In this episode of the Happiness Challenge, Klaudia speaks to an executive coach Chris Wong to dive into one of the most challenging yet transformative aspects of any relationship: difficult conversations.

Whether it's with a colleague, partner, friend, or family member, these tough talks are often avoided out of fear, but they hold the key to deeper connection and lasting happiness. They explore how embracing uncomfortable discussions can strengthen trust, resolve underlying issues, and create more emotional intimacy.

Join them as they share practical tips on how to approach difficult conversations with empathy, honesty, and courage—so you can build stronger, happier relationships.

This episode is PART 1 of May's theme: Difficult Conversations.

Hello, happiness seekers.

Welcome to this happiness challenge, where I'll be exploring the power of difficult conversations to build stronger bonds and create more happiness in our relationships.

Helping me with this topic is Chris Wong, an executive coach who helps build highly performing nonprofit cultures and is a co host of a fantastic podcast called the Art and Science of Difficult Conversations, where with his co host, Chris role plays various scenarios, from workplace conflicts to personal disputes.

And today, Chris is going to share with us how to approach difficult conversations with empathy, honesty, and courage so that we can build stronger, happier relationships. Welcome, Chris.

Hey, thanks for having me. I always feel humbled because it always sounds so more impressive than I think I am.

Okay, so, Chris, let's start from the beginning. What would you consider a difficult conversation?

Yeah, a difficult conversation at the most basic is a conversation where you care about a specific outcome and a relationship happening.

So in work situations, you may not care about being best friends with the person forever and ever, but you do care about the relationship being a good working relationship, and you care about being able to work well with this person. And so when you care about both, suddenly you feel anxiety when the thought of that conversation has come up. You may even put off the conversation.

You get into the conversation, and then every little thing throws you off. They get angry or they get upset or they say something that triggers you. You can't even focus anymore as.

Because you care so much about that relationship and that outcome that you're stuck. And I think that's. At core. At the core, that's what it is.

Yeah. I think this is so true.

And I think there is always that level of being vulnerable with another person, and therefore, it's quite scary to be so vulnerable. And because you don't know whether the person will accept that or maybe reject that. So I think I agree.

The more we almost are invested in the relationship, the more difficult certain conversations may become for us. And maybe sometimes we will overthink and therefore maybe avoid them. So that exactly leads me to my next question.

Why do you believe people tend to avoid those difficult conversations even when we maybe know that if I would have this conversation, my relationship would improve and there will be positive outcomes, but we still shy away from going into those conversations.

Yeah, there's a few different things. One is we're scared of those bad outcomes. We're scared of the other person getting upset or angry, so we just avoid it.

Second, we're just taught from a young age we might be a person that we were always taught, avoid conflict, don't talk about difficult things, always Be super nice. And so we just avoid having that hard conversation that we need to. A third thing is somebody just might not know what to say.

If I need to have a hard conversation with you about your performance, if I'm your manager, I might literally not know what the words to say are. I might not know how to give feedback. I might not know what the next steps are, how to handle if you get upset. Like, I may want to.

I may be like, yeah, I'm super comfortable with hard emotions. I just don't know what to say to move the conversation forward. So those are the.

I think the biggest thing like that they get in the way of people actually getting into conversation.

Quite interesting, Chris. Thank you.

Because you're speaking about this, maybe my internal fear of how I'm perceiving those conversations, but then you also speaking about that skill level in very simple terms, what do I sometimes say? How do I word it? In a way that is kind and compassionate towards another person.

So I love the fact that you think you're really speaking about those two aspects. The my internal mindset towards convers, difficult conversations, but also that skill level.

And in your podcast and in your work, you very much encouraging us and you are talking about that notion that actually difficult conversations is what we need more of. How do difficult conversations contribute to that personal growth, to that more happiness, more fulfillment at work and in personal relationships?

I think truly it's one of those backwards things where people feel like you have to have a good relationship with somebody in order to have a difficult conversation. And in reality, it's those difficult conversations that create bigger, deeper relationships with the people around us.

Talking about our favorite movies is nice, right? If we're building friendships, but then also talking about our families, what's important to us.

You know, those things are sprinkled in throughout most of our friendships, like those hard conversations that we have. And most of the times we're friends with people because we agree with them, and so we get along and we're willing to hear them out.

