How to Handle Hard Conversations Like a Pro: 6 Practical Tips for Entrepreneurs

In this episode of Not Nice, Clever, we’re getting real about one of life’s toughest skills—having hard conversations. 

Nobody loves them, they’re awkward, and let’s be honest, they’re easy to mess up. But handling these talks well can make all the difference in your relationships, business, and sanity. 

We’re sharing six practical tips that help us tackle tough talks, from setting a clear intention (so it doesn’t turn into a blame-fest) to using “I” statements and learning to pause instead of blowing up. 

Whether it’s a tricky chat with a client, team member, or even a loved one, these tips are here to help you get through it with grace. 

Tune in, take notes, and let’s make hard convos a little easier together. 

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• Candice Carcioppolo
• Kat Torre

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Transcript

Hi, I'm Kat, marketer turned brand storyteller. And I'm Candice, educator turned entrepreneur. And you're listening to Not Nice, Clever. As CEOs and leaders, it's your job to always have the answers. But sometimes you need a little help. Leverage, if you will. We get it. This is the place for you. So wherever you're listening, 530 AM Club at the gym, on your way to your next meeting or putting out today's fire, let's get into it.

In today's episode of Not Nice Clever, we are talking about the hard stuff. More specifically, hard conversations, difficult conversations, because let's be honest, nobody loves them. They're not comfortable. You can't really get perfect at them or great at them. You just get a little bit better each time, but they're a necessary part of life and a necessary part of growth. So whether it's your team member or a client or a friend or a family member,

navigating the skill and building it like a muscle is really, really helpful. So we're going to devote this episode to talking about that, walking you through how we approach it, instances where it's popped up in our lives. let's get to the hard, hard, shall we, Candace? Let's do it. So we have kind of six bullet points that we created for this episode for you. six things that we kind of think about when we're going into these conversations, they can still be uncomfortable for Kat and I, but

I think over time, what we've realized is that the benefit outweighs how it might feel in the beginning. So we are going to share some things that have worked for us. So the first one is get clear on your intention. Before you dive into a tough conversation, I want you to take a moment to get crystal clear on what this purpose is, because it can be easy to make it a confrontation to be accusatory.

And that is not a purpose that is going to serve you in building that relationship or making the repair that needs to be made or moving forward. So instead of approaching the conversation, thinking about how that person did something wrong, it's thinking about the end goal of getting to where it is that you want to go together. Are you trying to accomplish a goal together? Are you trying to

save time or whatever the goal is, that's what should be in your mind not

what the other person did wrong maybe in your, how you perceived it. Yeah, because I think one of the toughest things about having difficult conversations is the emotion and trying to compartmentalize the emotion from the facts and also keep an eye on, like you said, Candice, the shared goal. Speaking when you're triggered, speaking when you're angry, when you're frustrated, when you're tired, when you're hungry.

It's just, it's never a good situation. So always starting there to kind of like neutralize the conversation.

Yes. So this might even be silly to you, but you might even just want to write down your intention for the conversation before you even go in it if that's possible. Because sometimes just seeing it written down will give you that clarity of why you're having this conversation in the first place and make you feel like you're actually moving towards that thing. exactly. So our next hit

is this is like going back to like relationship counseling 101. Even like conflict resolution, like on the kindergarten playground, I feel. But it bears repeating because it's very useful. And that is using I statements instead of like using you accusation. So instead of saying like, you're doing this, you're doing that, you didn't do that, you didn't think of this, you can turn it around and say, you know,

Here's where my head's at here, or this is how I interpreted went down, or this was the information I was operating under, or I felt really uncertain, unclear, surprised, whatever the situation is, take ownership for your part in it and just express from your perspective. Because the truth is, nobody really knows what goes on in another person's head. Nobody can read their minds. Nobody knows exactly what they're thinking.

You know when they did something and so you're you're assuming instead of just really speaking to what you are able to speak to Right. Yeah, I think that's so important also understanding people's unique positions and perspectives because for example Dom and I were talking this week and this was not a conflict but we were just talking about how we like the way we communicate with one another and one of the things that he

is doing is traveling a lot between now and when our baby is due. And so he has a goal in mind because he wants to be able to take off time. And so he's like trying to reach that goal. So he feels comfortable taking off a big chunk of time. And I have other goals because as the mom, I'm like, I want

to paint the house and I want to get the nursery together and I want to do all stuff. I'm in the nesting phase, right? And it could be easy for me to be like, Dom doesn't care because there he is going again to wherever he's going for work. And it could be easy for me to be like, I feel, I don't know, neglected or I feel this.

