Listen Like You Mean It

Listening is not just about hearing words; it’s about understanding the meaning behind them and making others feel truly heard.

1. Listen with empathy, not assumptions

Many of us think we’re good listeners, but we often fall into the trap of surface listening. This happens when we hear someone’s words but fail to grasp their deeper meaning. Instead of truly engaging, we make assumptions or project our own experiences onto the conversation. For example, Eve, a researcher, assumed her interviewee ignored cyberbullies because others had said so. This led her to dismiss his actual feelings, creating a disconnect.

Empathetic listening requires us to focus on the other person’s emotions and experiences without inserting our own. It’s about creating a safe space where they feel understood. To do this, we need to cultivate three qualities: empathy, humility, and curiosity. Empathy allows us to imagine their feelings without making it about us. Humility reminds us we don’t have all the answers, and curiosity keeps us open to their unique perspective.

When we listen empathetically, we activate a virtuous cycle called the listening loop. This encourages both parties to share openly, deepening the connection. By asking thoughtful questions and avoiding assumptions, we can transform surface-level exchanges into meaningful conversations.

Examples

• Eve’s assumption about the interviewee’s feelings on cyberbullying led to a missed opportunity for connection.
• Asking “How do you feel about that?” instead of offering advice can open up deeper dialogue.
• Acknowledging someone’s unique experience, even if it differs from others, fosters trust.

2. Stay present by observing yourself and others

Being present in a conversation means more than just showing up physically. It requires self-awareness and attentiveness to the other person’s emotional cues. If you’re tired, hungry, or distracted, your ability to engage fully diminishes. Similarly, if your conversation partner seems disengaged, it’s important to notice and address it.

Self-awareness is the first step. If you’re not in the right headspace, be honest about it. For instance, if you’re exhausted, suggest rescheduling or changing the setting to re-energize the conversation. At the same time, pay attention to your partner’s body language, tone, and word choice. These emotional indicators often reveal more than their words.

For example, sustained eye contact might show curiosity, while avoiding it could signal discomfort. If you sense they’re holding back, gently prompt them with phrases like, “Help me understand what you mean by that.” This shows you’re invested in their perspective and encourages honesty.

Examples

• A morning person might struggle to connect with a night owl during early conversations.
• A colleague saying “I’m fine” while avoiding eye contact might need a nudge to share more.
• Noticing your own low energy and suggesting a coffee break can improve the interaction.

3. Adapt your listening style to meet their needs

Everyone has a default listening style, but it doesn’t always align with what the other person needs. Some people are explainers, offering solutions when others just want to vent. Others are identifiers, relating everything back to their own experiences. And some are interviewers, asking so many questions that the conversation feels like an interrogation.

To connect better, identify what your partner needs and adjust your approach. Listen for hidden cues in their words. For example, phrases like “If only I could…” might reveal a desire for support, while “I’m doing the best I can” could signal a need for recognition. Once you understand their needs, acknowledge them and respond accordingly.

Sometimes, all they want is for you to listen without offering advice or sharing your own stories. This can be challenging, as it feels passive. But simply being present and empathetic can be the most supportive thing you do.

Examples

• A friend venting about work might just need validation, not solutions.
• A colleague saying “I’m going out of my way here” might need acknowledgment of their effort.
• Switching from offering advice to just listening can make someone feel truly heard.

4. Use connecting questions to deepen conversations

Shallow questions lead to shallow answers. To foster meaningful dialogue, ask connecting questions that encourage open-ended responses. These questions often start with “how” or “what,” such as “How do you feel about that?” or “What would you do if…?” They invite the other person to share more and help you understand their perspective.

For example, when the author interviewed a journalist, she initially received short, unhelpful answers. By asking broader questions like “What does a good story look like?” and following up with “How do you know?” she eventually got a deeper response. Neutral framing is key—avoid questions that assume a specific answer.

After asking, summarize what you’ve heard to confirm your understanding. For instance, say, “It sounds like you’re feeling overwhelmed. Is that right?” This gives them a chance to clarify or expand, ensuring you’re truly on the same page.

Examples

• Asking “What are your thoughts on this?” instead of “Do you like it?” encourages more detail.
• Summarizing someone’s feelings and asking, “Does that sound right?” ensures clarity.
• Following up with “How would you approach this?” can lead to surprising insights.

