I am not a naturally good listener, but I have tried to become excellent, so I have had to rewire my natural impulses. Mostly my inborn instincts were towards babbling. So the first step, of course, was to simply talk less, and pay more attention to others. Ask a question or two, and realize that if you try to talk about 25% of the time, you will end up talking 55% of the time, which is better than the default. However, this is not sufficient.
When your approach to being a listener simply involves asking someone else questions, and pouring attention on them, there are limits to how well the conversation can go. This conversational style tends to feel like an interview, or, worse, like you’re a spy, searching for gossip or doing oppo research. You can achieve depth, but it doesn’t really feel like an alive thing, in the way that great conversations do.
I’ve found that the next step in being a good listener actually involves shifting part of my attention back towards myself. You have to monitor your own energy and that of your interlocutor. Both are vital. Even if you’re letting someone else do most of the talking, it’s still an exchange. We might imagine otherwise: simplistically, we could conceive of listening as just prompting and absorbing output. But this is limited: in actuality, listening is a read-write operation. Anyone but the most tone-deaf conversationalist will measure your reactions, and adjust themselves accordingly, determining the importance and acceptability of their words through the subtleties of how you listen.
For me, a helpful metaphor is to imagine myself as a resonant vessel, which can reflect certain frequencies, but is dead to others, depending on my mood. My job, as a listener, is partially to pay attention to how I’m resonating with what’s being said, and to reflect that resonance outwards. Perhaps most of what I’m hearing lands in me with a dull thud. But almost whoever I’m listening to, there is something that will resonate. Perhaps it’s a person’s unexpected facets emerging, or a moment of emotional fluorescence. Whatever it is, if I notice even a little flicker of energy inside me, and I respond—with a question, or even just a smile—I’ve given my dance partner the information they need to be interesting to both of us.
This is not an intellectual operation, even if the subject of the conversation is intellectual. It’s primarily a bodily kind of listening. Interest, like meaning, begins as a felt sensation. When I’m listening well, maybe 65% of my attention is resting in the words I’m hearing, and 35% is in my nervous system.
If you can listen in this way—which requires openness, sensitivity, and a looseness of agenda—you can naturally bring someone you’re talking to towards a place of mutual aliveness and excitement. On some days, I can do this, on some others, I can’t. When I can’t, the job is then to figure out what’s getting in my way. Maybe I’m too restless, and the conversation needs additional walking. Maybe I’m wrestling with an unacknowledged emotion and it’s blocking the listening channels. In that case, my job becomes either soothing myself, or giving up on being an excellent listener, and retreating to the more modest goal of not talking too much.
This sounds like how Sayadaw u Tejaniya tells his students to practice while listening. He says to keep your attention gently on your body and mind while listening, and you'll naturally follow what they're saying and also notice how your mind is receiving what's being said. It's all in his book Relax and Be Aware. I think you would dig it.
Picture that you are connecting to the person heart-to-heart, not mind-to-mind, and the resonance will be more easily sensed and communicated.