How to Have Difficult Conversations

The Love, Happiness & Success Podcast with Dr. Lisa Marie Bobby

Music Credits: “Plastic and Glass,” Keshco

“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.

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. 

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.  

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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. 

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

Resources for How to Have Difficult Conversations

I hoped this episode provided a roadmap for having difficult conversations that strengthen connection and understanding in your most important relationships. Which part of the episode was the most helpful for you? Feel free to share your thoughts by leaving a comment down below.

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How to Have Difficult Conversations

The Love, Happiness & Success Podcast with Dr. Lisa Marie Bobby

Music Credits: “Plastic and Glass,” Keshco

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Dr. Lisa Marie Bobby: This is Dr. Lisa Marie Bobby, and you’re listening to the Love, Happiness and Success podcast.

[playing Plastic and Glass by Keshco]

Dr. Lisa: The band is Keshco with a song called Plastic and Glass—I thought it was a nice mood setter for our topic today. Today, we are talking about how to tackle difficult conversations in such a way that they go as well as possible.

It is important for us to talk about this topic because there are a lot of difficult conversations to be had lately. Particularly as we are heading into the holiday season in the midst of a contentious political season and with so many stressors and strains and angst and very real issues that people are facing. There is tough stuff to talk about with friends, with family, with partners, with siblings, with ourselves. And how you handle a tough conversation has a lot to do with the results you get.

So today we are going to be talking about why conversations feel so hard sometimes and strategies that you can use to face those moments not just courageously, but also with confidence and a sense of competence. And understanding some basic do’s and don’ts that will allow you to talk about important things we don’t want to hide, but do so in a way that helps you create the ideal outcome, which I think for many of us is to strengthen your relationships, increase connection and understanding and have it be a positive thing for all involved, as opposed to an unproductive conflict, because I think we’ve had enough of that in our lives. Right? So that’s what we’re doing today.

And if today is your first time listening to the show, I’m so glad that you are here. I am Dr. Lisa Marie Bobby. I am the founder and clinical director of Growing Self Counseling and Coaching. My background is as a licensed marriage and family therapist. Also, I’m a licensed psychologist, and I am a board-certified life coach. 

And I am here with you every week to talk about different facets of the life experience and offer you ideas and strategies and support that help you create the love, happiness, and success that you deserve in all the parts of your life.

And so today’s topic, we are going to be talking about a number, a number of things. We’re going to have, certainly, a lot of relational issues when it comes to difficult conversations, but also I think a lot of intrapersonal issues. You know. 

I mean, we have to get ourselves in the right kind of headspace, an emotional space, in order to handle these moments effectively. And also, I’m going to put on my life coach hat and offer up some specific strategies as well. So hopefully you leave our time together today with a plan.

So, jumping right in. Why do some conversations feel so hard? Think about the conversations in your life that you would maybe rather not have. Right? Think about what those are. Having conversations with your partner about some aspect of your sex life that you would like to have be different. Considering a necessary conversation with an employer or an employee around, “I don’t like what is happening here and we need to figure out a way to handle this differently together in order for this relationship to continue.” Right?

Many times, there’s, you know, married couples or partner couples, particularly with children. There are so many crucial conversations to have around parenting—“You can’t talk to me or the children that way, this is not going to work.” Or, I mean, my goodness, people who have very well-developed and sometimes even aggressive opinions about politics, social justice, issues around racism, and how to handle those moments in a constructive way.

It is very easy, when we’re faced with these kinds of moments, to fall into a way of communicating that can be very almost ultimatum-y. “This is what I want. This is what has to happen. And you’re going to hear what I have to say right now, whether you like it or not.” And that often doesn’t end well. That is a quick path to a fight, in all honesty. 

And there’s a way to handle this constructively that creates not just communication, not just collaboration, but, really, authentic connection. And that’s what we’re doing on this show today.