5. Stay flexible and embrace unexpected turns

Conversations don’t always go as planned, and that’s okay. Instead of sticking rigidly to a script, adopt a “yes, and” mindset. This improv technique encourages collaboration and keeps the dialogue flowing. For example, if someone brings up an unexpected topic, build on it rather than shutting it down.

Flexibility also means being open to new information. If your partner’s feelings or perspective change, adapt your approach. Pay attention to their responses—if they seem disengaged or frustrated, adjust the conversation’s direction. Silence can also be a powerful tool. Pausing for a few seconds often prompts the other person to share more.

For instance, when the author interviewed someone about an app prototype, she used silence to encourage honesty. After repeating his words back to him, she waited quietly. Within seconds, he opened up with a more genuine response.

Examples

• Using “yes, and” to build on someone’s idea keeps the conversation dynamic.
• Noticing a partner’s frustration and shifting topics can prevent conflict.
• A well-timed pause can prompt deeper sharing.

6. Redirect conversations that go off-track

Sometimes, conversations veer away from their intended purpose. To bring them back on track, redirect politely and thoughtfully. Acknowledge the other person’s concerns, express interest in their perspective, and suggest revisiting the topic later.

For example, when the author interviewed Jordana, the conversation kept shifting to unrelated topics. By addressing Jordana’s concerns and promising to return to them, the author was able to refocus the discussion. This approach also works for avoidant behavior. If someone is dodging a difficult topic, gently remind them of the purpose of the conversation.

Redirecting isn’t about control—it’s about ensuring both parties get what they need from the exchange. By balancing empathy with assertiveness, you can guide the conversation without alienating your partner.

Examples

• Acknowledging someone’s unrelated concern and suggesting a later discussion shows respect.
• Gently reminding a colleague of the meeting’s purpose can refocus their attention.
• Balancing empathy with assertiveness helps guide the conversation effectively.

7. Understand why conversations become uncomfortable

Discomfort in conversations often stems from differences—whether cultural, gender-based, or hierarchical. For instance, New Yorkers might interrupt as a sign of engagement, while others see it as rude. Similarly, men and women may interpret “hm-hmm” differently, leading to misunderstandings.

To navigate these challenges, be mindful of potential divides. If you’re in a position of power, create a safe space for honesty. If you’re the less powerful party, remind yourself that the other person is just human. When discussing sensitive topics like politics or religion, aim for understanding rather than agreement.

Recognizing your own “hot spot” topics—those that trigger strong emotions—can also help. Have a plan to stay calm, such as repeating a soothing mantra or taking deep breaths.

Examples

• A boss encouraging honesty can make employees feel safer sharing concerns.
• Acknowledging cultural differences in conversational styles prevents miscommunication.
• Preparing for sensitive topics with calming techniques reduces emotional reactions.

8. Know when to exit conversations

Not all conversations are worth continuing. If a discussion becomes toxic or conflicts with your priorities, it’s okay to step away. Setting boundaries protects your energy and relationships. For instance, if a friend repeatedly complains without reciprocating support, it’s time to reassess the dynamic.

Time-boxing is one way to manage this. Set a time limit for the conversation upfront, or choose a location with natural time constraints. If things get heated, ask for a time-out. Phrases like “I think I need a breather” can defuse tension and create space for reflection.

Afterward, take time to recover. Empathetic listening is draining, so prioritize self-care to recharge.

Examples

• Setting a 30-minute limit for a meeting prevents it from dragging on.
• Asking for a time-out during a heated discussion allows emotions to cool.
• Scheduling recovery time after a tough conversation helps maintain balance.

9. Practice active recovery to avoid burnout

Empathetic listening takes effort, and it’s easy to feel drained if you don’t set limits. This is called listener’s drain, and it can affect your mental, emotional, and physical well-being. To avoid burnout, recognize your limits and schedule time for recovery.

Recovery looks different for everyone. It might mean reading a book, exercising, or simply sitting in silence. The key is to honor your needs and give yourself space to recharge. By taking care of yourself, you’ll be better equipped to support others.

Examples

• Taking a walk after a difficult conversation clears your mind.
• Journaling about your feelings helps process emotional exchanges.
• Setting aside quiet time each day prevents listener’s drain.

Takeaways

1. Practice empathetic listening by focusing on the other person’s emotions and avoiding assumptions.
2. Use connecting questions to encourage open-ended responses and deepen conversations.
3. Set boundaries and prioritize self-care to maintain your energy and emotional well-being.