the art of asking better questions

The Art of Asking Better Questions: Opening Doors to Deeper Family Conversations
Posted by Kelly

Some of the most meaningful stories live just beneath the surface—waiting for the right question to bring them to light.

We often ask our loved ones, “How was your day?” or “What’s new?”—and while those questions are kind, they rarely open the door to deeper understanding.

But ask, “What’s something you wish more people knew about you?”
And suddenly, you’re in the heart of something sacred.

At Woven Word Press, we believe that behind every person is a tapestry of untold stories—and asking better questions is the thread that brings them to life.

Why Questions Matter

Good questions do more than gather facts. They invite reflection. They build bridges. They show someone you care enough to want more than surface-level answers.

In families, asking meaningful questions creates a space for laughter, vulnerability, memory—and often, healing.

Tips for Asking Better Questions

1. Be curious, not just polite.
Ask because you truly want to understand. Let your questions be invitations, not interviews.

2. Get specific.
Instead of “What was your childhood like?” try “What was your favorite spot to go as a kid, and why?”

3. Don’t rush the answer.
Let silence work in your favor. Sometimes, the best stories take a moment to surface.

4. Follow the thread.
When someone shares a detail, lean in: “Tell me more about that,” or “How did that moment shape you?”

10 Questions to Try

Whether you’re sitting across the table or writing in your journal, here are a few questions to spark deeper connection:

– What’s a memory that always makes you smile?
– Who taught you something you’ll never forget?
– What was your hardest season—and what helped you through it?
– What did you dream of as a child?
– What’s one tradition you hope continues forever?
– What’s a mistake you made that turned out to be a gift?
– What did love look like in your family growing up?
– What’s something you’ve never shared, but always wanted to?
– Who are the people who made you, you?
– If your story had a title, what would it be?

Questions Are Legacy, Too

Every meaningful question you ask becomes part of your family’s legacy. It says: You matter. I want to know you. I want to remember.

Whether you’re using The Fabric of Me, sharing our Threads Between Us conversation cards, or simply having tea with someone you love, remember this:

You don’t need to know all the answers.
You just need to ask the right question—and listen with your heart.

With care,
Kelly Kraus
Founder, Woven Word Press