Three kinds of listening
There is listening to win an argument.
There is listening to fix a problem.
And there is listening to actually understand.
Most senior leaders have spent decades becoming extraordinarily good at the first two. The third is the one that changes rooms. And almost nobody has been taught how to do it — because it is not, in the usual sense, a skill.
The first kind
Listening to win an argument is not always aggressive. Often it is subtle, even courteous. You let the other person speak. You nod. You wait for the pause. And while you wait, you are not hearing them — you are preparing your response. You are looking for the flaw in their reasoning, the opening in their position, the moment you can re-enter and redirect.
This kind of listening is indispensable in negotiation, in boardrooms, in any context where positions must be defended. There is nothing wrong with it, except that it has a cost: the person across from you can feel it. They may not be able to name what they are sensing, but they feel the absence of genuine curiosity, and they respond in kind. The conversation becomes a transaction. Both sides leave having exchanged information, and neither has learned anything.
The second kind
Listening to fix a problem is warmer, and it is where most good leaders live. Someone comes to you with a difficulty. You listen carefully. You begin to pattern-match: this is like the situation last quarter, or this is a stakeholder alignment issue, or this is a confidence problem. And almost immediately — often before they have finished speaking — you have a solution forming.
This is generosity. It comes from genuine care and years of competence. It is also, quietly, a way of managing your own discomfort with not knowing. As long as you are solving, you are in control. The other person gets an answer. What they do not get is the experience of being fully heard before the direction was chosen.
Over time, this kind of listening produces a particular loneliness in the people around you. They come to you with their problems and leave with your solutions. They stop bringing the things that are not yet problems — the half-formed doubts, the questions they have not finished asking, the discomfort they cannot yet name. You become efficient and a little isolated, and you may not notice the connection between the two.
The third kind
The third kind of listening is different in nature, not degree. It is not a better version of the second. It operates on a different principle entirely.
When you listen to genuinely understand, you are not preparing a response. You are not diagnosing. You are not matching what you hear against what you already know. You are simply present with what is being said, including the parts of it that the speaker has not yet said — the hesitation before the sentence, the phrase that was almost chosen and then abandoned, the feeling underneath the report.
This sounds simple and it is extraordinarily difficult, because it requires you to tolerate not knowing. For a senior leader who has built a career on knowing — on being the person with the answer, the clarity, the direction — this tolerance is not a small ask. It goes against years of conditioning that say: silence is a vacuum, and vacuums are yours to fill.
Why this cannot be taught as a technique
The usual advice is: do not interrupt, ask open questions, reflect back what you hear. These are fine instructions, and they miss the point entirely. You can do all three while internally composing your next move. Technique addresses behaviour. The barrier to the third kind of listening is not behaviour — it is tolerance.
Tolerance for not fixing. Tolerance for sitting with someone else's confusion without needing to resolve it. Tolerance for hearing an idea you believe is wrong without immediately correcting it. Tolerance for the silence that arrives when someone runs out of their rehearsed version and reaches for something truer.
That silence is where the work happens. Not yours — theirs. And if you cannot tolerate it, you will fill it, and the moment will pass.
The ceiling
Here is the part that is rarely said.
You cannot listen to another person more deeply than you listen to yourself.
The container you offer someone else — the space in which they feel safe enough to think, to feel, to not know — is the one you have already built internally. If you cannot sit with your own uncertainty, you will not be able to sit with theirs. If your own discomfort with silence sends you reaching for a solution, you will reach for one in their silence too.
This is why improving your listening does not start with other people. It starts with noticing what happens inside you when the urge to fix arrives. Not suppressing it — that creates a different kind of tension, and people feel that too. Noticing it. Letting it be there without acting on it. Finding out what is on the other side of the pause.
Most people who try this discover something surprising: the discomfort passes faster than they expected, and what follows it is a quality of attention they did not know they had.
What changes when you listen differently
When someone is truly heard — not advised, not diagnosed, not redirected, but heard — they begin to hear themselves. They slow down. They stop performing the version of the problem they arrived with and start discovering the version they have not yet articulated. They surprise themselves.
This is not a soft skill. In a negotiation, it is the difference between a deal and an impasse. In a leadership meeting, it is the difference between compliance and commitment. In a difficult conversation, it is the difference between the same argument again and something actually shifting.
And in the quiet moments — the ones that matter most and are spoken about least — it is the difference between being around people and being with them.
One thing to notice
This is not an exercise. There is no checklist at the end of this piece, because a checklist would put you back into the second kind of listening — the kind that reaches for a tool.
Instead, one invitation.
Think of the last conversation you had today — any conversation. Notice which of the three kinds you were doing. Not which you wish you had been doing. Which you actually were.
That noticing, without judgement, is exactly how the third kind begins.
Kunal Gupta is an executive coach working with senior leaders across 19 countries. Start a conversation or read why he does this work.