Empathy in Action: How to Listen in Tough Conversations

INTRODUCTION

Being a good listener during tough conversations is a skill of great value, one that can transform challenging dialogues into opportunities for growth, understanding, and problem-solving. Tough conversations require a level of attentiveness and empathy that goes beyond typical everyday communication and can challenge the limits of our abilities to stay engaged productively. The ability to listen well under such circumstances is not just about hearing the words being spoken, but about fully comprehending the emotions, intentions, and underlying messages conveyed by the speaker.

The sections that follow will explore techniques that underpin good listening, including the suspension of judgment, the patience to absorb and reflect, and the discipline to avoid interrupting and jumping to conclusions. Good listeners approach these conversations with an open mind, ready to understand perspectives that may differ from their own, and willing to acknowledge the complexity of other people’s emotions and experiences.


KEY TAKEAWAYS

  • Good listening requires being clear about what is expected of you as a listener.

  • Listening is meant to enhance understanding for greater closeness, not debate.

  • Being a good listener is an active role with specific expectations, not passive disengagement.


GETTING STARTED

Why It Can Be So Hard to Listen

Conflict often sounds like this – nobody listening and everyone disagreeing. This is because conflict threatens disconnection, and the way we often try to regain that connection is to eliminate differences so that we can share a common ground.

This is the common unstated message:

“If I can just get you to see things my way, then we won’t have a problem.” 

This way of thinking lets us off the hook for really needing to listen to whatever the other person is saying. We’ve already made up our minds about what’s “right” and what needs to happen next.

This kills closeness and ultimately fuels further conflict and polarization.

The following are 10 steps for how to listen well with your loved ones during difficult conversations.


STEP 1

Prepare Yourself to Listen

Commit to yourself a willingness to be in the “listening role.”

This means that you, at this moment, are not fighting to be heard against the words of another. 

Good listeners don’t give up their perspective, but they do practice patience when hearing another person’s account of events.

Postponing your own agenda for a while creates space in the relationship for the other person to speak openly without worrying about being cutoff or needing to defend their position against yours.


STEP 2

Listen to Understand, Not to Rebut

Don’t be the person that counters or dismisses everything you disagree with.

Instead, be open to hearing a perspective that’s different from yours and show a willingness to explore those differences.

  • Get out of assuming you really know what happened.

  • Get out of judging your partner for experiencing life differently than you.

You both have different personalities and life experiences that influence how you interpret the world around you. Negotiating between these subjective realities is what builds intimacy, trust, and respect for your differences together.


STEP 3

Recognize Defensiveness

Defensiveness doesn’t care about intimacy and doesn’t care about your relationship. It’s the start of a stress response that walls you off in self-protection instead of opening you up to accepting influence.

If you’re on the receiving end of criticism, duck under the other person’s poor delivery and listen to the emotion they’re really trying to convey. 

The other person may still need to work on their communication skills, but this will help move you out of the knee-jerk response that only cares about protecting yourself and into prioritizing greater connection.


STEP 4

Ask Questions to Deepen Understanding

Being a good listener also means being a good interviewer. It shows a desire to really know the other person.

Practice asking questions like the following:

  • What was the hardest part about this situation for you?

  • What feelings do you have about this?

  • What’s the most difficult feeling?

  • Is this a familiar feeling? Does it relate to your past in some way?

  • What was that like for you?

  • Tell me more. I’m listening.

Be careful not to ask too many questions. Endless questioning, even if well-intentioned, can make the other person feel interrogated.

Avoid asking questions that cross-examine the other person’s position. Questions like “Don’t you think that if…?” send the message that you’re trying to get them to come over to your way of thinking, rather than exploring theirs.


STEP 5

Reflect Back What You Hear

Don’t assume that what you’re hearing is what the other person is trying to say. You may be hearing only what you know, or what you expect to hear.

Reflection Structure

“So you felt [emotion] about [situation] because [reasons].”

Even if you think you do get what they’re saying, the other person needs to hear themselves reflected back accurately in your words. Be open to corrections if your reflection doesn’t communicate the most important elements the other person needs to hear most from you.

Don’t judge their experience and don’t counter with how much you disagree. The goal is validation and empathy.


STEP 6

Share What Makes Sense to You

This soothes emotional reactivity in the other person.

It shows that you’re acknowledging their history, state of mind, and current events that influenced their experience without critical judgment.

Examples

  • “It makes sense to me based on what you saw (or heard) that you would feel [emotion] and think [thoughts]”

  • “Based on your past experience with [event or similar situation], I can see how this current situation would have affected you the way it did.”

  • “I may not fully understand all of it, but I do see that this really affected you and left you feeling [emotion]. What does stand out to me is what you said about [part of their experience].”

You may not understand all of it as you listen and there may only be a small part that really makes sense to you. That’s ok, but do focus on what is understandable to you.


STEP 7

Take Responsibility for Your Part

Demanding your partner to do anything is a losing strategy.

This doesn’t mean that you’re the source of the problem, but acknowledges ways in which you may play into the present difficulties.

This helps shift the exchange out of combat and into collaboration. Look for something that may call for an apology from you, then tell the other person.

Examples

  • I got defensive

  • I didn’t listen to you

  • I was stubborn

  • I attacked you

  • I wasn’t respectful

  • I was impatient

  • I was controlling

  • I was walled off

  • I was stuck in trying to be right

Commit to addressing these difficult parts of yourself that you bring into conversations with the other person. Drop the justification for your poor behavior and work on a plan for avoiding this response in the future.


STEP 8

Thank the Other Person for Sharing Their Feelings

Moving toward greater intimacy during difficult conversations requires that we take the initiative to express gratitude for sharing difficult feelings instead of responding with mere defensiveness.

Example

  • “Thank you for sharing that with me, I appreciate it. I know it couldn’t have been easy.”

In this way, we signal our commitment to the relationship and communicate openness and respect to the other person.


STEP 9

Let Them Know Their Message Will Stay with You

Even if nothing has been resolved, letting the other person know that you will keep in mind what they’ve said communicates that you’re expanding what you know about them, what triggers certain emotions, how they respond to those emotions, and why it has that effect on them.

Example

  • “It’s not easy to hear what you’re telling me, but I want you to know that I’m going to give it a lot of thought.”

This shows that you’re creating space in your mind specifically for this relationship and knowing the other person, which is needed before moving into problem-solving together.


STEP 10

Make a Constructive Plan

Your chances of reaching an effective resolution are far greater once you’ve moved toward greater understanding and respect for each other’s experiences.

Take some time to identify aspects of the issue where you may be flexible and willing to compromise. The goal is to find as many areas of flexibility as possible to work together on a compromise.

However, it’s normal to discover during this process areas where you may not be open to compromising. These areas usually speak to some part of your personality, values, dreams for the future, or belief system. Be respectful of these areas and focus on where there is more movement for change. Don’t go back into criticizing and nagging.

Examples

  • “Based on what you’ve said, here are some things I could do differently…”

  • “What are you thinking would be most helpful in being able to put this behind us?”

  • “What do you need from me?”

  • “I think it would also help me if you were to…”

Finally, make sure to check in with each other at a later date to review whether the changes you both made have been working.


Conclusion

These steps can be difficult to implement, but with practice create opportunities to understand each other better than before. By staying present, showing empathy, and maintaining an open mind, you are better prepared to connect with the emotions and intentions behind them. Next time you find yourself in a challenging conversation, employ these strategies and see how your conversations can start to change for the better.

JASON PERUCHINI, LMFT

Jason Peruchini is a licensed psychotherapist and anxiety treatment professional who helps people address issues in mental health to live better lives.


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