How to Really Listen

The Problem With How We Communicate

Recently, I was talking to a client whose boss set up a meeting to discuss a certain project. Unclear about why the meeting was called, my client jumped into frantic preparations to ensure he could show the progress he was making on this project. He was ready to defend himself.

Have you been in a situation like this before? So often, we enter conversations from a defensive perspective when power dynamics, egos, and a lack of trust are at play. Our minds race with questions: Why are they asking me this? What have I done wrong? Are they competing with me? How am I going to impress them? What can I say next that sounds smart? Insecurity rears its ugly head and sabotages our ability to be present and responsive. In this reactionary mode, we are not engaged with anyone except for ourselves. We are not listening.

As a result, the other person doesn’t feel heard and will continue on their own train of thought, further expanding the gap in understanding and connection. In these kinds of interactions, we are essentially talking to ourselves. We leave feeling empty, threatened, and disconnected.

What if I told you there’s an easier, less stressful, more effective way to approach challenging and stressful conversations? I posed this alternate strategy to my client: become genuinely curious – become a question box vs. an answer box. To do this, you must listen deeply.

Approaching a conversation with questions and curiosity (rather than defenses and answers to potential questions) leads to clarity, progress, and trust. By encouraging the other person to share more information, you can tailor your response and provide data and insight that is relevant to them. In shifting your focus away from your own agenda, you create an expansion of possibility, and this propels you both towards a common agenda. This is the result of deep listening.

The Power of Deep Listening 

Deep listening is a core element of all successful relationships, interactions, and business success. Over the past year, I’ve been researching effective sales strategies and have developed the following premise: deep listening leads to transformational conversations, which are the building blocks of real relationships and loyalty for long-term, recurring business.

By noticing below-the-surface nuances in someone’s communication, you can go even deeper with your inquiry and get at root problems, needs, and desires of the person you’re talking to. Deep listening puts you in an active vs. passive role and incorporates many senses. It goes beyond words exchanged. 

Consider these five components of deep listening in your next conversation: 

  1. LISTEN: At the most tangible level, pay attention to the words that people choose. Then, go beyond the words — what is the tone of their voice telling you? What can you gather from their inflection, pace, and pause? 

  2. BE CURIOUS: Ask questions and clarify any points you’re unsure about. Reflect back what the other person has said, and confirm you have it right. “Why?” and “Tell me more” are great ways to keep going deeper. 

  3. SLOW DOWN: Whenever there’s a pause or silence in a conversation, we’re often inclined to jump in and fill it. Resist this urge, and allow space for the organic next statement to emerge. Make space for the other person and yourself to further explain, complete thoughts, and bring formed ideas forward.  

  4. WATCH: Pay attention to the physical presence of the person you’re talking to. What is their body language telling you? Are they making eye contact? Are they uncomfortable or confident? Energized or bored? Respond appropriately to the energy they are putting forward.

  5. FEEL: What feeling do you get from the words and physical presence of this person? At the deepest level, where are they coming from? What do they want to get out of this conversation? 

Really hearing what someone is trying to convey — both consciously and unconsciously — is a fine art. You can gain knowledge from every level of deep listening. The more you pay attention, the more you will notice. And when you are in the moment and truly present, you can hear even more. 

But First, Center Yourself

Deep listening requires intentionality. For me, this means taking a minute to remind myself to be present before I enter a conversation, whether it’s with the mail person, the barista, my husband, a friend, a client, or someone I’m selling my services to. My goal is to be a receiver of information first, seeking to understand the other person so that I can respond in a way that builds rapport and trust. 

Before you go into an important conversation, check in with your own capability to listen and receive. Are you distracted or overwhelmed by something else you have going on? Do what you need to take care of so that you can enter the interaction ready to connect. That could look like jotting down a list of what’s on your mind, or postponing your conversation to a later time when you’ll be able to be present. Being proactive in this way ensures you will avoid conversations that will leave others feeling empty.

Relationships, Transformed

What do you feel like when someone is genuinely curious about you and acknowledges what you say? For me, being heard is very grounding, healing, and builds confidence. To be present and to deeply listen to someone is a profound gift. It’s what fills a human being up — we’re wired for this type of connection. Deep listening is the building block of any real relationship, and it leaves both parties wanting to come back and interact more.

Resources to Explore: 

Video: “Seek first to understand” by Mr Smart


Kristine Steinberg is the CEO of Kismet. She believes that your life should be deeply fulfilling — not tolerated. Partner with Kismet to dismantle fear, define your path, and lead with courage. Start your transformation today.

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