What If You Stopped Asking “How Was Your Day?
A few days ago, I was scrolling through LinkedIn and paused at a post from another entrepreneur. She shared how much she dreads the question, “So… how’s business going?” Not because business is bad, but because the question itself feels flat, limiting, and unable to hold the truth of her experience.
It reminded me just how powerful questions are—and how much they shape what we’re able (or willing) to share. As a coach, I’m trained to ask the kinds of questions that invite depth, honesty, and connection. But even outside the coaching space, the right question can open a door.
Years ago, I read an article about a couple who discovered this firsthand. He worked outside the home; she worked inside the home, caring for their young children all day. Every evening they exchanged the familiar, “How was your day?” And every day, his answer overflowed with client anecdotes, triumphant wins and new developments… while hers felt like a highlight reel of diapers, spit-up, and the constant giving that motherhood requires.
Eventually, they realized that the question itself wasn’t serving them. So they changed it.
Instead of “How was your day?” they asked things like:
What was the best part of your day?
What challenged you today?
What brought you joy?
What did you learn about yourself today?
Suddenly the conversation shifted—from reporting to reflecting, from routine to connection, from monotony to meaning. All because they asked a better question.
Questions are portals. They can deepen intimacy, spark laughter, dissolve distance, and reveal parts of ourselves we didn’t even know were waiting to be revealed.
This week, I invite you to practice asking better questions—with your partner, your friends, your work colleagues and your children.
Here are a few more questions to play with:
What did you create, imagine, or dream about today?
What energized you—and what drained you?
Where did you feel most like yourself this week?
What’s something you’re looking forward to?
What support would feel good for you right now?
Try asking one or two of these each day. Notice what opens up.
How might asking these kinds of questions transform your relationships?
“Questions are portals. They can deepen intimacy, spark laughter, dissolve distance, and reveal parts of ourselves we didn’t even know were waiting to be revealed.”