I am going to be loading you up with all kinds of resources today. So, either grab a pencil and notebook or open up a note app. Or you can also, if you haven’t already, bookmark the blog at, because a lot of the resources that I’m going to be giving you is kind of follow ups. 

So here’s where you go to learn more, are already on the blog there. In addition to these podcasts that I make for you, I have so many people, therapists and coaches on my team with me at Growing Self who are always cranking out articles and advice and tips on our blog at

And there’s so much around how to be a better listener, tips to communicate more effectively, how to manage your emotions when you’re starting to feel angry or stressed out. So, so much there. I just wanted to mention that as the go-to resource so that I don’t have to say it 150 times over the course of this podcast. 

But now that we’ve gotten that out of the way, when we think generally about what are the things that feel particularly difficult to talk about constructively, the things that we might even want to avoid or fear talking about, those are often the things that feel the most important. Those are the things that really need to be attended to, or resolved, or at least addressed. 

Because without that honest and courageous reckoning, our relationships will be fractured, and distance will grow. And unfortunately, that will happen whether or not we talk about it.

Many people avoid having difficult conversations because they are afraid of conflict. 

They don’t want to get into a fight. They don’t want to have an ugly interaction with someone that turns into a throwdown and wisely so—that is not ever helpful. And they don’t know how to handle the situation so that it won’t turn into a yucky feeling fight. So, they try to protect their relationships by not talking about hard things.

But the other side of this is that when you don’t talk about hard things that are bothering you, it will increase feelings of resentment, emotional distance. There becomes this feeling of separation and disconnection in your relationships—the relationships that you’re trying to protect by not talking about things. So, either way, there is a risk to your relationship, either through unproductive conflict or through avoidance.

It happens all the time. I can’t tell you how many clients I speak with, especially lately, who have perhaps a family member with a very vocal social media presence that is kind of diametrically opposed to their own political views. And say this family member is putting out lots of information that is incredibly triggering to say, my client. And they feel like they can’t talk about it because it will create this conflict. It will turn into a bad conflictual moment. So, they don’t, and instead, they avoid their family member. 

They make up reasons to not go down for a visit. They mute them on social media so they don’t have to see what they’re saying, which actually, just between me and you, may be a helpful strategy in this day and age. But they feel like they can’t talk about who they are and what’s important to them and kind of know and be known.

And so there’s this distance and avoidance and it will atrophy relationships in a very real way, especially for couples, too. If there’s issues going on in your relationship that you’re not talking about because you want to avoid the conflict. Those will breed resentment and this feeling of hopelessness and helplessness and, “Well, it’ll never be different.” And all of these kind of narratives around, “Well, that’s just the way they are.” That is incredibly destructive to a relationship.

So, I just mentioned all of these because when it comes to difficult conversations, the number one thing that we need, first of all, is courage. We have to be courageous and brave and be the ones that bring difficult things out into the light with the people that we love so that we can have healthier, more connected relationships—relationships that are based on authenticity and respect and vulnerability and compassion and connection. And it’s hard to do. It’s hard to do.

One of the reasons I have found that people often avoid confrontation. Well, first of all, what I mentioned is having, like, assumptions that it will turn into a conflict. They doubt their own competence to handle the conflict. They, and sometimes rightly so, believe that it’ll just disintegrate into an argument because they don’t know what to do to make it not be an argument.

So, let me talk about that for a second. There are ways of communicating with other people that will very predictably lead to an argument. 

For example, when you communicate with another person in such a way that is perceived as attacking or critical. The other person, just like the sun rises in the east, they will become defensive with you and they will start coming up with all the reasons why you’re wrong. 

It is very, very, very difficult for anyone to stay in the ring and have a constructive conversation when they feel attacked. And so, one of the things that’s really important to think about in these moments is how you are bringing up topics and how you might be perceived by others.

And so as so often the case in so many of our conversations here on the Love, Happiness and Success podcast, one of the most important skills that you can cultivate to have constructive conversations is the skill of self-awareness, particularly as it relates to emotional intelligence. Emotional intelligence means understanding, first of all, how you are feeling and what is going on inside of you that is leading you to feel that particular way.