And even if we have things we disagree about or we have to give harsh feedback to somebody, that's the kind of stuff that builds that deeper relationship. Because now if you do the conversation well, it's building trust.

It's building that safe container where you're where somebody's going to feel like, oh, I can trust you.

I can trust that you have my best interest at heart because you're handling this conversation well and we're able to discuss it and truly understand each other better. That's Part of it also is we're having this conversation in a way where why we're doing the things that we're doing at what needs to be different.

And then we work together to figure out what that looks like.

Wow. Fascinating.

I must say, I never really thought about this idea that we getting it backwards, that we feel we have to build all of this legwork and then I'll have the difficult conversation. Rather than thinking the difficult conversation is actually helping me to build that trust and that stronger bond.

It feels like there is this block between people and because we're not having those conversations and no one wants to make that first step and we tiptoeing around certain relationships, whereas actually clarity and being honest is kindness. Okay. The first thing we need to do is actually sometimes have those difficult conversations to build those relationships.

But I think I personally sometimes struggle with the fact whether that conversation is worth a hassle.

Sometimes I personally feel like I'm not sure whether I will get the benefits and actually whether the effort and energy that I will put into having that conversation, will that actually yield me the outcomes I'm after. So how we can actually recognize that having that conversation is worth it?

I think that's a great question. And partially it's dependent on multiple factors. Number one, is it a personal conversation or a professional conversation?

And also thinking about the long term and part of the preparation is what is the outcome I'm really looking for? And you said like, how do I know I'm going to get the outcome I'm looking for? Partially.

Sometimes people don't actually know what the outcome they're looking for is. They actually get the outcome confused.

Do you want to just vent at the person and just share that you're upset about certain behavior they're doing or something they're not doing? Or do you want them to change behavior in a very specific way? Can you achieve them in the same conversation?

Maybe it depends on how strong of a relationship you've already had in the past and how much time you have to devote to it. But I think part of it is being realistic. What is it that you actually want to achieve in this one conversation?

If you want to change somebody's mind about politics or how they're going to vote on something, that's not going to be a one time conversation, that's going to be a longer conversation. So sometimes the outcome of the one conversation is just building steps to a larger outcome that you want.

And so being realistic about that is, number one, is what is the actual reasonable outcome that I can actually expect. And then secondly is thinking about how important is this to me personally? I'll give you an example from my personal life.

When we first had kids, for anybody that's had kids, those first year is very difficult. The first year is very stressful. And I'm doing my best to help out around the house.

And there's part of me that's thinking, I feel like I'm doing a lot of work. Why isn't my wife putting in the same amount of work that I'm.

This is me confrontally after a while I was thinking, do I need to talk to her about this? But also in 10 years while I still remember this specific situation and how frustrated I feel and I was like, you know what? I really won't.

I'll just forget about this in a couple of weeks, I won't really care. And so then I didn't bring it up because I was like, you know what? I feel like we're both doing the best we can.

It doesn't really matter how much work I'm doing right now at this moment.

Now if it's another issue that's like I've been thinking about it for weeks and weeks upon end that I realized it's really eating at me and it's going to be harmful if I don't talk about this. Then I need to talk about it.

And there's other aspects of our relationship that I have talked about with her we've brought up to talk about and it becomes a better conversation about. This is why it's important to me. But same thing in the workplace. Is this something that really irks me, really bothers me.

So things like somebody didn't hold the door for me when I was walking into the building.

If they say thing in a meeting, like they keep interrupting over me or they say a demeaning joke that's meant to be lighthearted, but I'm taking it as hey, it doesn't feel good. I want to bring that up because that matters to me a lot more than did somebody remember to hold the door open for me one time.

So it's a mix of how important is this to you? What's a non negotiable for you that you have to talk about this and then also what's realistic in the conversation that you can achieve?

Great. And that already really shows us that before we go into those difficult conversations, we really do need to do some preparation.

Unless as you're saying it is I just want to vent at you because you hurt me And I just want to be heard. But even that, how am I conveying that message? Is the person going to understand what is it that I'm trying to say?

So really interesting about that being realistic. Really valuable to think about the outcome I'm trying to have. And as you said, what is non negotiable for me or what can I. Okay, let it go. Great.

So I'm sold. I'm going to have that difficult conversation. We already mentioned few techniques in terms of I'm preparing for it, I'm thinking what is the outcome?

How do I want to convey this, convey my message?