It's all of you or... Yeah, instead of saying, have goals that I want for myself and my family, our family, and he has goals that he wants for himself and his family, and both of them are important. And these are the two things that we need to do that are kind of different right now, but in service, ultimately, of the same goal. know? But I could see how it could get misinterpreted as like, maybe I'm being insensitive for his work,

But then also how he's insensitive to what I you're taking it for granted and he's not being there to support. Like all of that rabbit hole that could easily happen and come up. in my previous relationships, it might have. But now, because we communicate so well and we do have shared goals, it's easy to say, like, hey, this is our shared goal. By December, we want to be able to do X, Y, and Z.

And in order to do that, this is Dom's role in that and this is Candice's role in that. And are we okay with this, you know? So it really is important to be able to understand each person's perspective because neither of us are wrong about what we're doing. We just have different goals we're trying to fulfill or different aspects of it.

I think that's like another, would say like extension to this tip here is recognizing when you do communicate like this, it helps you understand and accept that actually, like truly, what I have found helpful is not thinking in terms of I'm right and they're wrong, or I did something good, they did something bad, because that's so subjective. It's all subjective. It's all just like through the lens of our own experience. So when you remove those labels,

And you just speak from how you're speaking, like what your goals are, and then he shares what his are, and then you find a way to like meld and integrate them in the best way possible. Yep. So much better. Right. Because ultimately, we have a bigger shared goal that each of our like little goals are in service of. know, so super important, be open to having that conversation. Another one is

Listen more than you talk. And what helps me in situations like this is get curious. Ask questions, but not questions that make someone feel bad, like questions that are coming because you genuinely want to understand, not because you are trapping them in some situation, right? Which I know can get, that could be easy to do.

ask questions out of curiosity to understand the person's perspective. And I think that will help you a ton. Yes. And most, most importantly, because I remember, and I know, Candice, if you were on this webinar, it was like maybe a year ago, where it was one that Ryan was co-hosting. one of our leaders that we work with, Ryan Serhant, he had this negotiation expert on and his name was Kwame. I can't remember his last name is escaping me.

But it was so funny because the whole theme of it was difficult conversations and negotiations and conversations and conflict. He talked about conflict like, you know, in the home, like between partners and then also at work between team members. And he was like, Ryan, I was like, let me ask you this. has your wife ever, have you ever said something to your wife and then you think you're saying it like at a normal actual decibel level, but then her responses, don't yell at me. And I busted out laughing.

Because this webinar was on too, I was like, yes. And everybody was going off in the chat saying, yep, yep, yep, yep, yep, yep, yep. And it's because, and Kwame explained, he was like, your volume of voice was not yelling at her, but the tone was yelling at her. And so I think with this tip in particular, when you ask a question, actually ask a question. Like when you ask a genuine question, there's an inflection at the end. Hey, Candice, can you tell me about what you were thinking about when this went down?

Instead of, Candice, what were you thinking about when that went down? Yeah. There is definitely... Right? Yeah, you're shutting that person down when you approach it in the wrong tone. Yeah. It's so big. So... This is also why you need to plan these conversations. Yes. Like, in your head, write it it heated. Yeah.

Write it down, get it out, make sure you know what your goal is, focus on that. Because if you go in too heated, it's going to be really difficult for you to manage your tone. This is with colleagues as well, right? It's with anybody who's a human. Yes. Even your animals too, even canines and felines. They can sense and even smell your tone from your hormone levels and your pharma. Go easy on your pets, people.

The next one is know when to pause and reflect.

I think one of my go-to's is kind of like filling in the space if there is any awkward pause. Yeah. And I'm trying to learn how to be okay with that maybe awkward silence that is necessary for people to gather their thoughts or for me to calm down or whatever it needs to happen. Be okay in that silence.

It's funny that you're sharing that, that sometimes you do that in like personal situations or whatnot, because as a teacher, I know that you have shared multiple times. You're like, when you're on a webinar, you're on a workshop or on stage and we're like asking questions, like ask the question and then just like, let it simmer. Yeah. And give them time and space to process and then formulate a response so that then they raise their hand or then they speak up and go off mute or whatever it is.

but not rushing to just go on to the next thing. It's a practice. It doesn't come naturally because as humans, you maybe get anxious when there is that pause. Like, what's supposed to happen here? Who's going to raise their hand first? Who's going to, you know, go? Who's going to be the brave one here? And it's so funny because this happened just last week where we are in the midst of

Getting settled into philly so like we moved and then last week was our first week of settling in and getting unpacked and getting to know the neighborhood and parking and there's like signs with street sweeping and there's only certain places where we can park and just all the things and also keeping up with business as usual. And I remember this was the funniest thing so like we have new fobs to write so we have new fobs to our new apartment. We still have the old fobs to our old apartment because we haven't turned those in yet.