So, for example, if you are high in emotional intelligence, you have more constructive conversations because you will be self-aware of the fact that, “Ooh. I’m feeling kind of angry right now.” And “I’m feeling a little bit upset. I am feeling morally justified in telling this person exactly what I think about them for all of these different reasons.” 

And you will be able to have that kind of meta awareness around, “Oh, my heart is starting to pound. I can feel even a little shaky. I am having all of these thoughts about why I’m right and why they’re wrong. And I know that I need to get myself into a better place before I attempt to have a productive conversation. Because if I go into it the way I’m feeling right now, the way that I’m thinking right now, it is not going to end well.”

And so, the core skills of emotional intelligence are being able to recognize: how am I feeling? What are the thoughts that are creating those feelings inside of me? And what do I need to do right now to shift my thoughts back into a constructive, compassionate sort of mindset? And what do I need to do to bring myself back down emotionally so that I am in a place where I can speak, not just speak respectfully, but also really genuinely maintain my ability to have compassion and empathy for the human that I am attempting to connect with right now, who is important to me? 

And coming back to, “What are my intentions for this conversation? How would I like it to end? And who do I need to be right now in order to make that happen?”

All of those are very deliberate things that people who are good at difficult conversations do very deliberately to keep themselves calm and kind of soft and centered and emotionally safe, even, to have constructive, connecting conflict—constructive conflict, believe it or not, is the thing. 

And I would also like to add that this is hard. It takes a lot of work on yourself in order to be able to get into this place and learn how to do these things. And you don’t have to do this with everyone. You might decide that there are some relationships in your life that are actually easier for you or even healthier for you to set boundaries around and go ahead and let that distance grow. As opposed to wading into this kind of emotional space with someone who is not going to reciprocate with you.

I wanted to bring that up because we’re talking about having difficult conversations with people and in relational contexts that are important enough and that you care enough about to do this kind of hard work, and those are the relationships that you want to invest in. That’s your family, your spouse, your child, a colleague or an employee or a boss who you really want to have a future with. These kinds of conversations, this kind of emotional work is an investment in your future—an investment in the future, in the well-being of others.

And I just would like to say that it is important to use discernment in your life and in your relationships to kind of assess where do you need to invest and work harder to understand, to be compassionate and connect. And where is it actually, not just appropriate, but important to set very real and firm boundaries with people and protect yourself.

So, for example, if you are with someone who is being overtly racist to you or others or who is using abusive language or treating you badly, you can go ahead and leave. You do not have to tell them why. You can just be done saying no. “No,” is a complete sentence. 

You don’t have to explain yourself, and you don’t have to do anything to make that person feel better about it. It’s your responsibility as a healthy person to protect yourself from toxic people, abusive situations, and to do what you can to protect other people who need protection from toxic, damaging, and abusive situations.

And so, I just want to say that out loud, because sometimes I will write things in the blog about how to be a better listener or how to have more empathic communication or situations like this, how to have difficult and important conversations. And we’ll get a comment on the blog about “Well, what about a narcissist who does these horrible things to me.” And it’s like no, that is a person who you need to set very firm, clear limits with. That is not a situation that is likely to be mended no matter what you do. And to be able to develop kind of the judgment to know the difference.

If you would like resources on boundaries, how to set boundaries, how to have healthy boundaries and still have friends, how to set boundaries with family members, how to avoid unhealthy guilt when you’ve set appropriate boundaries, again, I would refer you back to the blog at for podcasts and articles on all of those topics.

But this, this is how do we create connection through difficult conversations. So, we want to be courageous, but not indiscriminately courageous and putting ourselves into bad, bad situations. 

One of the things that I have found when it comes to these moments, when a relationship is worth investing in, it’s important to me and I know that I have to be brave and talk about something hard, I have found a thought that helps me, and it might help you, too. So, I’ll mention it. 

