Think of the best conversations you've ever had—the ones that left you:
- feeling closer to someone,
- seeing something differently, or
- thinking about something you'd never considered before.
Now think of all the conversations that feel like a waste of time.
What Makes the Difference?
We often think the difference comes down to who we're speaking to, or what we're talking about. But there's another factor we rarely consider, even though it creates what’s possible for the conversation:
How we listen.
Most of us think of listening as a single activity. But there are different ways to listen, each offering something different. And becoming aware of them might be the key to having more of the conversations we value.
1. Listening to Respond
Imagine a friend tells you they've just lost their job.
Before they've finished explaining what happened, you've already thought of a similar experience you want to share, some advice you could offer, or what you'd have done differently in their situation.
Of course, conversations require responses. There's nothing inherently wrong with wanting to contribute. But there's a difference between waiting for our turn to speak and allowing what someone says to shape what we contribute.
The problem arises when our eagerness to respond gets in the way of our opportunity to understand.
2. Listening to Know
For your friend who’s lost their job, rather than immediately offering advice, you might ask what happened, whether they saw it coming, or what they're planning to do next.
You're curious. You're asking questions. You're gathering information that you didn't have before.
But what if your friend isn’t ready to figure it all out, and simply wants to feel understood?
3. Listening to Empathise
Your friend explains that losing their job has shaken their confidence. They're worried about money, embarrassed to tell their family, or struggling with the loss of a role that gave them a sense of purpose.
Now, understanding what happened is less important than understanding how they're experiencing it.
Rather than immediately seeking more information or offering solutions, you might instead focus on simply making them feel understood.
In their work on active listening, psychologists Carl Rogers and Richard Farson emphasised that listening well requires more than techniques—it requires genuine respect for the person speaking and a willingness to understand their perspective.1
This creates the shift from “What can I discover from this person?” to “What is it like to be this person?”
4. Listening to Learn
As the conversation continues, your friend reflects on how much of their identity had become tied to their career. Perhaps they explain that losing their job has made them question what success really means to them. And something they say makes you reconsider your own relationship with work, ambition, or fulfilment.
Rather than simply trying to understand their experience, you're allowing their perspective to influence your own. This requires something more than curiosity—it requires:
Intellectual humility: the willingness to acknowledge that someone else might understand something we don't, and the openness to reconsider what we already believe.
But beyond learning something from each other, what if your conversation surfaces new insights that neither of you had before?
5. Listening to Discover
Your friend admits that although they're worried about finding another job, they weren't actually happy in their previous job.
You share something you read on the difference between being good at something and finding it fulfilling. They build on it, explaining that financial security matters to them, but status matters less than they once thought.
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Then, a new possibility emerges: their next job doesn't need to satisfy every ambition. They could pursue financial stability while finding other ways to cultivate the parts of themselves that their career had neglected.
MIT Researcher Otto Scharmer calls this generative listening, the deepest of his Four Levels of Listening, in which openness and attention create space for new insights to emerge.2
This might explain why some conversations feel so extraordinary. We leave with more than information, understanding, or even a changed perspective. We leave with an insight that didn't exist for either of us when the conversation began.
Bonus—Listening Beyond Words
The way someone speaks, their facial expressions, or their posture can offer clues about their experience. Your friend might insist they're fine, despite sounding subdued. Equally, they might speak with enthusiasm about a job opportunity while appearing hesitant whenever they discuss actually pursuing it.
These observations aren't definitive evidence of what someone is feeling. But they can invite us to become more curious and ask a question we otherwise wouldn't have considered. However, it’s important to check your interpretation rather than assuming you've correctly read someone—for example:
“You say you're excited, but I noticed you hesitated a little. Are you having mixed feelings about it?”
The Real Skill Isn't Always Listening at the Highest Level
The real skill is recognising what a conversation requires and adapting accordingly:
- Sometimes, we need to exchange information (listening to know).
- Sometimes, your friend simply wants to feel understood (listening to empathise).
- Sometimes, we listen to change the way we think (listening to learn).
- And occasionally, we have the opportunity to discover something together that neither of us had considered before (listening to discover).
When we're unaware of the different ways we can listen, we risk listening without intention—failing to deliver on what the conversation is calling for.
Listening Well Doesn't Necessarily Mean Asking More Questions
Listening well could mean allowing a moment of silence, reflecting back what you've heard, or checking whether you've understood someone correctly. Rather than immediately asking another question, we might instead say:
"It sounds like that's been really difficult for you."
Sometimes, the most valuable thing we can contribute to a conversation isn't another thought of our own, but evidence that we've understood someone else's.
Equally, Being a Good Listener Doesn't Mean Speaking Less
Being a good listener means making your contributions more informed by what you've heard.
The problem isn't contributing—it's being so preoccupied with what we want to contribute that we fail to properly consider what the other person is saying.
How the Best Conversations Are Made
Great conversations are something we create by becoming more intentional about how we listen.
Listening and speaking aren’t opposing activities where one person is talking and the other is listening. Instead, it’s a form of collaborative thinking where:
- One person introduces an idea.
- The other listens, considers it, and offers a perspective shaped by what the first person has said.
- The first person then revises or develops their thinking.
- Together, they arrive somewhere neither would have reached independently.
The best listeners aren't the people who have the best thoughts to respond with. They're the people who make it possible for the conversation to lead somewhere where the two people speaking hadn't yet realised themselves.
The next time you speak with someone, don’t just ask yourself what you should say.
Ask yourself what the conversation needs—and where it might lead if you listened differently.
