PMH 90 | Difficult Conversations


Difficult conversations are no cake walk, but we will all have them. Whether it is a hard conversation with a loved one or giving your notice for the first time, we all engage in these conversations in our lives. On this episode, Siria and Melissa will give FOUR reasons why you need to have those difficult conversations NOW. They explore why these conversations are hard, share some of their stories, and give you concrete tools to help you prepare.

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4 Reasons You Need To Have That Difficult Conversation Now

In this episode, you will learn four reasons why you need to have those difficult conversations now. We explore why these are hard, share some of our hard conversations, and give you tools to prepare you for these conversations.

I’m sure at some point in our lives, we all engaged in difficult or uncomfortable situations or conversations.

I try to avoid them at all costs.

Before we get into that, you and I were talking about the difference between assertiveness in business versus in our personal lives. If you were to ask me about difficult conversations at work, I’m all about it. I’m all for it. I’m very assertive there. I can have difficult conversations there because I feel I’m more comfortable in that space. For this episode, we’re going to look more at those interpersonal conversations, those difficult ones that you’re like, “I want to have them, but I don’t feel comfortable doing it.”

Even with what you were saying, I immediately went back to one of the first very difficult business conversations that I had, which was giving my resignation. I will share that story here in a bit, but I think that at the end of the day, we’re talking about this probably more of like a one-on-one conversation you need to have. It is something that is brewing, that needs to be talked about and that you have been thinking about for some time and we want to help you with that.

I was thinking about many things that can be considered a difficult conversation. I had a conversation with my mother about her death and what would happen after that. That’s a very uncomfortable conversation. We’ve also discussed crossing boundaries here on the show and talked about finances. No one likes to talk about finances. Any type of relationship woes, like you were mentioning, career changes or resignations. All can be very difficult, which is why I think it’s important to hit on this topic and explore why they are hard, why they are important and how we can start to feel more confident or comfortable in these conversations that are needed.

You touched on the fact that there are many different types of difficult conversations. Where should we begin?

I wanted to start off with why we feel that difficult conversations are so hard? Obviously, they’re not easy, but I was reflecting on myself. Those who have experienced traumatic events or whose inner critic is telling them they aren’t worthy or good enough to change the situation that they currently find themselves in struggle with these. As I was reflecting, three things surfaced for me as to why I personally feel difficult conversations are hard. First was my upbringing. I was not shown or taught how to have a difficult conversation, let alone a constructive conversation.

I remember a couple of years ago, my mom, who was on her own healing journey, would often say, “I’m tired of living in a family of secrets. I refused to let that cycle continue with my family.” I sat there and paused because I know that she was referring to her mom, brothers and extended family. I saw how my immediate family, my parents and my siblings, all engaged in this type of behavior. Despite growing up in an enmeshed family like I was, we did not share feelings, thoughts, or experiences we were going through at all. We were taught to keep all of that to ourselves.

I would agree with you that upbringing was part of it, but it was more because I was told not to argue with my dad. I was very specifically told, “It’s easier if you get along and go along,” which is part of the reason my therapist says, “I’m super agreeable. I need to work on being assertive.” This is a big part of it. I remember as I started growing, getting older and maybe getting into those teenage ages, it was very difficult to hold my tongue and not be able to express the fact that I disagreed with something or that I didn’t like the fact that they would say racist terms in Spanish that I’m like, “That’s racist.” They are like, “No, it isn’t.” I’m like, “It’s super racist.” As I’ve continued to speak up, now it’s like, “We can’t say that because Siria doesn’t like it. I’ll take that.” The upbringing was for sure a part of it and literally being told, “Don’t argue.”

We’re never asked like how we felt at all. I’m happy to report that my family is starting to work on it because we were all like in our own little therapy, but I digress. Number two, it requires that we revisit our past. My past was hard. If you’re anything like me, I’ve blacked out certain portions of my childhood because they were too traumatic.

I feel bad because people from my past will recall experiences and situations. It’s like I’m hearing it for the first time. We’ve talked about this show revisiting our past and how necessary it is to heal. When you’re thinking about these difficult conversations, like the difficult conversation I wanted to have with my dad required me to go back to that space where I felt abandoned, I was hurt and longed for my father.