But what other effective strategies would you suggest for approaching difficult conversations so that we are increasing the chances of them being resolved in a positive way?

Everything we talk about our podcast, you'll listen to our podcast. I would say this is the best thing you can think about is number one, start the conversation saying exactly what you want to talk about and why.

Don't start with we need to talk. Or if it's a work situation, I always think I'm getting fired. Or somebody says, chris, we need to talk.

No matter who it is, it could be somebody that. It's totally different department that's not even a manager. I'll still think I'm getting fired.

If it's my wife, I'm going to be like, all right, I guess this is it. I'm. We're getting divorced immediately. I get. I'm going to start packing before we start the conversation. That's just me.

I've been traumatized enough by that phrase. So like.

But saying so being clear right away so you reduce that anxiety for the other person is saying what exactly you're talking about saying we as much as possible as opposed to I am upset about this. Starting off with I know that we can figure this out together. Can we talk about this so we can come to a good resolution?

I want us to work together well. And then coming up with ground rules. Coming up with ground rules at the beginning and depending on those situations, it could be really elaborate.

Let's sit down and come up with some ground rules versus just being a very couple of lines. Listen, Claudia, I hope we can speak openly and honestly and feel free if we need to share.

If we need to take a break, I hope we can feel comfortable doing that so it doesn't have to be a really big formal thing. But setting ground rules at the beginning also helps them feel comfortable, helps them feel empowered.

It also puts guardrails on the conversation so that if things do get off track Both of you can take a break. You can say, hey, listen, one of the things I talk about was I don't like yelling. Can we just take a break?

Because it seems like we're getting a little heated here. So doing the ground rules. And then also. Oh, the other thing I would start with is saying thank you. Listen, thanks for agreeing to talk with me.

A lot of times that's so disarming. More so than people realize.

Thanking the other person for choosing to be in the meeting because you're acknowledging that they have free will and autonomy and that's more empowering for. That's more empowering than just telling them we're gonna start this conversation acknowledging they have a choice because they really do.

Everybody has a choice to be in the conversation or not. And I've worked, I'm a licensed therapist as well and I've worked in the past with people court mandated to be in treatment.

And I still stay thinking because they really do have a choice. They have a choice to be there or not.

What I love what you're saying is that we starting from a place of compassion and kindness towards the person and you when sometimes it's difficult, I guess if we like furious with someone or frustrated with someone. But I love how you bringing us to this idea. I want to talk about this. This is what's important to me. Thank you for giving me your time.

I want to be honest with you. I would love you to be honest with me. Is that okay? So I love all of this because it's very much. You have a choice, I have a choice.

We are kind towards each other and we're going to have this conversation. You said this. You mentioned the idea of pausing as well and taking that momentum pause.

Is there anything else that you suggest to do so we can stay focused and also calm during those difficult conversations?

Because again, I think that if there are certain level of emotions coming into play, it's not necessary that we don't want to talk about those emotions. Rather opposite we do want to be vulnerable and share them. But how can we still stay in a place we still showing a respect another person.

Yeah, that's part of the preparation is trying to figure out what are your triggers, what makes you feel upset emotionally and then what are you going to do to keep yourself calm. For some people it's yelling. For some people it's crying.

If the other person starts to get angry or if the other person starts crying or things go off plan. Like we come up with this plan and things go off the plan. And they get upset with that, whatever it is, come up with a plan ahead of time.

What do you need to stay calm? Do you need to rehearse it with somebody, what you're going to say so it sounds natural?

Do you need to practice mindfulness or grounding skills or whatever to stay calm and then using them in there, remembering to use them, sometimes writing it on a piece of paper. What's the goal of the conversation as well as what am I going to do to stay calm? So for me, I like taking a deep breath.

One deep breath helps me stay calm, but also summarizing what the other person said.

If I'm starting to get heated, if I'm starting to get upset and they're talking and they're just venting, I'll take a deep breath and then I'll say, can I just summarize what you said?

And really it's number one, it's shown that I'm listening to them, but also it's buying me time to think about what am I going to do about this because I'm upset and should I take a break or should I continue? So doing that helps me stay calm.

Some people I've worked with, they will have a sharp object, like a little rock or something, and when they feel that anxiety or that they start getting heated, they'll press on that rock and that little thing to push their anxiety or the anger into it. And it helps them just stay focused so they don't show it in their eyes or their body. They can just press on this little object.

