1. “What’s been on your mind lately?”

This opens things up without putting anyone on the spot. It’s not demanding or intrusive. It invites someone to share what’s occupying their mental space right now.

Most people are thinking about something meaningful—work stress, a family situation, an idea they’re excited about. We rarely give them permission to talk about it. This question does.

2. “What would help right now?”

When someone’s going through something difficult, we often jump to advice or sympathy. Neither is wrong, but sometimes what people actually need is to be asked directly what would be useful.

Maybe it’s listening. Maybe it’s distraction. Maybe it’s practical help. This question recognizes that you don’t assume to know—you’re asking them to tell you.

3. “How are you really doing?”

The emphasis on “really” changes everything. It signals you’re not looking for the polite answer. You’re interested in the truth, whatever that might be.

It gives permission to be honest, even if that honesty is uncomfortable. Research shows that authentic self-disclosure strengthens relationships. Someone has to create the opening first.

4. “What’s something you’re proud of that you don’t talk about much?”

We’re conditioned to downplay our accomplishments. This question flips that script and invites people to celebrate themselves without feeling boastful.

It shows you see them as more than their problems or struggles. You’re curious about their wins too, even the quiet ones.

5. “What’s been harder than you expected?”

This acknowledges reality without forcing vulnerability. It normalizes struggle without making it the center of attention.

People often feel pressure to have it all together. This question gently suggests that you understand things aren’t always easy, and that’s okay.

6. “What’s changed for you recently?”

Change is constant, but we don’t always have language for it. This question invites reflection on shifts—big or small—that might be shaping someone’s experience right now.

It’s open enough that people can take it anywhere. New perspectives, new routines, new realizations. Whatever feels significant becomes the answer.

7. “What do you need more of in your life?”

This is forward-looking without being prescriptive. It doesn’t assume someone is broken and needs fixing. It simply invites them to identify what’s missing.

Maybe it’s rest. Maybe it’s adventure. Maybe it’s boundaries. Whatever it is, naming it out loud is often the first step toward getting it.

8. “What’s something you’ve been wanting to say?”

Sometimes people are carrying thoughts they haven’t found the right moment to express. This question creates that moment.

It shows you’re listening not just to what’s being said, but to what might be waiting beneath the surface. That kind of attention is rare.

9. “What’s making sense to you right now?”

Life is messy and often confusing. But there are usually small pieces that click into place, even during chaotic times.

This question invites someone to share their clarity, however modest. It shifts focus from what’s overwhelming to what’s becoming clearer. That shift alone can be incredibly grounding.

Final thoughts

These questions aren’t magic formulas. They’re starting points. What makes them powerful isn’t the exact wording—it’s the intention behind them.

When you ask questions that invite depth rather than demand it, you create space for real connection. You signal that you’re interested in more than the highlights reel. You’re interested in the person, with all their complexity.

And that’s what being truly seen feels like. Someone asking the kind of question that assumes you have something worth sharing, then actually listening to the answer.