When we’re thinking about engaging in these conversations, it does require us to go back momentarily because we’re trying to then move forward in terms of, “What is it that I would want from this conversation?” Another thing that holds people up is that it requires us to go back in order to go forward. Lastly, if you are a people pleaser like us, you fear rejection. I’m going to bring up my father. I have a huge fear of rejection from my father. If I said anything, I was afraid he was going to hightail it out because he had a pattern of doing so.

Difficult conversations require us to go back in order to go forward. Click To Tweet

This need for love and acceptance, especially from the people we hold most dear. I almost felt like love was very conditional back then. I would hold all of that in because I was fearful of being rejected. As a people pleaser, I was fearful of hurting other people’s feelings. I spend much time and energy putting other people’s needs before my own, and it leaves me harboring feelings of resentment, anger, unhappiness and pain. You cannot control how another person feels or reacts in any given situation, but holding onto that causes us more pain. The last one is if you’re a people pleaser.

I approached this question a little bit differently in terms of why we need to have these conversations. For me, the number one thing when we were brainstorming this topic was it was not going to get easier. The longer you wait to have this conversation, the more you replay it in your head and you ruminate. The more you spend this energy, it’s not going to get any easier. The more time that you’re spending here knowing, “It’s not going to get any easier.” You might as well rip the Band-Aid off and have that conversation. It’s not going to go perfectly but it is something that you need to get there. You’re only making it harder and you’re making a mountain out of a molehill.

PMH 90 | Difficult Conversations
Difficult Conversations: It’s not gonna get any easier the more time that you’re spending here just knowing. You might as well just rip the bandaid off and have that conversation.


It’s exactly what I usually end up doing, where things end up looking and feeling enormous. At the end of the day, I was like, “Oh.” My reason number two why you need to have this conversation is it will probably go better than you think. It happens to me time and time again when I think somebody’s going to blow up at me. I’m going to lose a friendship or completely have a meltdown. Whatever it is that my brain is very good at telling me is going to happen has never happened. It always ends up going much better.

I remember this one time. I was a teenager and living with my parents. My friend and I were getting out of a movie. It was a late-night movie and it was raining. I backed up into somebody’s car. In my head, I was like, “I’m going to get in so much trouble. Look at all these bad things.” Because of all of that, I did the responsible thing. I put a name, phone number and a note on the car. The entire drive home, I’m like, “I can’t believe I have to admit this. My parents are going to be mad.” I walk into their bedroom and they’re both watching whatever telenovelas are on. I explain my car crash. I was like, “I’m sorry, but I did the right thing and left the note.” This is how my parents reacted. This is where they were like, “You did what? Hell no.” My mom puts on black pants, a sweater and a hoodie.

They call to take this note away, I’m assuming.

Yes. She goes back to the movie theater, hoping and praying that the note and car are still there. It was the exact opposite of what I thought was going to happen. I thought I was going to get in trouble and all these other things, but no. Instead, my mom dresses up like a cat burglar. I don’t even know where she had the beanie. She doesn’t wear beanies. There was a beanie involved here like a Catwoman over here, going out there grabbing the soggy wet piece of paper out of the windshield. It was that difficult conversation you’re dreading that may turn out way better than you expect.

Isn’t that like a misdemeanor of hit and run?

The statute of limitation is run, which is why I’m able to talk about this publicly now. It’s one of those things where things are probably going to go better than you think. You need to be open for that to be a possibility. The final reason that you need to have those difficult conversations is you touch on it a little bit. Instead of worrying about the other person, you’re hurting yourself. The longer you stay in here and that negativity, it’s only causing you self-harm.

Here in the show, we’re trying to encourage you to love yourself more and be more self-compassionate. The last thing you want to be doing is hurting yourself. If you are not having these conversations but have them in your head, you’re talking to everybody about them, and how you need to do all this stuff, you’re keeping yourself in that stress cycle and those stress hormones in your body. You’re only harming yourself. Stop doing it.

