Last updated: November 24, 2025 

The holiday season brings people together — and it often brings tension right along with it. You may find yourself rehearsing conversations in your head or staying quiet at family gatherings because saying the wrong thing could cause a rift. That’s why I’m re-releasing this episode on how to have difficult conversations in a way that protects your relationship (and can even strengthen it) rather than pushing you further apart.

“People almost never change without first feeling understood.”

-Douglas Stone

“I don’t want to talk about it right now.” 

“It’s not going to change anything.” 

“It will just start a fight.” 

We have all, myself included, used these kinds of mental excuses to avoid having difficult conversations. We all have “trigger topic” conversations we’d rather avoid — from opening up to your partner about sex, to having different opinions on politics, having an issue with someone’s parenting styles, or gently pointing out subconscious bias in gender roles or racist stereotypes. These conversations are hard to have. If you’re struggling to approach them constructively, couples counseling can give you a supportive framework to do this well.

While there is something to be said for knowing when to mind your own business and respect the healthy boundaries of others, it’s also true that if you’re avoiding having conversations about things that are really, really important to you it will eventually damage your relationship — whether or not you address it directly.

Having unresolved, unspoken differences that feel vast, and “un-discussable” will lead to disconnection. But the sad irony is that it’s often people’s hope to protect their relationship that leads them to avoid difficult but necessary conversations in the first place. If you need support building the skills to talk through these moments, relationship coaching can be a great starting point.

How to Have Better Conversations

Crucial conversations are essential. But once you embrace the new idea, “Yes, we do actually really need to talk about this,” then what? 

Unless you’ve already gone through communication skills training, therapy, relationship coaching, or emotional intelligence coaching, you might not know how to have a difficult conversation productively. 

That lack of skills and know-how is one of the biggest reasons why most people tend to tiptoe around difficult conversations, OR — on the flip side — engage too aggressively around triggering topics, both of which can damage a relationship.  

Now, more than ever, I believe that we all need to learn and intentionally practice compassionate communication skills that can help us have empathy for each other and build bridges to the center of shared meaning. 

In this episode of the podcast, I’m shining a light on what it really takes to courageously engage in difficult (and necessary, and respectful, and healing) conversations with the people you care the most about.

Having Difficult Conversations

I hope that this episode leaves you with some actionable ideas for how to increase your confidence in high-stakes conversations, and provides you with strategies for increasing your emotional intelligence and communication skills in the process. You can use these strategies with your partner, kids, friends, family, coworkers, or anyone else you need to have a tough conversation with.

In this episode, How to Have Difficult Conversations:

• Discover how refusing to have difficult conversations damages relationships.
• Learn essential skills in having constructive and productive conversations. 
• Gain a deeper awareness of your own feelings and motivations.    
• Identify relationships where it’s worth having these conversations and those that require clearer boundaries. 
• Learn how to make these conversations more comfortable through regular relationship check-ins.
• Embrace the discomfort of having difficult conversations.
• Avoid common pitfalls and knee-jerk reactions in difficult conversations. 
• Learn to listen with compassion, respect, and empathy. 
• Find out how to reciprocate openness and willingness to exchange ideas. 

Listen right now to “How to Have Difficult Conversations” on Spotify, or on the Podcast App, or by scrolling down to the podcast player on the bottom of the page. If you’re more of a reader, you can skim through the show notes and/or find a full transcript at the bottom. 

Thanks for taking the time to listen to this episode and triple-thanks if you’re one of the courageously kind, heart-centered people in the world committed to having respectful, difficult conversations that heal. The world needs you!

Episode Highlights: How to Have Difficult Conversations

How People Usually Respond

When faced with a difficult conversation, most people respond in two ways:

1. The first type demands understanding from the other party, stating their beliefs but refusing to hear the other person. As a result, it becomes a one-way discussion that usually ends up in a fight.  
2. On the other hand, some people avoid having the conversation at all. This may come from their fear of conflict or not being able to handle the situation once it blows up.

Either way, we risk damaging the relationship when we fail to approach difficult conversations healthily. 

Courage and Emotional Intelligence

These two skills are useful in having difficult conversations and achieving the best outcome. 

Courage — If the other person is avoiding the topic, you have to take the initiative and broach the subject. We have to be brave and be the ones who bring difficult things out into the light with the people we love so that we can have relationships that are based on authenticity, respect, vulnerability, and compassion and connection.

Emotional Intelligence — If you can understand your feelings and underlying motivations, you can have more productive conversations instead of full-blown confrontations. Having high emotional intelligence means you can step back from an emotionally charged situation and assess the steps you need to take. 

