Why Asking Better Questions Can Uncover Your Child’s Hidden Pressures

Let’s be honest. As parents, we often think we know our kids inside out.

But as they hit their late teens, a whole new world of complexities and pressures opens up for them, and we might be missing the boat. We tend to focus on the external only. Grades, activities, obvious milestones, and forget that the real treasure, the hidden gems of their character, thoughts, and struggles, lies beneath the surface.

Asking better questions are the key to this and why I devoted a section to better questions in my new book, Puddle Jumpers (Please pre-order here.) *Your pre-orders make a huge difference so thank you.

I recently experienced this firsthand with my 19-year-old son on a father-son trip to New York.

We were having a special dinner at ZZ’s, and I wanted to open up a deeper conversation below the typical surface-level topics we sometimes default to as parents.

Want better answers? Ask better questions. It’s that simple.

Erase these from your question bank: “How was your day?” or “What did you learn in school?”

As our mains showed up I asked him two questions that filled up our entire evening of conversation.

1. What’s something you’ve spent a lot of time on latelyt, a friendship, a hobby, or even a goal, and you’re starting to realize it’s just not giving you a good return on your investment?

My son paused. He looked at me, a flicker in his eyes. Then, he started talking. He said, “Probably too many parties at school.”

He spoke about the peer pressure to fit in, to go along with the crowd, even when he knew it wasn’t the best path for him. It was raw, honest, and incredibly revealing.

It wasn’t just about partying; it was about peer pressure, social dynamics, and the constant struggle to define oneself in a world full of noise and expectations on campus.

This opened the door to a truly meaningful and constructive discussion.

We talked about the importance of true friendship, about surrounding yourself with people who lift you up and support your growth. We talked about having the courage to walk away from things that no longer serve you, even when it’s difficult.

2. “Is there anything in your daily life, any pressure or challenge you face, that you think your mom and I don’t see?'“ He hesitated for a moment. Then, he looked me dead in the eye and said, “The pressure of being the son of a Navy SEAL.

“They compare me to you, and it’s a lot of pressure.”

I was floored. I had no idea that my success, my public persona, could be such a burden for him. I felt a pang of guilt, but also a profound sense of gratitude that he felt comfortable enough to share this with me.

We talked long into the night, about how proud I am of him, not because he’s my son, but because of who he is as an individual. We talked about ignoring the noise of many adults who often put their insecurities on others. And about finding his own path and defining his own success.

These simple questions, asked with genuine curiosity and without judgment, allowed me to connect with my son on a deeper level.

They helped me uncover hidden facets of his character, understand his inner world, and build a stronger, more authentic relationship.

So, I encourage all parents out there: don’t settle for surface conversations. Ask better questions. Deep dive into your children’s thoughts and feelings. Be prepared to be surprised, perhaps even a little unnerved. But I promise you, the reward is worth every bit of it.

One more thing — I’m hosting a FREE workshop on March 14th that I think you’ll want to be at. It’s called Your Voice Becomes Their Voice: The Mental Skills That Shape Strong, Joyful Kids. And in 90 minutes, I’ll walk you through the mental management tools I used to train Navy SEAL snipers — adapted for real family life.

You’ll leave with practical tools you can use with your kids ASAP, specific language shifts that build confidence instead of fear, and a framework for helping your kids handle setbacks without falling apart. Best part? It’s virtual and free with a replay available for those who can’t join us live.

Register now: https://brandontylerwebb.com/parenting-workshop