Listen Like You Mean It: Reclaiming the Lost Art of True Connection

by Ximena Vengoechea

Most of us listen well enough, but without deliberate attention we may move through conversation with significant blind spots. It’s easy for us to learn only part of the story, or misunderstand it entirely. Miscommunication can escalate a neutral situation to a negative one, and make an already negative scenario worse.

Too often, we “solve” for miscommunication by focusing only on what we say and how we’re saying it: if we could only get our message across, things would be much easier. As a result, we may decide to adjust our messaging or dial up the volume. But when we focus solely on our capabilities as speakers, we risk turning our conversation partners into an audience rather than equal collaborators. It will be hard for others to relate to us, much less put their trust in us, if that happens.

Every conversation is an opportunity to understand and connect with others much more deeply, if we know how to listen.

In many ways, empathy is the antidote to projecting—we do not need to share in others’ direct experience, we just need to imagine it. We can call upon our own experiences as a way to understand what others may be going through, but always keep the focus on the other person. Finding ways to personally relate—without making the conversation about us—allows us to better understand what is being said, not just at the surface level but also at the emotional level.

To put empathy into practice, try these tips: Let others’ perspectives take the lead. Embrace the process of understanding your conversation partner’s lived experience by asking questions specific to them and giving them the floor to share more. Remind yourself that it’s not about you. If you find your mind wandering to, “I would have handled that differently . . .” do your best to table these thoughts. Think less about how you would have reacted if it were you and more about why your conversation partner may have made the choices he or she did. Tap into their emotions. Even if you do not have firsthand experience with your conversation partner’s exact experience, try to relate to the underlying feelings that may be driving the conversation. With empathy as our starting point, we can begin to meet others where they are in conversation.

Below are a few tips to shift your mindset to one of humility. Let go of preconceived notions. Loosen your grip on your opinions to make room for others to share their own. This allows you to hear things as they are or could be, rather than as you assume they are or wish them to be. Leave judgment at the door. Remind yourself that a difference of opinion is simply that—not better or worse, just different. This can help you stop yourself from shutting others down when they feel differently. Assume you are in the presence of an expert. Understand that others’ lived experience gives them unique expertise. This can help us to accept and respect their perspective, even when it is not like our own.

Getting curious means being open to learning more about a topic, idea, or person—even if it does not initially pique our interest.

“Being interested is more important in cultivating a relationship and maintaining a relationship than being interesting,” Kashdan says. “That’s what gets the dialogue going.”

Try to channel that feeling where everything is shiny, interesting, and new to you, even when it feels like a stretch. To do this, find your “in”—a thread or detail you are naturally drawn to—and seize it by asking questions like, “What was that like?,” “How did you learn that?,” or “Tell me more about this part of what you said . . .” to help you go down the rabbit hole of curiosity together.

By remaining curious even when we have a strong baseline of knowledge, we can deepen our expertise and in turn better get to know others. If you are well versed in a topic, don’t stop there. Instead, ask yourself: What details might I be missing? What else can I learn? How might my understanding of this subject be incomplete?

What can a person’s choice of topic tell you about them? Getting curious about why this person is so drawn to this topic helps us silence our old friend, projection. The following thought starters can help: How important does this subject seem to my conversation partner? Which part of our conversation are they particularly passionate about? Not passionate about? What might be driving their [enthusiasm, frustration, disappointment] for this topic? Could there be an emotional, contextual, personal, or even historical reason for their choice of topic? What might be motivating their reaction to what’s been said? Might their personal history play a part?

There are three skills that allow us to stay present as we listen, each of which builds upon the other and requires mindfulness, the ability to be aware of what is happening in a given moment. Self-Awareness helps us know what each of us personally needs to stay present so that we can be there for others in conversation. Trust allows us to stay in the moment and receive others with ease rather than worry we will forget something important or miss our conversation partner’s point. Patience helps us to slow down our response and make space for others to finish their thoughts or take their time to process or sit with what’s been said.

