel them into meaningful action in their lives. It consistently inspires us to see how powerful a perspective can be in a person’s life. To learn more about our workshops visit:

Give them think-time: Absence of the spoken word gives time for people to process their thoughts, their emotions, and come up with realizations. that can lead to meaningful choices. In our fast paced world, we rarely make room for think-time, even though it is essential to decision making. Make disciplined attempts to create space for thinking during your conversations with your teen. Model this think-time in casual conversations so they can see how you apply think-time yourself. Intentionally say “take a moment to think about this” or “let’s take a moment to reflect on this before we say anything else”. When thoughts/possibilities emerge from this think-time, play with the ideas before jumping to analysis. Sometimes our first thought may be the beginning of a strand of creative ideas that lead to wonderful insights and they need a receptive and nurturing environment to develop – even if they sound unreasonable at first.

Use Empathy: Empathy – truly feeling for another person’s experience with compassion and respect - gives us a greater appreciation of that person and communicates clearly that we care about them in a powerful way. Simple statements such as “I really see that you put a lot of effort into that and I can imagine that you are disappointed that it didn’t go the way you had hoped” speak a message of honoring their experiences and feelings. It allows the person to feel seen and valued just as they are. This is a key need of all individuals, and teens particularly benefit from this during this critical stage of developing their own identity, self-awareness, and confidence.

When expressing empathy, let it be enough on its own. I will never forget the time that I blew a huge opportunity to strengthen the bond I had with my son by using empathy as a pathway to teach him a lesson. He was playing lacrosse and made a mistake of talking back to his coach in the heat of a moment. As a result, the coach pulled his jersey and took him out of the game – the final game of the season. My son was devastated, and so was I. I wanted to make sure my son learned from this experience that he needs to control his temper. I began a conversation by empathizing with him, telling him that I really felt bad for what happened, that he was a dedicated player and team member and that having his jersey taken away on the final game must have been very difficult for him. I saw in his face that he was beginning to open up to the many emotions of the experience. There was tremendous potential in that moment. Then I blew it. I moved into a lesson on controlling his temper. I had not gotten a full sentence out of my mouth when I saw the impact I was having on him. He completely shut down and stopped listening. The empathy that I had shown him was interpreted as a set-up to navigate the conversation I wanted to have with him. If I hadn’t had such a need to “parent” by drilling a lesson in my son’s head, my son likely would have opened up and shared what the experience was like from his perspective. Through that sharing he likely would have drawn his own learning, which would have likely been more meaningful than the predictable speech I was trying to give him.

Since then I have made it a priority to put myself in my son’s shoes and imagine what different experiences might be like for him. I have vocally expressed empathy for his experiences, as well as respect and admiration for his efforts – with no hidden motivations. This simple act has allowed our relationship to deepen and our appreciation for one another to grow. The bottom line: sincere empathy matters, even to teenage boys.

Be OK with emotion: Emotions are a natural part of being human, especially being a teenager. Consider the surge of hormones, daily incidents with friends and romantic interests, and the stress of academic workload – your teen is going to be experiencing a LOT of emotions in a day, maybe even in a single minute.

It is important to let our teens know that emotions are a part of life and that expressing them in healthy ways is essential to well-being. Emotions do not make us weak, they make us human. Avoiding or neglecting our emotions results in them interfering with our ability to live fully and have a negative impact on our health. Teaching our teens how to release their emotions in healthy ways is essential to their overall well-being. Further exploration of how to do this will be addressed in Part Three of this series.

We want to be good parents and educators. We want to give our children every support possible as they develop into young adults. Guiding them with our wisdom and our life’s experiences is best received when given in balance with opportunities for our teens to discover and decide for themselves.

I realize that it can be difficult resisting the need to take care of our teens and keep them safely on the well-trodden path to security and success. Part Two of this series: Connecting with your Teen’s Character and Strengths – gives strategies to support you give teens the space that they need to authentically develop a strong sense of self and become the creators of their own lives with confidence and assurance.

Coming Soon:

Part 2: Connecting with Your Teen’s Character and Strengths

Part 3: Teen Emotions Are Not the Enemy - You Can Handle Them!

About the Author: Regina Hellinger is director of Volare, a nonprofit organization dedicated to connecting teens to their passion and purpose. She is a professional coach and educator with an extensive background in character education and gifted education, providing coaching and consulting for families and professional development for educators. For questions, more information, or to receive future articles, email Regina at

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