Help Me Understand What It’s Like to Be You: The Question Every Parent Should Ask

Middle school can be a confusing and often painful time for children. Friendships shift, self-esteem fluctuates, and emotions can run high. As parents and caregivers, our instinct is to help — but sometimes, in our desire to fix things, we forget the most powerful tool we have: listening.

In a recent episode of the Bent Not Broken podcast, Licensed Professional Counselor and author Stacy Schaffer shared an insightful approach to truly connecting with children during challenging moments. Instead of assuming we know what they’re going through, she suggests we begin with a simple, compassionate question:

“Help me understand what it’s like to be you.”

This question invites openness. It tells a child, “I care about your world, not just my perspective of it.” It shifts the dynamic from parent-as-problem-solver to parent-as-partner — someone who listens, learns, and supports without judgment.

Stacy reminds us that middle school (and really, all of adolescence) is tough for almost everyone. Pretending we know their experience can create distance. But asking, “Tell me your experiences — how is that making you feel?” opens the door to trust, empathy, and emotional safety.

As adults, we often forget that the greatest gift we can give a child isn’t advice — it’s understanding. So next time your child seems withdrawn or frustrated, pause before offering solutions. Try this instead: “Help me understand what it’s like to be you.”

You might be surprised by what they share — and how much closer it brings you together.