If, despite your best intentions to orchestrate the right conditions, you find yourself unable to stay present and be the empathetic listener your conversation partner deserves, postponing your conversation may be your best bet. The most effective way to do this is to be honest: share why you’d like to table your chat and offer an alternative. For instance, you might say: I want to make sure I’m operating at 100% for our chat. Let’s talk in the morning, when I’m likely to be freshest. Discussing this is important to me, but I can feel myself fading fast. I need a snack and then I’ll be able to focus. Mind moving this conversation to a café with me? I’ve learned that too many social outings leave me zapped, and I’ve already had three today. OK if we meet tomorrow instead? Some solo time will help me recharge for our conversation. I want to give this the attention it deserves, but I am so freaking tired. Can I call you after I nap?

When you are desperate to weigh in, consider what information you might miss by doing so. Take a time-out and simply wait. Count to ten and see what you can learn by staying present and observing. If this feels impossible, I find that creating a physical restriction like sitting on your hands, wriggling in your seat, or even giving yourself a teeny, tiny pinch if need be can also help pass the time as you pause.

NONVERBAL GESTURES AND THEIR COMMON MEANINGS Zone Gesture Emotion Window into the Soul Eye contact Connection, confidence, focus Smiling Happy, cooperative, polite Frowning Sadness, confusion, worry Self-Regulating Neck touching Insecurity, distress, discomfort Hand on collarbone Concern, shock, stress Nail biting Boredom, unease, anxiety Clenched fists Frustration, anger, restraint Fidgety fingers, hand-wringing Nervousness, distress, worry Engagement Feet pointed away Ready to leave, disinterested Feet pointed toward Committed, interested Alliance Leaning toward Comfort, agreement Crossed arms Defensiveness, insecurity Open arms Receptive, eager, warm “Large” postures (outstretched arms and legs) Territorial, dominance “Small” postures (crossed arms and legs, hunched shoulders) Unease, lack of confidence

BROAD STATEMENTS Phrases like “I like it,” “it’s good,” “sure,” and “whatever” are often signals that there is more to be said. They are usually employed when people are afraid of offering their honest opinion for fear of appearing controversial, hurting someone’s feelings, or not being appropriately invested in the topic at hand. When you hear broad statements like these, you can gently follow up to get more clarity, remembering that your conversation partner’s choice of words already speaks volumes. Depending on the relationship, it may be more productive to carefully coax out your conversation partner’s honest opinion, or to call them out directly to be more specific. Choose accordingly and say something like: Help me understand what you mean by . . . What do you [like, dislike] about . . . ? Tell me how you really feel.

The phrases below can help you reach the heart of the matter when apologetic and flattering language is getting in the way: I value your perspective on this. Please don’t hold back. Your honest opinion means a lot to me. What else comes to mind? I always learn so much from your ideas. I’d love to hear more. Your input is invaluable. Tell me how this is landing.

If a stalling or bolstering phrase crosses your path, take note. Depending on the relationship, your approach may vary. When trust exists between you and your conversation partner, you may want to encourage your conversation partner to be more forthcoming. Try the following phrases: I’m sensing some [hesitation, avoidance, uncertainty, etc.]. Be honest with me about how you are feeling. It seems like we are dancing around this topic. How do you really feel about it? It feels as if there may be more to be said on this one. Tell me about your current thinking. I sense you may be holding back. What’s really on your mind? For less intimate relationships, this type of encouragement can sound invasive, or even accusatory. Instead, you can gently give your conversation partner the space to find their words. Here, offering a warm smile and a bit of patience can help them share more on their own terms. We can all empathize with feeling rushed, nervous, confused, or protective about what we want to say next.

In the presence of displacement phrases, try these responses to keep the conversation going and dig deeper into the underlying emotion. Remember to tread carefully, since the closer you get to the underlying emotion, the more tender it may be. I’m wondering if we are still talking about [the dirty dishes, the unmet deadline, who paid the bill last, etc.]. Is there something more going on? I’m noticing our conversation is escalating; is . . . still the problem, or is this about something else? I think I may have upset you, but I’m not sure if it’s about . . . anymore. I can see talking about this is important to you; help me understand your reaction.