Ask yourself these 7 questions to build and strengthen your emotional intelligence:

1. How am I feeling?
2. What are the thoughts behind these feelings? 
3. What do I need to do right now to shift my thoughts back into a constructive and compassionate mindset? 
4. What do I need to do to bring myself back down emotionally so that I am in a place where I can speak respectfully?
5. What are my intentions for this conversation? 
6. How would I like this conversation to end? 
7. Who do I need to be right now to make that happen?

That said, you don’t have to have difficult conversations with everyone. Identify key people in your life and let the rest go. When a relationship becomes toxic or abusive, set clear boundaries. 

Having difficult conversations is an investment in the people you want to have a future with. Thus, you need to focus on people worth doing this hard emotional work. 

Creating Connections Through Difficult Conversations

Once you’ve identified the people who are worth the emotional investment, the next step is to embrace the discomfort and vulnerability that comes with these conversations because communication patterns deeply shape our social connections, as research shows.

We grow through difficult moments. When the alternative of staying the same is ultimately less comfortable than the discomfort of growth, the only choice is to change. We can do hard things when we’re motivated to do so.

The goal of having difficult conversations is not to have the same conclusion. Rather, it’s about appreciating the other’s point of view and trying to understand why they think the way they do. 

In order to have happy and healthy relationships, we need to find common ground and learn to look at a situation through the lens, beliefs, experiences, values, and expectations of another. 

Keeping Your Emotions in Check

Before you start a difficult conversation, you need to understand how your brain processes emotions.

When we are overwhelmed or emotionally flooded, a part of our brain tends to shut down to protect itself. This part, where empathy is housed, becomes inaccessible during emotionally charged situations and confrontations. 

Thus, you need to develop social and emotional awareness to bring yourself back into a better headspace and continue difficult conversations. At the same time, you have to be aware if the person you’re talking to is emotionally flooded as well. When you notice that either or both of you are getting overwhelmed, take a break to calm down. 

The Pregame Checklist 

Before engaging in a difficult conversation, mentally prepare yourself through clarifying your thoughts and intentions. You can try talking out loud or journaling so that you enter into the conversation without too much negative energy. 

Here are 6 questions you can ask yourself:

1. How do I feel about the situation? Why do I think that way?
2. Why is this important to me? 
3. How is the situation impacting me? 
4. What would I like to communicate? 
5. What is my desired outcome? What would I do if that doesn’t happen? 
6. Do I want something to change or just to feel understood?

The Importance of Empathy 

After you’ve gone through your pregame checklist, the next step is to move past your internal narrative and run a mile in the other person’s shoes.

Here are 4 key points to help you in empathizing with others:

1. What are the core values of this person?
2. Where are they coming from?
3. What do they need to hear from me so that they feel respected and understood, even if we have some differences? 
4. What do I need to say for them to understand that they are valuable to me?

It’s not about achieving your desired outcome but looking at the situation from their perspective and understanding why it makes sense. When you really listen to another person with love, respect, and empathy, they do make sense.

What to Avoid in Difficult Conversations

These are 5 habits you should avoid when you’re in a difficult conversation. 

1. Refrain from the fundamental attribution error. It’s when you ascribe a person’s bad choices to character defects instead of considering the unique set of circumstances that led them to that choice. 
2. Avoid going into conversations seeking only to persuade someone or change their perspective. 
3. Keep away from judgmental and self-righteous lines like, “If you only knew what I knew . . .”
4. Be aware of micro-habits like eye-rolling or scoffing.   
5. Don’t go into a space of judgment and blame. Avoid interrupting and take the time to ask open-ended questions, listen, and understand. 

If you refrain from these lines of thinking and habits, the other person will feel heard and respected. Since they feel emotionally safe in your presence, you can have more productive conversations, and they will be just as likely to extend the same grace to listen to your side.   

If you are in a healthy relationship with someone that you have a lot of emotional intimacy with, it turns into an openness and willingness to exchange ideas. And if you have done a really good job of listening and understanding, that will be reciprocated. 

Further Support for Your Conversations

If this episode brings a specific conversation to mind and your stomach flips a little just thinking about it, I have a resource to support you. My Communication That Connects free training takes you deeper into the skills we cover here – practical do’s and don’ts for communication that creates understanding, plus real examples you can use with your partner right away. You’ll also receive a full workbook with lessons, activities, and homework to help you get to the root of conflict, calm reactive patterns, and build a more emotionally safe connection. 

And if you’re at the point where you don’t want to keep doing this alone, I’d be honored to support you more directly. At Growing Self, you can tell us what’s going on in your life and relationships, and we’ll help you connect with the right therapist or coach on my team. It’s a simple, private way to say, “Here’s what I’m struggling with,” and get matched with someone who can walk through it with you. Start that process here: schedule a consultation.

You deserve relationships where you can say the hard things, feel truly heard, and still feel loved at the end of the day. 💗

xoxo,
Dr. Lisa Marie Bobby