I am going to add to it because you’re right. There are several reasons why having difficult conversations is important. A lot of what I’m going to say is going to dovetail off of what Siria has talked about, which is it’s never going to go away. What I’ve noticed are these negative feelings and thoughts that I continue to harbor. They fester and multiply. What happens at that point is it causes ripple effects in other aspects of my life. Here I have been talking a lot about my father. This hurt and pain left me guarded. It impacted my relationship with friends, intimate partners and all of this stuff. It didn’t serve me. It emerged and showed itself in a different way.

These negative feelings and thoughts that continue to harbor, fester and multiply. Then, it causes ripple effects in other aspects of your life. Click To Tweet

The second is harboring these feelings without properly addressing them can lead to emotional outbursts. My little Latina side will come out at the most inopportune times. I mentioned on the show before that I was trying to set up boundaries with my mother. Earlier, I mentioned how, growing up, we didn’t talk about feelings at all. That included my parents. Here I am trying to establish boundaries. Rather than being firm, I yelled. That anger piece came out because I felt like, for so long, my feelings, thoughts and emotions had been squashed and not heard. I’m going to shout them as loud as I possibly can because now you’re going to hear me. Was that the right reaction?

No, but at least I know that moving forward. Getting ahead of it so you don’t have these emotional outbursts because you might yell or say something that you don’t mean. Growing up, I was spanked as a child. Do I remember anyone’s particular spanking? There is one, but do I remember words that were said by my parents or someone? Those dug deeper because they said them out of emotion and the moment. Those stayed there with me longer.

When you’re talking about the emotional outburst, that’s usually what gets me. It’s the words. I distinctly remember being spanked once. My dad had his own meltdown about it because he’d never wanted to do that, which is ironic considering the whole way that I grew up. It was always the words. The words always cut deeper. This is one of the things that impact my relationship with my mom because she has her emotional outbursts when she’s been drinking. She claims not to remember them, yet everybody around remembers. I’m left hold in the bag of the shit that you said because you don’t have the guts to say it any other time, or you think it’s going to be excused, and that is some bullshit.

The third thing is it cripples your well-being because you’re unable to heal and move past it. I’m going to give an analogy for this. Suppose you broke your foot and the doctors put a cast on it. They recommend rest and physical therapy. Despite the doctor’s orders, you continue to work, go to the gym, run errands, etc., because the thought of resting and physical therapy is too much work for you at that moment. Your body will begin to work to heal itself.

The bruising will go away. Your bones may start to fuse together, but because you didn’t put in the work that was needed to heal correctly, that break didn’t repair itself correctly. Even though it may appear on the outside that your foot is healed, you may feel pain with every step you take. Because you appear fine on the outside doesn’t mean that everything is okay on the inside. If you truly want to heal and thrive, which we want you to do, it will sometimes require digging in deep and having these difficult conversations.

This is all great. I appreciate all of this information, but how do you do it? You have to mentally prepare yourself for it. It depends on the conversation. Earlier, I alluded to resignation and not like being resigned from life, but giving your notice. I want to share this story with you of how I did it and see if that helps you in some way. The first time I decided to resign from a job as a baby lawyer was hard because here I was. This place had given me an opportunity. I was in my feelings about this.

I remember I’m going to do all of the things that I can to prepare for this. I’m thinking about the words that I want to say. I want to show appreciation, but I also want to be firm about it. Our audience here probably has heard of doing the Superman pose and Wonder Woman pose, putting your hands on your hips. That is supposed to like increase your testosterone or whatever. That has been debunked and doesn’t work.

If you believe it, go for it. I did all of those things. I was breathing, standing in Wonder Woman pose and all that things. I’m ready. I’m going to call my boss right now and let her know, “Thank you very much. I wanted to give you the heads-up because you’re going to see this in your email. After this conversation, I’m giving you my two weeks notice.” I totally thought I was clear, ready to give this information over, and I can pick up the phone. I’m breathing, call her, ring, then voicemail.

I’m completely devastated because I’d done all of this work. I didn’t want to give my notice in writing until I had this conversation because, in my head, that needed to happen. Does it need to happen? I don’t know. It’s some social construct that I have adopted and had thought this is important for me to do. She called me back a couple of hours later, but I was not prepared for this phone call at that specific moment. I ended up telling her and I got super emotional. I was crying.