And so we have all these fobs like on our table by the door and Will went left for work before I was getting up for work that one day, like, I don't know, day three or four of us being here. And he, he took the, my fob for this apartment thinking that like he saw the other fob and he thought that that was like my fob for this apartment, but it was my fob for the old apartment. So he got it like mixed up. so I couldn't.

have a way to get in and out of our apartment to move our car for sweet sweeping. So I called him. was like, I was like, where's my fob? I was like, it's almost 11. I have to move the car and da da da da. And like it ended up spiraling into this thing. And then like, I don't know, like a few minutes in, was like, I was like, I'm gonna call you back. I was like, I'm about to say something that I'm going to regret. I was like, and this is over a fob. I was like, I'm gonna call you back and let you know how goes. And I hung up. This is is just dress from the last.

three days of moving and not actually anything. not mad at you. I'm not mad at you. I'm not frustrated with you. was like, I'm going call you back when I can form sentences. Yep. And it was so helpful because sometimes in past situations, you've been in those situations where you just dig in and you go deeper and it's just not helpful. You're talking in circles and you can't think straight. And all of a sudden you realize you're in this conversation because you want to prove that you're right instead of solving the problem.

All right. The last one is end with actionable next steps. So it sounds like making a plan to get the fob from Will would have been setting an actionable next step. That would have been actually well, the first actionable step was getting off the phone because I was like word saluting and he was at work and he started a new job, you know, so he's trying to get his bearings and everything. was a recipe for miscommunication and conflict.

And so the next steps for me were get off the phone, take a deep breath, walk around the block for take a beat. And then I, and then once I did that, I was like, okay, I was like, I'm going to call the emergency maintenance, have them follow me into the building so that I can get back in there and not have a problem. And then I moved the car and it was funny. Like when I moved the car after I went back and I, there's a coffee shop right next door to our building, which I loved.

I walked in and I was telling them about the street sweeping and this and that. They're like, they're yeah, there are signs posted, but you got at least 15, 20 minutes. As long as you get your shit moved by then. I was freaking out at 1101 AM for no reason. No reason. But I didn't see that or know that after. So then I shared that with Will. I texted him. was like, I moved the car. We're all good. I got back into our apartment. Have a great day. We'll call you later.

But it's just, you know, next steps, like have clear next steps, because then the other person's not just like waiting on you, uncertain or unknown. Like when you're having difficult conversations, it's really good to have that bow on it. Yep. And even if you are taking that beat, it's like, hey, can we talk, can we revisit this tomorrow or, you know, just letting them know when you plan on revisiting it. That way, it's just not this thing that's lingering or hovering over anyone. Yeah, I think there's also

a good way to go into that next step without actually having to make a plan to solve the problem. The next step is we're going to talk about this again tomorrow. I think that would be really helpful and beneficial for the other person too. Yeah. And this is where you can use the I versus you statements. It's like, I'm not thinking clearly right now. I don't feel like I can be productive or come up with solutions.

If it's a loved one, you can be like, love you, but I'm not in a good frame of mind to have this conversation. Can we revisit? When I'm clear, when I can show up better, then you're not saying like, I can't handle you right now. Let's talk later. It's just such a different vibe. And with team members too, it's like, have a lot of respect for you. I want to solve this problem. I'm excited to. I'm very stressed. have a lot of other fires that I need to put out right now.

You are a priority and I want to prioritize this like at this point in time or something. like you've done this before Kat. I mean, you work with Ryan Serhan and other leaders like that. Like there's some fucking shit that comes up y'all. There is. Yeah. But it's all solvable. It is.

All right, so to recap some of the tips we have for you, if you are in a space where you know you have to have a hard conversation, one, get clear on your intention. I suggest you write it down. Plan out the goal of this conversation before you get into it. You never want to start a conversation when you're feeling heated. Once you do that, you want to make sure that you're creating a safe space. So things like using I statements, avoiding accusations, listen more than you talk.

know when to pause and reflect. And lastly, end with actionable next steps, even if that means let's revisit this combo tomorrow. So much better. If you have another tip that you have found helpful, because this is what's worked for us, but we would love to hear from the Clever Crew, feel free to slide into our DMs on Instagram at notniceclever. We'd love to hear from you. Thanks for joining us on Not Nice.

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