Below are the most common default listening modes, each with its own strengths and weaknesses. As you enter in conversation, listen for when these modes are surfacing, and with whom. The Explainer. Explainers have an answer for everything, especially when it comes to our feelings (You’re feeling burned out? It must be because of our culture of overworking.). Rational thinking can provide welcome perspective and help us gain distance from our feelings. Still, Explainers must catch themselves not to go overboard, since we don’t always want an explanation for our emotions; that type of response can come across as short-sighted and dismissive. The Validator. It can feel great to talk to a Validator, especially when you are in need of a pick-me-up (Yeah, it is their fault! They don’t understand you!). These natural cheerleaders are always on our side, but unchecked, Validators can unintentionally inflate your ego, skew your perspective, and even stunt your personal growth. The Identifier. Identifying happens when a listener likens their experience to the speaker’s and brings a conversation back to them. “I know exactly what you mean.” “I felt the same way when . . .” “It’s like how when I . . .” These responses can help us to feel less alone in our experience. At the same time, not everyone craves affirmation; in these cases, identifying responses can be disconnecting. They show the listener that we aren’t listening at all—we’re thinking about ourselves. The Problem-Solver. Pro...

LISTEN FOR HIDDEN NEEDS Cue Meaning I wish that . . . If only I could . . . If I had things my way . . . If it were up to me, I’d . . . In an ideal world . . . Desire, opportunity, lack, shortcoming I’m swamped I’m exhausted I’m running out of steam I haven’t gotten as much done as I would have liked to today Plea for help I miss . . . I’ve been thinking about when . . . It’s been a while since . . . Nostalgia I’m working as hard as I can I’m going out of my way here I’m doing the best I can Plea for recognition I never know what to do when . . . I can’t figure out . . . I’m at a loss . . . Need for direction

Try, for instance, the following: This seems important. What would be most useful at this moment? Would hearing [a different perspective, some advice, a similar experience] help? I have some ideas, but I want to make sure I know what you’re looking for. Would it be welcome to share [my perspective, advice, etc.]? Would it be useful if . . . ? Would you like me to listen or respond?

The questions below provide a starting point for reflection without overwhelming our conversation partner. Are you looking for something action-packed or low-key? Would you call this feedback a must-have or a nice-to-have? Would you say you feel more frustrated or disappointed? Is it more about wanting a raise or wanting to be recognized?

Incorporate new information. If we cling to existing knowledge—of our conversation partner’s feelings, intentions, mood, or point of view—without making way for new understanding, we may be perceived as stubborn, out of touch, inflexible, or even ignorant. Give others a chance to surprise and inform your thinking in conversation. Make the necessary space to receive new information: show your conversation partner you are listening through nonverbals like eye contact and nodding, and by expressing affirmations (Yes, go on.). Pay attention to your conversation partner’s behavior—verbal and nonverbal—and incorporate these cues as you determine your response. Reassess as you go. Given the information you’re taking in, is your current “script” still the right one, or is a pivot appropriate? Gut check whether your next set of questions or even responses remain relevant given what you have learned already. Keep questions and ideas on hand to further the conversation, but be open to exploration, too. Look for cues that you are heading in the right direction. As you loosen your script, continue to monitor your conversation partner’s response. Are they receptive, or do they seem to be lost, distracted, or even frustrated? This, too, should inform your approach, and where the conversation goes next.

But silence, if you can sit with it, can be very powerful in conversation. Silence opens the space between us. Silence can indicate: You have the floor. Do with it what you will. Take the time you need to. I am here when you are ready to say more.