The idea that this is how we grow. We grow through difficult moments. We grow when we are challenged to grow. We grow when the other alternative of staying the same is ultimately less comfortable than the discomfort of growth. We grow, we change, we do hard things when we’re motivated to do so. 

And so I just want to offer that as an idea to you, that embracing the discomfort of these moments and breathing through it and reminding yourself that this is what growth and connection feels like is being authentic, being vulnerable, feeling hard feelings and doing the right thing anyway. This is the path of growth.

And also, I think sometimes reminding myself, if I want to have a high-quality relationship with this person, this is what I need to do. We have to talk because I know that if I don’t talk, I will withdraw. That’s something that I need to remind myself of personally. And I see a lot of my clients struggling with that. The tendency to avoid and withdraw can be pretty significant and to just be very explicitly reminding yourself, “No, this is important, I have to do this. If we don’t talk, we will become distant.” Those are ideas that can help you find the courage to do it.

Another idea I’d like to share that is really helpful for many of my clients, both individual clients and also a lot of the couples counseling clients that we work with, is that the goal of any of these conversations is not necessarily agreement. We do not have to agree with each other about the solution or the perspective or what is the truth with a capital T. 

What we do need is a sense of mutual understanding, to be able to say, “When I look at the situation through your lens, through your belief system, through your set of life experiences, through your values, through your expectations, I can understand why you would feel the way that you do. That makes sense to me.” And for you to feel the same. That even if someone doesn’t come to the same conclusions that you do about the same situation, that you feel that your perspective is understood and respected as being valid because it is. That ultimately is the goal. 

If we want to take that a step further and get bonus points, we could even move in to a space of appreciation that it’s not just “Yes, I can see why you would feel that way.” It is “You know what? I appreciate the values and the perspectives that lead you to feel that way. Thank you for sharing those with me.” Appreciation is even more, I think, affirming and conducive to emotional safety and constructive conversations.

And then, in addition to these ideas that can sort of help you grapple with conceptually what needs to happen in these moments of difficult conversations, a lot of my clients, either life coaching clients, relationship coaching clients, therapy clients, often find that it is much easier for them to have difficult conversations and be appropriately assertive when they’ve gotten really good at managing their emotions and going back to the emotional intelligence skills that we talked about in the beginning.

And so being able to have strategies in place to help you manage your emotions, understand what kinds of thinking or behaviors lead you to feel anxious or angry, and having a little toolbox of skills and strategies in place to help you feel calm is half the battle. If you can stay calm in a difficult conversation, chances are very good that it will be a productive one. 

Resources for you in that, I mean aside— you’re always welcome to do individual counseling or coaching. But if you have found that those are, let’s say, growth opportunities for you, I would refer you to the Happiness Class on, which is essentially an online cognitive behavioral skills training course that teaches you what are the kinds of thoughts that will make you feel angry, sad, or anxious. How do you shift those into more productive ways of thinking? What do you do with big feelings so that you don’t always have to be reactive or withdraw in these moments? 

So, to kind of boost up your skill set for being able to do that, because it’s really, really important when anyone gets flooded—you, me, everyone we know—gets emotionally flooded and begins experiencing intense feelings of anger, pain, fear, anxiety, what happens is that their brains, our brains, change in the way that they function, like literally. 

When you are flooded emotionally, you go into a fight or flight space that is very much prioritizing your personal protection. And what it looks like is that people will withdraw and not be able to talk anymore, or they go into attack mode.

Interestingly, the way that your brain changes in these moments is that the most highly evolved and most human parts of our brains—the newest parts of our brain structure, the neocortex—the part where we’re able to have empathy for others, the part where our language skills are housed, the part that allows us to take a big picture perspective or do any kind of if-this-then map kind of advanced planning, our executive functioning skills. All of that in very literal ways, shuts down and becomes inaccessible to you. 

