How to Listen and Build Deeper Connections with People

We’ve never had more excuses to not listen. As technology advances and content explodes, we continue to spread our attention across multiple screens, problems, and people — often all at once. As a result, attention has become one of the scarcest resources — and one of the most valuable. People who can truly listen have a unique edge in a world fragmented by distraction. They deal not just with stimulus but with engagement, not just with interaction but with connection. As Simone Weil writes, “Attention is the rarest and purest form of generosity.”

By listening, of course, we’re not talking about “hearing” people or even tracking what they mean. Listening goes beyond comprehension. To listen is to be fully present to what someone else is saying, to process their words without distraction, and to seek to understand them before trying to be understood ourselves. Listening is the currency of rapport, and the window into trust, connection, and mutual engagement. The quality of our conversations, our relationships, and our reputations all hinge on how well we can do this one simple activity.

So here’s our handy guide on how to listen.

1. Practice active listening.

“Are you even listening to me?”

The question catches you off guard. Of course you were listening, you say. Yet the other person felt the need to ask the question.

People can tell whether you’re listening by your verbal responses and your body language. When you make eye contact and nod as they’re speaking, you send a different message than if you were staring into space.

The words you use and your body language are part of a larger skillset called active listening, a process in which the listener responds to the speaker by actively processing, re-stating and responding to what they’ve heard. Active listening is crucial to communication and relationships. In order to get someone interested in you, you have to be interested in them.

The most obvious form of active listening is responding. For example, you already know you have to acknowledge someone’s thoughts to indicate you’ve been listening. But one word responses, like “yeah,” “cool,” “interesting,” or “totally,” only telegraph that you’re probably not listening. They’re not substantive statements. People catch on quickly. Think back to your last conversation like this, and you know the effect these perfunctory words have on a relationship.

The formula for a great conversation driven by active listening is simple, and it revolves around listening:

  1. Ask an open-ended question.
  2. Listen to the response.
  3. Follow up with a statement (ideally an open-ended statement — but not another question).

It’s totally fine if your questions sound random. Think back to the basics: Who? What? When? Where? Why? How? These are all great ways to start conversations. For example, if you’re talking about travel and there’s a lull in the conversation, you might just ask a random question. That might seem weird or unnatural, but you’ll be surprised at how ordinary it actually is. Conversations are hardly ever linear. (This isn’t a lecture!)

2. Connect on an emotional level.

A lot of people listen on a logical level (men, especially). Look, that’s the most straightforward way to guide a conversation, and it’s frequently the safest. So it’s not unnatural.

However, if you want to really connect with someone, you’ll have to listen to them on an emotional level. Go beyond connecting concepts and ideas, and delve into the feelings behind those concepts and ideas. For example, if your friend is an entrepreneur telling you about the time she pitched her company to investors and you’ve never started a company before, you can think back to a time you felt a similar level of pressure and anxiety in a high-stakes situation.

This is crucial in developing meaningful relationships. When you listen to someone emotionally, you show empathy. When you empathize, you recognize that someone else is as real as you. Empathy is one of the most endearing and resonating emotional connections you can have with someone else. Yet from a young age, many people are explicitly taught, or inadvertently learn, to avoid or hide their emotions.

Throughout the years (or decades), a lot of men lose touch with their emotions. Men pay less attention to their own emotions, and so they naturally pay less attention to other people’s emotions as well. They find it difficult to empathize. Their relationships have no depth or closeness because they don’t have emotional connections.

That’s okay. It doesn’t have to be like that. Here’s how you get back in touch with your emotions and empathize with the other people:

Behind everything someone says to you, whether they’re facts or opinions, there’s an emotion tied to it. Logical connections are about finding commonalities and interests. Emotional connections are not. And that’s great, because the one ultimate thing that connects all of us is emotions. Each of us may have gone through different things, but we’ve all felt the same emotions.

In order to build an emotional connection, share moments in your life where you’ve felt the same emotions. Learn about people’s personal narratives: their past (e.g., embarrassing moments or lessons learned), present (e.g., beliefs), and future (e.g., hopes, dreams, or fears).

Because personal narratives are so meaningful, most people don’t willingly open up about them to everyone. You might have to make the first move.

It’ll be uncomfortable. If you don’t talk about your past, present, or future much, you probably realize that the people in your life aren’t willing to share this stuff either. It’s challenging to build relationships and emotional connections without first being a bit vulnerable and sharing your personal narrative first. Show your emotions, elicit their emotions, and then connect the two.

When I teach in our Residential bootcamp, I will tell the story of my father passing away and my girlfriend breaking up with him. The worst part: both these things happened within eight months of each other. After that, I ask the guys I am coaching to pick one emotion from this story that resonated with them and share a story of their own based on that emotion. Half of the guys start off with, “My relationship with my dad…” or something related to, “My dad…”

See what happened there?