SYNTHESIZE WHAT YOU ARE HEARING Phrase Theme That changed everything . . . That’s when I realized . . . Turning point or milestone Earlier I felt that . . . I used to believe . . . I now understand . . . Progression Building off of what you said . . . Adding to that . . . Consensus If things were different, I would . . . If I had it my way . . . Compromise, yearning I’m not sure I agree that . . . It’s hard for me to see it that way given that . . . The argument doesn’t hold since . . . Disagreement I can plan to . . . Can you confirm you will . . . It’s decided that . . . As a next step, let’s . . . Commitment

GIVE A HEADLINE SUMMARY Playing back what we have heard may sound easy enough in theory, but how do we know exactly what to highlight in the moment? Aim for a headline summary or bullet point recap—the TL;DR or executive summary version of what you’ve heard. Keep things short and sweet (e.g., a sentence) to make it easier for your conversation partner to quickly weigh in on whether you’ve gotten it right. Think like a beginner and use simple terms everyone can understand as you summarize to ensure terminology doesn’t obscure the crux of the issue. For example, instead of saying, “So, your manager is putting too much work on your plate, and you’re doing a lot of projects at once this month,” play it back, like, “It sounds like you’re struggling to balance your workload.” Or, rather than say, “Your roommate is emotionally needy and getting on your nerves, your sister won’t stop calling, and your boss is a nightmare who turns to you for key projects but never gives credit where credit is due,” give a high-level recap and say, “It seems like you are in high demand—and under a lot of stress.”

Below are a few phrases you can use to play back what you’ve heard, and invite others to correct you as needed: It sounds like . . . is that a fair reading? You mentioned that . . . Did I get that right? Tell me if I’ve understood correctly . . . What I think I’m hearing is . . . Does that capture it? This seems important, and I want to make sure I’m getting it right . .

The following questions can help you solidify your understanding and get back on track: Does that answer your question? Have I understood correctly? Is that what you were looking for? Does that seem like an accurate recap?

To escape from drowning in a sea of ambiguity, try the following phrases: What do you mean by that? I’m not sure I follow. I’m wondering if that means . . . I think I’m missing something. Can you break it down for me? Help me to understand your thinking. Do you mean that . . . Help me understand how you are feeling. Is it that . . . My understanding is . . . Please correct me if I’m wrong.

But if push comes to shove, a follow-up note may be the only way to confirm your comprehension. If we run out of time to play back what we’ve heard or have only limited access to our conversation partner, the written word can help. If you go this route, keep things short and to the point: a simple “Recapping what I think I heard earlier, it sounds like . . .” will do. In a note to her director, my friend outlined what she had heard and proposed next steps given their chat, adding, “Can you confirm if I’ve got it right?” That made it very easy for the director to quickly respond and reassure her that there was no formal ask behind their conversation, but that she had made a great sounding board.

Redirecting serves two main purposes: it makes someone aware of where they are in conversation (whether they are spinning on a topic or going off track, dominating the conversation or about to put their foot in their mouth), and it protects both your and your conversation partner’s time and energy.

Here are a few phrases you can use to coax your conversation partner toward what’s really on their mind: You mentioned you wanted to talk about . . . I know you’ve been thinking about . . . Should we talk about that now? There was something else you wanted to discuss . . . I’m remembering there’s something in particular you wanted to cover. Should we tackle that?

Simply reminding your conversation partner of how much time you have left together (or how much time you’ve spent on a possibly irrelevant topic) can be enough to help them see where they need to direct their attention. Try, for instance: It’s getting late; should we chat about . . . ? The [café closes, train arrives, meeting ends] in thirty minutes; let’s cover . . . first. I want to be mindful of your time; let’s talk through . . . now. We’re halfway through our time together—should we prioritize talking about . . . ?

The phrases below can be used to redirect the conversation and help your partner see their problem spot: It seems like this is important to keep thinking through. It sounds like it might help to dig in here. I get the sense you are still working on this. It feels like this might need more thought. I want to go back to something you said earlier. You mentioned something that really stuck with me.

Use the following phrases to reframe the situation and encourage a fresh perspective in conversation: What happens if we think about it from this angle? What if we assume the reverse to be true? What if we take this as a given? What if we assume that’s up for grabs? What if we imagine all options are on the table? What if we change our time frame?