And so, it’s incredibly important to be able to regulate your emotions during difficult conversations so that your brain doesn’t turn off and you turn into some sort of like crazed defensive or hostile, like lizard brain activated person. Because that sounds crazy, but that is actually what happens.

You see it all the time in couples counseling. A partner will say something that is clearly very triggering for their spouse, and that spouse will not— it’s like they just freeze. They can’t even continue in the conversation. 

In addition to managing your own feelings in these moments so that you don’t become flooded, it is incredibly important to develop the social and emotional awareness skills to notice when the person that you’re talking to is becoming flooded because they won’t be able to have a constructive conversation with you if they kind of go past a point of no return.

Some people, it’s pretty obvious when they become flooded. Their little faces get red. They might even start like shaking. But interestingly, men often become flooded and you would never know to look at them. They just kind of shut down. If you put a pulse monitor on their finger in that moment, it would be going at like 110 beats a minute. But to just look at them sitting in a chair, nothing has changed. You can’t tell the internal experience that they’re having. And that that is certainly true for many women as well.

 But being aware of when people are getting flooded and noticing that and having a plan in place to attend to it and help bring everybody back down is another incredibly important concrete skill to have in your toolbox when you are wading into difficult conversations. And being able to say, “You know what, I think we’re both getting tense. Let’s take a break. I’m glad that we started talking about this. I hope to continue the conversation with you. But I think, yeah, let’s go get a lemonade. Come on. Let’s go get ice cream.” Or something like that. Just kind of like shift away and let everybody calm back down again.

For more on that subject, the blog has a fabulous article written by one of my colleagues, another family therapist named Lisa Jordan, who has written an article on emotional flooding and has even more strategies for what to do in those moments when you become flooded or when your conversation partner becomes flooded.

So, there is a lot of pre-work to do to prepare yourself to have a difficult conversation. The pre-work involves the emotional intelligence skills we’ve been talking about and being able to regulate yourself, keep your thoughts in a good place, have the most noble intentions in the forefront of your mind, and also have a lot of empathy for the person that you’re talking with and an awareness for them. 

But also, I think when a conversation is really important, it’s always a good idea to do a little bit of almost pregame pre-work around, “Okay. How do I feel about the situation? Why do I feel the way that I do about the situation? Why is this important for me? How is the situation impacting me?” and get really clear around what’s going on inside of you and what it is that you would like to communicate to the person that you would like to communicate to.

It sounds so silly, but thinking through this stuff in advance will help you be able to not just communicate your truth effectively, but take some of the emotional energy out of it so that when you say, “I’m feeling really hurt and disappointed that we haven’t had sex in three months, and I miss you, and I would like to be with you.” If you’ve kind of written through what’s going on with you, why it’s important, what you want, when you say that out loud, it will be often like just a more gentle kind of way that is more understandable to the person that you’re speaking with. 

If you wade into a difficult conversation without getting clarity around that in advance, it is very likely that the energy and intensity that goes along with saying those kinds of things for the first time will be perceived by the other person as critical, blaming, or even hostile or attacking.

That is one of the reasons why talking about what you want to talk about in advance with a coach or a therapist can be so helpful. And that is not the only way. You can also certainly do journaling and get this clarity on your own. But if you’ve said it a time or two to someone, then you can go into the real conversation just from a space of calmness. And since the intensity is already less, it sets you up to be in a position to be a much more receptive listener, I think, because that’s hugely important.

So, doing some pre-work around, what do I feel? Why is that? What do I want? And getting really clear, too, around what is my desired outcome when we are done talking about this, what would I like to have be different? Would I like something to change? Would I like to feel understood? Would I like to have more understanding of this other person? Would I like just to feel more connected and like we’re not tiptoeing around each other or not talking about the elephant in the room? Is that my goal? It’s all okay. But to get clear about that ahead of time.

Now, you think that’s hard? Let’s talk about what’s really hard because the other critical piece of having an effective, constructive, difficult conversation means moving past what’s going on with you and how you’re feeling and what you would like to talk about, and what is your desired outcome, and setting that aside. And before you even get to that conversation, doing some very serious work around, what do they feel? 

