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10 Questions To Strike Up Meaningful Conversations With Your Teen

Updated: Jul 1, 2022

Everyday our kids are forming opinions of the world around them and how they fit in it. Ultimately, how they see the world will determine what they are motivated to do. It is incredibly important that, as parents, we take the initiative to shape that perspective. While this seems like something any reasonable parent would do, the demands of everyday life can cause even those with the noblest of intentions to fall short. Fortunately, building perspective does not take an extreme amount of time or effort. One simple way to do this is by having meaningful conversations with our children. The following are 10 "non-awkward" questions that you can ask your teenager to incite reflection and dialogue.

Questions adapted from book, 80 Questions for Adolescents: A Guide to Making Sense of School and Life


1. In your opinion, what does having a successful life look like?

Parent Notes:

This is an opportunity to have a meaningful conversation with your child about success.  You may want to look up the definition of success and discuss it with them. Since success should look different for each individual, listen for misconceptions that your child may have about success.  Be encouraging but also use this time to provide perspective.


2. Where do you think your idea of success comes from?

Parent Notes:

Help your child understand that we are all being influenced by something or someone, even when we are not aware of it.  Encourage them to trace the source of why they feel the way they do about success.  Where necessary, help them objectively understand the pros and cons of their concepts of success (e.g. What will they have to sacrifice? What are the statistics?).


3. What are you currently doing to achieve success?

Parent Notes:

Does your child understand what it takes to be successful? Challenge them to express specific actions that they are doing to support their idea of success.  Make sure they are looking at practical indicators such as school performance, choice of friends, and time wasters.  Be prepared for them to get a little defensive.  In response, use real life examples to help them think more objectively.


4. How would you describe your self-esteem on a scale of 1 - 10 (10 being the best)?  Explain.

Parent Notes:

It is easy to assume that your child’s emotional well-being is fine. Yet, that may not be the case. Make sure that your child understands that self-esteem describes how they feel about themselves.  Encourage them to express how they truly feel.  If they need help opening up, describe insecurities you may have had in the past (or even what you may be dealing with in the present).  You may find an emotional connection point that may open an opportunity for growth in your relationship.


5. What are your top 3 career interests right now?  Why?

Parent Notes:

One of the best ways to learn about your child is to ask them what they want to do.  They may answer you with something that you would have never imagined.  All answers will give insight. For instance, even the answer “I don’t know” lets you know that their inner senses may need to be stimulated through new experiences (or questions like these). 

Ideally, their answers should have a logical connection in some way to their answers in the first 3 questions.  If not, then use this as a moment to help them understand that their choice of career should reflect their ideas of success.  For instance, a child that has stated that a major success factor is “to do something they are passionate about” should have at least one career choice that they are actually passionate about.  Share your input but let them know that you value their capacity for building the future they want.


6. How do your talents support your career interests?

Parent Notes:

While we all have the ability to dream, there comes a time where some of those dreams must meet reality.  The question we all must ask ourselves is do we have the talent to actually do what we say we are going to do?  Your child is not exempt. In fact, it is best that they start their journey to truth early.  Listen carefully to what your child believes their talents are—you may learn a lot about them.  Then, as necessary, share what you have observed about their talents and the attributes that you think make them great.  Be encouraging.


7. What are the biggest personal challenges that you will have to overcome to pursue those careers?

Parent Notes:

Help your child understand what it takes to achieve their career of choice. Do the research. Challenge them to research.  If your child has the talent, the next question is are they willing to take the necessary steps?  Many people don’t ever get to show off their talents because they fail to develop the necessary skills to get their foot in the door.  

Challenge your child to be candid about their fears.  Does he or she desire to be a speaker but avoids the stage? Do they say they want to be an engineer but hate math?  Help them to be honest with themselves and think deeply about what it is they truly want.  Then guide them towards the actions that align with that.


8. What are the positive and negative influences you have identified in your community?

Parent Notes:

Ask them how they feel about their neighborhood and school.  Many young people feel “trapped” mentally long before they commit actions that negatively affect their lives.  Challenge them to identify negative and positive influences and reinforce the reality that most outcomes are a reflection of choices made.  Guide the conversation to help them develop a more sound perspective of their environment and the situations they put themselves in.


9. Do you believe that you can make a positive impact on your community? Why or why not?

Parent Notes:

It is important for kids to believe that they can make an impact. So many of them grow up thinking that they are only a product of their environment and, subsequently, end up being victims instead of victors.  Why do they (or don’t they) believe that they can make an impact?  Look for fundamental ideals that may be shaping what they believe.  Encourage them by letting them know that they are leading someone—that is, someone is looking up to them as a role model.  Take note and make a plan to cultivate their belief in the right ways.


10. What goals can you set right now to move you in the “right” direction?

Parent Notes:

After having conversations about the questions listed above, students should be ready to turn their ideas into something concrete. Have them get a pen and paper and get to work.  Help them to articulate what they have identified as their interests, bad habits, and good attributes.  Make sure they understand what a goal is. Help them make a list of things that they can begin doing to help them achieve the life they desire. 

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