The following redirecting phrases can bring equilibrium to the group. These work by acknowledging one party’s input before inviting others to contribute—this way no one feels dismissed or ignored, and everyone feels heard. Thank you for that detail and context. What else do people think? I appreciate the input. How does that resonate with everyone else? Recapping X’s experience, it sounds like . . . What are others’ experiences like? That’s a [fair point, good idea, reasonable request, etc.]. Thoughts from the other side of the table? Thank you for sharing how you feel. Let’s bring the rest of the group in now.

The next time you find yourself working hard to keep the conversation from wandering, try these on for size. Let’s concentrate on what we were talking about earlier. How about we return to the goal at hand? Let’s remember what we wanted to discuss. Why don’t we come back to that? Outside the office, many of our conversations come with agendas, even if we don’t call them that, as we saw in chapter 6. For instance, if you’re catching up with an old friend and are overdue for a life update, the “agenda” may be to jam a year’s worth of milestones into one dinner. If the conversation strays and your friend starts to recount everyone’s personal news but her own, and you’re eager to hear how she’s been, you can reiterate the “agenda” to get back on track with a few well-placed phrases: Catch me up on that [new promotion, engagement story, work milestone, etc.]. Remind me about [how you’re settling into that new job, what the latest is on the home front, etc.]. Let’s go back to that [life update] you were going to share. Talk to me about [how you’ve been feeling, how the family is, etc.].

When you have determined that a topic is worthy of more discussion, or, on the contrary, that we’ve said all we need to say, the following phrases can help. They work by being explicit about our intent and our proposed direction. These phrases create space to delve deeper into a topic: I think it’s worth spending more time here. I want to go back to something you said earlier. You mentioned something that piqued my interest. Let’s give this some more thought. These phrases keep things moving along: I want to switch gears for a minute . . . I’m also hoping to talk about . . . Let’s make sure we also cover . . . I want to make sure we get to catch up on . .

In the heat of the moment, our conversation partners may not be ready to walk away from their quarrel. When a dispute is on the verge of becoming an all-out brawl, we can use the promise of future resolution to redirect. Each of the phrases below acknowledges our interlocutors’ tender spot and gently steers the conversation toward new ground, with a suggestion to return to the subject as needed: I understand you feel strongly about this subject. Since not everyone here can relate, maybe we can return to this with a smaller crowd later. Would that be OK? I can see you have a lot to say on the topic. If it’s all right with you, let’s come back to this after we finish [celebrating, toasting, etc.]. Your passion for [sleep training, etc.] is palpable, but perhaps we can continue that discussion after dinner. Are you open to that?

The following redirecting phrases can be used without revealing your motivation: That reminds me of . . . How interesting. In other news . . . Speaking of . . . Have you heard about . . . ? I’ve been meaning to update you on . . .

In some cases, it may be necessary to be explicit about why you are redirecting. If we are comfortable with our conversation partner or if we do not fear reprimand, it can be more productive to let them know why we are redirecting, especially if our conversation partner has crossed a moral or ethical line, or overstepped a boundary. Try, for instance: I’m not comfortable with where this conversation is going. Let’s look at . . . instead. This conversation is getting out of hand, and I feel compelled to step in. I recommend we shift to . . . instead. This is totally unprofessional and uncalled for. A better subject would be . . . It seems like we are getting ourselves unnecessarily riled up. Why don’t we talk about . . . instead.

Asking for a time-out works best in conversations with those with whom you already have a certain amount of intimacy and can actually strengthen your connection. By being honest with our conversation partner, we show that we trust they will understand where we are coming from; we show the same honesty and vulnerability we hope they’ll share with us, too. Consider, for instance, the following phrases: I hate to do this, but I think I need to stop. I am exhausted and having a hard time focusing. This conversation is important to me, but I’m having trouble hearing you at the moment. I think I need a breather—I’m noticing how charged this is for me. I can tell this conversation is getting the best of me. I need a time-out. When possible, we can also give others a heads-up on when we will be ready to return to the topic. I want to make sure I get this right and need some time to think through it. Can we pick this back up tomorrow? I need a bit more time to make sure I’ve understood your position fully. Mind if we come back to this in an hour? I think I know what you mean, but I’m not 100% certain how I feel about it. Can we keep talking about this next week?