This person that I want to talk to about these things that are bothering me, what’s probably bothering them? Why do they feel the way that they feel? What are their core values? Where is this coming from? What kind of relationship do they want to have with me? What did they need to be hearing from me in order to feel respected and understood and validated and valued and that they’re important to me? And what do I need to be doing, and not just saying, in order to show them that I care about them and that I love them and appreciate them, even if we have some differences.

And that, my friends, is hard work, it really is. It requires a lot of not just compassion and good intentions but also really accurate empathy to be thinking about how someone else probably feels and their thought process and in a way that allows you to make sense of it. 

This, I think, is particularly important in this day and age when there’s so much polarization around political kinds of things. It’s also very, very easy for couples to get incredibly polarized around who’s right, who’s wrong, what should we be doing. And it’s difficult to get on to the other person’s side of the table, and that is also a crucial skill and well worth your time doing some soul searching around in advance.

In my therapy and coaching sessions lately with clients, there’s been a lot of discussion around either both with couples who have different perspectives and belief systems or individuals around how do I maintain a relationship with someone who has a very, very, very different belief system than I do and one that I might even find morally offensive and just absolutely wrong? That feels like an affront to what I believe people should be. How do I stay connected to this person? 

And I would invite you to go into a compassionate, empathetic stance that allows you to understand the noble intentions and the highest and best of the belief systems that create the outcomes that you see, even if those outcomes are in practice, sometimes really damaging, damaging to others.

So, for example, and I do not want this to turn into a political conversation at all, but I just wanted to provide you with a model just for ideas to think about. A stereotypical Republican say, kind of belief system at the highest and best says something like, “I am a hardworking, responsible person who I have tried really hard to make good choices and I have a pretty good life because of it. I believe there’s a right way to live. And if people take the hard and narrow path, they usually have good outcomes. And that I believe in my belief system and I think other people should too. 

And I think that when I look around and see other people having bad outcomes, it’s often because of their own doing. And I shouldn’t have to pay for it or have the government swipe half my paycheck in order to support the bad behavior and poor choices of others. I think they can do better. And I think I have the right to defend myself against people who want to take advantage of me. And if I work hard and make good choices, I should be rewarded. And I have all these other belief systems that place value around life and family.” All these other things that when you go into it, noble intentions, noble intentions. And to be thinking about how does this make sense from this person’s perspective?

And on the other side, the same person on the other side of the couch, who maybe has a more progressive orientation would say, “I believe that human beings have inherent worth and that there are many different perspectives and ways of being that are all worthy of respect and appreciation. I don’t think any of us have a monopoly on the way, you know, ‘the way things should be’ or who is valuable in our society and who isn’t, because there is a bias and a hierarchy of value that is often based on race or socioeconomic status. There’s an unequal playing field. 

And the people with enormous privilege have a much easier time and often take credit for things that are handed to them. They think it’s about their character and their hard work, when they’re actually standing on a platform already.” Progressive people would say, “I think it’s the responsibility of an ethical community to provide support and assistance to those less fortunate in order to help build a large and fairer body of productive and valued members of our community. And that when we invest in people and things like education and health care, mental health and social services and firemen and police and roads and schools, everyone is lifted up. And that I’m willing to participate in that and help create that.”

So that’s one little example. And me just kind of like shifting from one side of that argument to the other. But in doing so, the hope is simply to share what the internal working narrative of people is often who are on different sides of this divide. And how when you look at the same situation from each point of view, it does make sense, even if you don’t agree with a belief system or the outcomes or the values. 

When you really listen to another person with compassion and respect and empathy, they do make sense, they always make sense. And I personally believe that we all could benefit from having intentional conversations with the goal of understanding those perspectives and seeing the good and the humanity in everyone, as opposed to reinforcing our ideas about why I’m right and you’re wrong.

