By Sandy Weissinger
Most of us call it listening. It’s really just waiting to talk.
I was reminded of that recently over lunch with a new colleague. She spent most of our time sharing what’s been weighing on her, challenges with her aging parents and the uncertainty that comes with it. I mostly listened and asked a few questions to better understand.
As we were leaving, she said something that stayed with me:
“I feel like I’ve gotten to know you so well.”
That caught me off guard. I hadn’t shared much at all.
It stuck with me.
People don’t feel connected to us because of what we say. They feel connected because they feel heard and understood.
And that doesn’t happen by accident.
It comes from being fully present and willing to go a level deeper.
Where Most Conversations Fall Short
Most of us think we’re good listeners.
We’re present.
We’re respectful.
We don’t interrupt.
But often, we stop there. We hear the words, but we don’t always take the extra step to understand what’s behind them. And that’s where we miss what actually matters.
The Small Shift That Makes a Big Difference
The conversations that build trust tend to have one thing in common:
A willingness to go a little deeper.
Not with more talking but with better questions.
The second question.
Sometimes the third.
Not to probe for the sake of it but to understand more fully.
Research highlighted by the Harvard Business Review suggests that people who ask thoughtful follow-up questions are often seen as more engaged and more effective in conversations.
Not because they say more. Because they take the time to understand more.
One Important Note
This only works when it’s genuine.
Questions asked out of obligation can feel forced. Questions asked out of real curiosity tend to open the conversation.
You don’t need perfect wording. You just need to care enough to want to understand.
What This Can Sound Like
Someone says:
“It’s been a challenging rollout.”
It’s easy to move quickly to advice or solutions.
But sometimes it’s more helpful to pause and ask:
- “What’s been most challenging about it?”
- “Can you say a little more about what’s been happening?”
- “What’s been most frustrating?”
It’s a small shift but it often changes the depth of the conversation.
Why It Matters
This isn’t just about being a better conversationalist. It’s about understanding the full picture so we’re not reacting to just a piece of it.
When we take the time to ask and truly listen:
We slow things down.
We gain better clarity.
We respond more thoughtfully.
And people notice.
Not because of what we said. But because of how they felt.
Heard.
Understood.
Taken seriously.
That’s what builds trust over time and across any relationship.
3 Ways to Make It a Habit
You don’t need a script. Just a bit more intention.
- Assume there’s more beneath the surface
- “Can you say more about that?”
- “What’s behind that?”
- Stay with what stands out
- “You mentioned timing has been tight, what’s been driving that?”
- Let curiosity guide you. Instead of thinking about what to say next, ask:
- Do I really understand this yet?
The Bottom Line
Listening is expected.
Taking the extra step to truly understand, that’s where the difference is.
Because the people who stand out aren’t the ones with the fastest answers.
They’re the ones who take the time to understand the full picture. They are driven by genuine curiosity, one real question at a time.
And in the end, people may not remember exactly what you said.
But they will remember how you made them feel.