Diversions work by suggesting you can no longer talk because a competing priority or activity requires your attention. These phrases are designed to make the reason a conversation has to end more about you than the other person. They can be specific (I need to go walk my dog.) or vague (I have to get going now.), but generally, the less specific the better. Keep it courteous and to the point. Here are a few examples: I have to get going now, but it was good to see you. I won’t take up more of your time now; I’d better go. I’d love to talk some more, but I’m really late. I’m sure you’re very busy, so I’ll let you go now.

To effectively interject, we must get over our discomfort, call it like it is, and admit we are interrupting. Consider the following phrases: I’m so sorry to interrupt, but I have a meeting I need to get to. I’m sorry to have to hit pause here, but I really have to get going. Pardon the interruption, but we really must take off now. Excuse me for interrupting, but I don’t feel comfortable discussing this right now. Apologies, but I have to stop you there—I’m not ready to address this at the moment.

You can help your conversation partner warm up to discussing a taboo topic with a few simple steps: Tell them in advance what you’d like to talk about. This gives everyone a chance to mentally prepare in advance and ensures no one feels blindsided by a taboo topic. You’d appreciate the same courtesy, too. Clarify your intent. The best way to prevent the conversation from being automatically shut down is to clarify your rationale for bringing up these unwieldy issues. If a topic feels off-limits, you can make it safe for others to participate by explaining why you are broaching the subject, and by reassuring them that your goal is not to offend or push too hard. Simply stating what your intent is up front can reduce some of the fear around taboo topics. In my conversation with Rita, I let her know that things might get uncomfortable, but that my intent was not to provoke her. Start small and build from there. When it’s time to talk, start from neutral ground to put everyone at ease. There’s typically at least one thing you can safely agree on before your views diverge. (A manager sharing critical feedback with a direct report can admit, “I had trouble with this when I was in your role, too.”) This can build confidence to tackle the harder stuff.

The next time you’re faced with a difficult conversation where values are on the line, try the following: Affirm, affirm, affirm. Show your conversation partner that you are listening and are interested in what they have to say, even if you don’t agree with it. Encourage them to say more in a way that feels authentic to you, whether nonverbally (maintaining eye contact, nodding), verbally (OK, go on), or both. If you are known to heavily sigh, roll your eyes, or shut down at opinions that don’t align with yours, do your best to curb those habits. You can support your conversation partner and affirm their existence, even if your perspectives differ. Explain without convincing. When it comes time for you to share your perspective, do so humbly and without an agenda—the goal is not to convince others that you are right. Try not to get too bogged down in specifics that can be hard for others to connect to, but share instead what informs your perspective. For example, do you support sustainable efforts because you grew up in the countryside and have fond memories of being in nature with your parents? Talk about that instead of diving into the minutiae of the Paris Climate Agreement. Remember, it’s not about you. Part of what can make taboo topics like politics and religion so divisive is that they hit against our belief systems. To encounter an opposing point of view can sometimes feel like a rejection of our entire being. Remind yourself—before, during, and after the conversat...

Difficult conversations happen when external stimuli (certain settings, people, and topics) trigger something internally (fear, anger, pride, stress, or even boredom) that must be acknowledged, tamed, or quieted in order for us to continue to listen with empathy. What sets me off may be different from what sets you off, but no one is immune. When the going gets tough, we need to work twice as hard to stay moored in conversation. In the end, empathetic listening is what can transform a difficult conversation into a moment of breakthrough, understanding, vulnerability, and greater connection.

Empathetic listening takes work, but if we’re not careful, in our attempts to take care of others we can forget to take care of ourselves. When this happens, we become tired, burned out, and no longer capable of connecting or listening with empathy. By managing our listening drain and giving ourselves opportunities to recover, we can start feeling better and connect once more. Only when we feel recharged and steady in ourselves can we truly make space for others.