Same thing for relationships. And as a couple’s counselor, I can assure you that when I am working with a couple and each person on opposite sides of the couch is feeling victimized and mistreated and hurt and uncared for by their partner, when you walk into their perspective, you can understand why. You can absolutely understand why and that none of us has a monopoly on the truth. 

And that it’s very, very easy for us as individuals to get caught up into our perspective and our way of seeing things. And there’s a very well-documented bias in social psychology where when we see other people doing “bad things” or making “bad choices,” or experiencing difficulty, we view it as because of character flaws, bad choices. It’s very easy to judge others.

When we make mistakes and have consequences or negative outcomes, the tendency is to say, “Well, but I was tired.” “Well, yes, but here’s the situation that led me to react that way.” We have all kinds of reasons why we do the things that we do because of the context of what was going on, the circumstances that made us feel that way, all of the reasons why we did what we did. 

And I think it would be to everyone’s benefit in this day and age to bestow the same grace to others that other people who are saying things or doing things that you disagree with have reasons and have a context and have feelings that make those actions or ideas make a lot of sense to them. And our role in difficult conversations is to learn what those are. Not have the focus on necessarily being understood, but putting the emphasis on understanding.

I know this sounds paradoxical because often the thing that motivates us to have difficult conversations in the first place is the hope that we could be understood, that we could change somebody’s perspective, that we could have a different outcome for the benefit of ourselves. 

And while that is certainly valid and generally the motivation that leads us to have courage and wade into these conversations, I would like to offer you a perspective that is much more likely to help the situation end well and lead to all of those desired outcomes. And that is putting your attention and effort on understanding the perspective and feelings of another person. 

Asking open ended questions where you invite them to talk more about their perspective, without being ready to be like, “Okay, well, thank you, because that’s why this is wrong.” And arguing with them or blaming someone else for the way that you feel or this one conversational strategy I often see, which is taking the sort of pedantic tone, which is that “If they knew what I knew, then they would change the way that they believe and, you know, all this stuff would stop. They would finally see the light.”

But again, like coming into that with a sort of judgmental and self-righteous idea, which is “My way of seeing things is better than yours and so, you should be more like me.” 

And this is true for everyone. It is true for progressives who really want to talk about diversity and inclusion, unless you’re an evangelical Christian, because that is not okay, right? And on the other side of this, for people to be absolutely resistant to any ideas about social justice issues or race or culture and the very real impact on people because of that and how they, by virtue of their own privilege, are participating in those things, whether or not they know it consciously, shutting all that down. It’s when we get very, very polarized and like, “No, I will not tolerate this point of view. I will not let in what you’re saying.” That is when conversations just go down the tubes.

And so, to be very, again, self-aware of how when you were having a difficult conversation and feel yourself going into that sort of space of judgment or blame or criticism or “let me rebuttal your idea,” would encourage you to move into a space of listening and understanding, open ended questions that are really focused on helping the other person feel heard and respected and cared for by you so that they feel emotionally safe with you and are able to talk about who they are, what they believe, the things that are important to them, and finally be moving into a place of what kind of relationship they would like to have with you.

And also in that space of compassion and emotional safety that you create, it creates an environment where if you are in a healthy relationship with someone who loves you and cares about you as much as you love and care about them, it turns into this openness and willingness to exchange ideas. That if you have done a really good job of listening and understanding that in a healthy relationship, that will be reciprocated. 

To be able to say, “Thank you so much for telling me how you feel when I see it from your point of view, I understand why that makes sense. Is it okay if I share with you how I have been viewing this and what my values are and why this sometimes feels distressing for me when these things are happening, particularly in the context of our relationship, which I care very much about, by the way.” It’s hard to have someone be like, and rare, I will say, to have someone say like, “No, uh-huh. Nope. I have just told you how I feel and what’s important to me, but I will not actually be reciprocating that.” That is very, very rare.