So it's whatever works for anybody.

Thank you so much.

So really, what are we saying here is that yes, difficult conversations are bloody hard, but we can handle them with preparation, with care, with a skill to some extent. And in return we can have those stronger relationships. So it is worth of doing that. How can we encourage others to have more difficult conversations?

Because, you know, I could be ready to have that conversation with you and someone might be saying, I don't want to engage with this. So again, in situations when we trying to reach out to that person and have that difficult conversations, how can we encourage that?

That's the biggest question I get is whenever I teach it, I understand these rules. I get that. But what if the other person's not playing by these same set of rules or these using these same skills? And the reality is they're not.

That's why we have to learn the skills. The goal of using these skills isn't to necessarily control the other person. It's using it to control and facilitate the dialogue.

And so a lot of it is teaching and sharing why you're doing what you're doing. Hey, I want to set ground rules so that we both feel safe in this conversation. I don't want it to be upsetting for you.

I want to make sure that we get what we need. What would help you feel comfortable in the conversation? Things like that. Like the more we ask permission to do things. That's why I say, is that.

Okay, are you on board with that? Those things are more about how do we create a dialogue where both of us are engaged in the conversation. And you're right, they won't know.

Especially if you're.

If you listen to the podcast or you read books or even if you take my course or things like that or my newsletter, there's all these tips and strategies I give. You have to assume they don't know that any of those skills.

And so it's about how do you use them to facilitate an open dialogue where they're willing to share with you. And they might say things in a different way than we would like. They may not use that. And that's okay.

But part of that preparation is how do we prepare ourselves to realize that's not going to happen in a calm way? And even better if they do, if they use the same language, if they use the same calm techniques, even better, that makes it 100 times easier.

So again, coming back to that point that you made previously, we need to be realistic that this may fail. But we have tried. If it doesn't fail, then there are all those specific, hopefully positive outcomes that we will gain.

But we might have to be realistic as well. Chris, as you know, on the Happiness Challenge podcast, I love to test out different happiness hacks.

So my question to you is, what challenge there or a task? Could you subscribe to me and my listeners to try? As part of this topic of difficult, challenging conversations.

I challenge you to do this. Next time you are preparing for a difficult conversation. Go rehearse with somebody. Not there's two parts. Go rehearse with somebody.

Go practice what you're going to say. Have them push back if you want them to. Number one, rehearse.

But number two, before you say what you're planning on saying, your script or the nice, thoughtful ways, take one minute and say what you really want. So pretend the other person's there and just say what you really want. Yell at them, vent at them, swear.

But take that minute to really let loose and get out of your system. Essentially say what you really want to say so that then you can practice what you want to say.

I've used that before with other people and it's incredible how light they feel afterwards because like they were actually able to say what they want to say. Like, you're annoying me. You're a jerk. I hate this about you. Why can't you do this? It's just nice to get that off our chest sometimes.

Yeah, it's almost like writing a secret letter to someone, never sending it. But as you said, it's just this idea that we just releasing all of that energy rather than keeping it.

And in the moment, hopefully then will be much more kinder and compassionate towards the person. My final question, because this is the podcast on happiness. Chris, I would love to know what makes you happy.

What makes me happy is spending time eating food. Eating food always makes me happy. Spending time with my family makes me happy.

Spending time with friends, having cookouts, just doing things with friends and family around, eating and hanging out always makes me happy.

Fantastic. Thank you. Where listeners can find out more about you and your work.

Yeah, you can follow my podcast, the Art and Science of Difficult Conversations. We're on all the streaming platforms. We're also on YouTube so you can watch the video of us talking.

We just had an episode this week on how to talk about politics at work, so check that out. You can follow me on LinkedIn. That's where I'm most active, so you can find me Chris Long lmhc.

That's where I usually talk the most and post the most. And then you can always just email me chrisyleadershippotential.com to continue the conversation. And what was the other thing? Oh, my newsletter.

I'm also. I have a weekly newsletter where I just talk about how to master difficult conversations and you can sign up on www.tinyurl.com leadership potential.

Thank you so much, Chris. That was truly insightful and I wish you a wonderful weekend with your family and lots of fun if that's what contributes to your happiness.

Thank you so much again and thank you so much everyone for listening. I see you in the next episode when I'll be summarizing the challenge and trying it out. Thank you everyone.