The men went straight for the logical connection point about fathers. It wasn’t necessarily an emotional one, though. What about sadness, grief, loss? Perhaps gratitude, or regret, or guilt? It’s important to tap into the emotions coming through.

Tapping into your feelings and relating emotionally with other people takes a bit of practice. Don’t worry if you struggle at first, because it will come with time. Best of all, you’ll notice your friendships and relationships going deeper and becoming richer.

3. Focus on the other person with questions.

“What do I say now?”

Maybe one of you just accidently touched on a sore subject, or the conversation just dried up. Maybe the other person just went to the bathroom and came back. Or maybe you feel the need to impress this person, because you realize they’re becoming more important to you. Either way, lulls in conversations can make you trip over your own two feet. Here’s how you can avoid that:

When you worry about the “right” thing to say, you’re not listening. If you were, your brain would be focused on what the other person was saying. So every time you start worrying about what to say next, that’s a helpful reminder to reinvest in the conversation.

If you’ve ever been on the receiving end of that in a conversation, you’ll realize how irritating — and obvious — it is. When you catch yourself doing that, just ask yourself questions instead.

For example, you can ask yourself:

  • What is this person saying?
  • How does this person feel about what they’re talking about?
  • What have I done that’s similar to what they’re talking about?
  • When did I feel like this?

Asking questions will prevent a common mistake, which is focusing on yourself instead of other people. It sets the stage for you to form an emotional connection with someone (more on this in a sec).

Remember always, their story should take greater priority over your story. Questions prevent you from talking about yourself. It might sound simple and straightforward, but the next time you catch yourself worrying about a lull or making a good first impression, ask yourself questions so you prompt yourself to listen. Think about, and feel, what the other person said.

4. Pay attention to how they’re saying it.

You might have already seen stats showing that the majority of our communication is done without words (estimates vary from 60% to 90%).

Since this is the case, listening means paying attention to how someone says something. You listen to their pauses, their tone, their diction, and you look at their body language and how it shifts. This whole pictures will give you insight to their emotions and what they really mean. That’s why email and instant messages can be so confusing, and why you need to be fully present when you’re listening to someone.

Develop your sensitivity to changes in their speech and body language. Look into how they express themselves:

  • Is the other person’s voice getting higher pitched? Maybe the topic makes them nervous or brings up an unpleasant memory.
  • Are they speaking faster, or stuttering more? You might have stumbled on something they’re passionate about, and so much to say their mouth can’t keep up.
  • Are they avoiding eye contact? You might have broached an uncomfortable topic.

If you naturally tend to mirror the other person, how does your body language make you feel? It won’t be easy at first, but as you pay more attention and get feedback on whether you were accurate or not, you’ll be able to more accurately pinpoint how exactly someone feels when they’re talking.

You can also use quiet moments and pauses to get more clues into how someone is feeling. If they’re interested in continuing a conversation with you, their natural reaction will be to ask a question and get to know you better. If they’re not, well, the quiet might last longer than you’d be comfortable with.

5. Use humor sparingly.

We’ve all seen the rom coms or heard social or dating advice where it’s best to make someone else laugh. There’s no denying it: laughter is reassuring, and making someone else laugh feels great.

The hard truth is: humor doesn’t make you memorable. Humor is just seasoning. It shouldn’t be a main ingredient in the recipe of your conversation.

A lot of people try too hard to be funny. They force humor when it’s not there. Yet humor breaks the emotional tension that’s building. Although you might find tension awkward and uncomfortable, it can be equally powerful if you use it correctly. As our podcast guest Oren Klaff says, “Tension is what holds people’s attention.” When you break tension, you make deeper, emotional conversations more difficult.

For example, you might be humorous when the other person is trying to talk about something that means a lot to them. They’ll feel like you’re not taking them seriously or being real with them. You didn’t mean to communicate that, but that’s what it makes them feel like. Sometimes, it’s a defense mechanism on your end, to avoid the emotional connection and to avoid getting hurt.

In the more serious or tense moments of a conversation, resist the impulse to constantly joke around. Listen. Don’t try to cheer them up or break the tension, which can be uncomfortable. Instead, listen to the words and tonality, and remember how you’ve felt the way they felt.

Closing Thoughts

Dig beyond listening comprehension and logical connections. Build an emotional connection so you can empathize with the other person and get an idea of how they’re feeling.

Don’t drive yourself nuts about what you’re going to say. Instead, bring your mind back to the moment that’s unfolding in front of you with questions. Pay attention to their, and your, body language. Pay attention and let the serious, tense, or awkward moments in a conversation happen. Sometimes, the uncomfortable or intense parts of a conversation can be the most beautiful.

You might not quite get it the first or second time you listen. Keep at it. You’ll get the hang of it. And you’ll realize how rewarding it can be.