And if it actually is happening in your relationship, I would invite you to consider how mutually respectful and healthy that relationship actually is because relationships should not be one way. And if you are going into interactions with people with very not just sincere intentions, but strategies and skills like the ones we’ve been talking about today, you have the right to be respected and to also be heard, not necessarily agreed with, but understood. There needs to be reciprocity there.

So, there are so many other little micro-skills that I’d love to give you. And it’s beyond the scope of this podcast. But go back to the blog at and look— communication strategies and you’ll find all kinds of podcasts, articles, little things that you might not even notice there. Like, are you making little faces when other people are talking? Are you rolling your eyes without even realizing it?

You would be amazed at how many times in a couple’s counseling sessions, I have to say to one partner, “What are you doing with the faces? Come on, let’s stop that.” And really, they’re not even aware that they’re doing it, but making little faces or the eye rolls their partners being like, “Never mind, I’m done. They’re not listening to me. Why even bother?”

So, it’s these little micro-moments. And again, it requires so much self-awareness to stay in a good place, stay open, stay receptive, not make the faces. You know what I’m talking about. Certainly, things like interrupting, jumping to conclusions, rushing to defense. I mean, there’s so much. There’s so much. 

If you are in a relationship that is very important to you and you are trying really hard to have constructive, productive conversations, and it is just not going well over and over again, that would be an indication. It’s probably time to get some professional help so you can be sitting with a relationship coach who’s saying to either of you, like, “Stop with the faces, what’s going on?” And help with some of the core beliefs or jumping to conclusions or helping around, like listening skills, developing empathy for each other. If that’s feeling super-duper hard to do on your own, always okay to reach out for help.

And also be generous with other people who may not have had the benefit of listening to this podcast or doing the kind of personal growth work that you are so clearly invested in. Just the fact that you’re listening to this right now and thinking about how to have difficult conversations with courage and competence just says so much about you and realizing that I think when you grow in this area, it becomes really obvious when you see other people struggling in these moments. 

You can see them becoming flooded. You can see them becoming defensive or shutting down or feeling blamed, not knowing how to calm themselves down or switch back into more noble or empathetic thoughts. So these skills are hard one, but yay to you for doing them. I know there’s so much more that we could talk about on this topic and maybe I will record another podcast along these lines again in the future.

But if you have been someone who has recently emailed me or gotten in touch through Facebook or on the blog at or Instagram with a question about how do I handle talking to my elderly white aunt about her sort of internalized racism? How do I have a very difficult conversation with my boss or my best friend about something that is really bothering me and feels like it could tank our relationship? Or how do I broach a very important subject with my partner who I love very much, but about a situation that feels kind of unsustainable for me in our relationship?

I just want you to know that I have heard your questions and considered them very carefully. And I hope that the information that I shared with you today has provided a roadmap for how you can have the kind of conversation that you want and have it go well and lead to increased connection and understanding in some of your most important relationships.

And to thank you so much for listening today, if you have questions for me or anything that I can help you with, you are welcome to get in touch with me on the blog at You can also track me down on Facebook,, Instagram, @drlisamariebobby.

I would love to hear from you so that I can make a podcast for you. That’s all for today. And I’ll be back in touch next week with another episode of the Love, Happiness and Success podcast.

[playing Plastic and Glass by Keshco]

Therapy Questions, Answered.


  1. Thank you for publishing this article, it is really helpful. I am trying to use strategies that you mentioned for friendship with my best friend. If that’s the case, what is one thing that I should remember when I am having difficult conversation with her? I would like to make sure that the conversation with her would be productive without making it worse. I would appreciate your thoughts on this.

  2. Hi there, thank you for reaching out. I’m so glad to hear you’ve found the episode helpful and useful! I’m glad to know you’re using the strategies from the episode. If there’s one takeaway, I’d say it’s practicing feeling your feelings and emotion regulation even outside of having difficult conversations. These are skills we can strengthen with practice! You might find the episode “How Difficult Emotions Lead to Growth” a helpful addition to the great work you’re already doing. Congratulations! ~ LMB

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