I didn’t realize how hard this was going to be. This was a difficult conversation. In my head, I thought everything was going to go fine and then here I was, letting her know. My voice is cracking and I can’t even breathe. I realize that for myself when I’m having a difficult conversation, I will physically manifest how hard this is and I have to breathe through it. It hits deep. Do what you can to prepare yourself, with the breathing and everything else, but also know that even with all of the preparation that you may have, you might still have a hard time, and that is okay. Don’t judge yourself for that.

PMH 90 | Difficult Conversations
Difficult Conversations: Do what you can to prepare yourself, but also know that, even with all of the preparation, you might still have a hard time and that is okay. Don’t judge yourself for that.


I’m going to come at you with some questions to reflect on. I do 100% agree about preparing yourself. That might take days, weeks, months, or in my case, decades to have a conversation with my father. You’ll know when the time is right. If you’re not ready, that’s okay. You’ll know when. I still have a few questions to ask yourself before any challenging situation, and I did adapt this from The first question is, “What is my purpose?” You have to be very clear. I’m going to share an example. When my husband and I separated, he and I were in marital counseling. I told him, “This isn’t what I want. I’m not happy.”

He’s like, “What would make you happy?” I was like, “I don’t know, just not this.” How unfair was that to him? Here he is, wanting to better the relationship, improve communication, and I can’t communicate what it is that I want. If you have a clear idea of what is the purpose behind this, which leads to question number two, “What do I hope to accomplish from this conversation? What would the ideal outcome of this conversation be?”

The fourth question is super important, “What assumptions am I making?” Sometimes we come into a conversation with assumptions that, “They never consider me. They always do something.” When you’re challenging your assumptions, you might find that, “I might have contributed somehow to this situation and how might I have contributed to this situation?” By remaining open, you’ll find, “Are there any common concerns?”

I might be feeling like I’m not being listened to by my husband, but he might be feeling the same way. If we’re both not feeling listened to, what can we do to allow each other to feel heard? By opening up conversations in that way, it becomes a dialogue. It’s not just me griping at you about why I’m unhappy. It’s coming up with a shared vision of a preferred future. How do we want to be in this space together? How can we create that together?

By having these difficult conversations and allowing that other person to contribute, you’ll be surprised at some of the ideas that they come up with in terms of how we can better ourselves. It reminds me of something you mentioned in a previous episode. It’s like, “I care enough to engage in this difficult conversation. It may be very uncomfortable, but it’s because I care about you and us engaging in that.” Asking these questions even beforehand or during is important. When we talk about preparation, that also has to go for the other person. You have to tell the person like, “I would like to discuss blank. When would be a good time for you?”

I agree with that to a certain extent because sometimes, that can be a double-edged sword where it’s like, “Let’s talk after work.” Sometimes people are like, “What did I do?” It’s like, “I want to talk to you about the podcast after this,” and setting an expectation instead of like, “We need to talk.”

I didn’t say that. I said, “I would like to talk more about the podcast. What time would be good for you?” You don’t want to catch that person off guard. We’ve talked about emotional consent. If you want that person to bring their whole authentic self to the conversation, you got to meet them where they’re at as well. It’s got to be a joint venture.

At the end of the day, what we’re talking about here is having difficult conversations with people who you care about. You’re not going to have a difficult conversation with the customer service representative. It’s not going to happen. You might have an interesting conversation, but you don’t need a prep for that. If you’re putting in this work and you’re thinking about it, that’s an indicator to me that you care about this relationship, whether it’s on a professional level or a personal level.

One of my favorite people is Brené Brown. In her Dear To Lead book, she talks about being clear is kind. This is what you’re trying to do. You’re trying to have clear communication of what it is that you want and maybe what’s not working. At the end of the day, it’s an act of kindness. It’s because you care about the other person on the other end or this relationship or about, “We’re breaking up.” Breakups are hard. Those ones have definitely been difficult conversations to have, but they’ve been conversations that needed to happen. Do the best that you can and give yourself permission to not be perfect about it because I don’t know anybody who has a perfectly difficult conversation. Do you?


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