It’s not surprising that when you look at the description for each of the generations — like Baby Boomers, Gen X, and the Millenials, known as Gen Y and Gen Z — that I tend to think more like a Millenial than my own generation. That’s because I was immersed in their world for nearly two decades, as I lived at a boarding school where my husband was a teacher. Through that experience, I was able to walk with them through disappointments and failures as well as through triumphs and the precious moments of success.
It only made me want to be more skilled at connecting with them, as I knew that beyond their tough exterior were hearts crying out for soul deep love.
So when I embarked on life coach training, it was really for the sake of gaining a skill-set to use in my informal role as mentor to teens. I had no idea that God planned to use it in entirely different way.
Apart from time spent steeped in the Word and going to counseling for whole-heart healing, the training I experienced in becoming a life coach has literally become the greatest investment into my development as a mom.
Through learning how to ask open-ended, thought-provoking questions, while actively listening to the heart, I’ve been able connect on a deeper level with my own growing up next generation children. Whether it is sitting at the kitchen counter with my college-bound teenage daughter or interacting with my tween-agers and their peers, learning how to ask the right kind of question at the right time has transformed my ability to really get into their thinking and help them process life through an eternal perspective.
It’s always amazing to me how the right kinds questions, asked at the appropriate time, can open the doorway to a teen’s heart and establish a meaningful connection.
So how about I share with you a sneak-peek of what I’ve learned and how you can apply it in your relationship with your tweens and teens?
Step One: Consider Your Overflow
How often do we focus all our energy on helping our kids, while forgetting that the best thing we can do for them is take care of ourselves? We can’t serve them authentically from the overflow of Christ within us, without being whole and healthy spiritually and emotionally. So before you set off on a mission to connect, consider the state of your heart, mind and soul.
- Do I need to reprioritize my life to make time to spend with God and in His word daily?
- Do I need to make an appointment with a counselor to address a wound or struggle that is impacting how I’m engaging with my tween/teen?
- Do I need to ask for forgiveness from God and my tween/teen for anything that might be an obstacle in drawing closer to them?Is it time for me to get involved in a Bible study, either at church or with a few women, to be held accountability to grow in my faith and dig deep in the word?
- Am I at an emotionally healthy place and ready to take the next step to grow personally? Consider this option or this one.
Step Two: Consider the Moment
Before launching into a conversation that is meant to connect with your teen’s heart, consider the moment and how to set the stage for a sweet, tender time together.
- Are they too tired for the conversation?
- Who is in earshot that might keep them from talking?
- What’s on their mind that might be a distraction — or maybe a more pressing need to chat about?
- Is there an offense or hurt between the two of you that needs to be reconciled?
- Do you need to, seek help from a godly friend, a pastor, or counselor to figure out what needs to happen to restore an emotionally and spiritually healthy connection with your teen before you can engage with them on a regular basis?
- Is there time to have this conversation without being rushed?
- Is there a good time to plan for this conversation, such as a long car ride together or going out for dinner?
- Have you spent time praying about connecting with their heart?
Step Three: Ask a Question
These five questions are just enough to get you going in the direction of connecting with the your teen’s heart, but be sure to NOT ask all of them at once or they will feel like they are on the firing squad. Pick one question and leave it at that — and remember, you’re job isn’t to come up with the answer or solution. You simply want them to open up and share, without being criticized, advised, or being turned into a project.
- What’s the most challenging thing happening in your life right now?
- What are you most afraid of as you think about the next season (in life, academically, or athletically) ahead of you?
- If you could change one thing in yourself, what would it be?
- If you could change one thing about our family or your friends, what would it be?
- What are you most grateful for or happy about?
BONUS QUESTIONS
If the conversation is going well, you can pick one of these bonus questions to ask as a way to go deeper:
- Would you like my help in brainstorm a solution?
- Would you like my advice?
- Could I share my experience?
- How could I pray for you?
- Would you like to talk about this again in the future?
If you’d like more questions like these, check out the 21 Questions resource from More to Be.
Step Four: Plan a Follow Up
Once you start connecting with your teen’s heart, there’s no need to stop. Make a plan, with the Lord, to follow up with your teen again. Consider their willingness and the moment, as you make a plan for talking together. If they would like to follow up, the conversation could start with picking up where you left off. If that wasn’t the direction, you could start fresh with another question.
As a woman who thinks like a Millennial, I can promise you this: Your teens want to talk with you, and more importantly, they want to connect in authentic way with a woman like you.
They want to hear your stories, know your struggles, and feel your support, even if what you see is a standoffish behavior and too much eye-rolling. I pray you’ll risk your pride and step out in faith to connect with your teens on a real heart-to-heart level.


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