4 Ways to Know When a Hard Conversation is Actually Going Well

"I tried being truthful about what was on my mind and it blew up in my face."

That's what a client recently said to me as we were reflecting on his Conversational Intelligence practice. Of course, I got curious. “What do you mean? Tell me more.”

So he did. He started explaining the situation and what had happened. And as he unpacked the story, something became clear: what had unfolded wasn't that things actually blew up in his face.

Yes, it was uncomfortable. Yes, there was a period where he felt disconnected from the person he was speaking with and needed space. And yes, they figured things out moving forward. They went through the process of repair.

Did the conversation go perfectly? No. But these kinds of conversations rarely go perfectly.

The Myth of the Perfect Difficult Conversation

Here's something most people don't realize: when a hard conversation appears to go perfectly, it's often because there are things that aren't being said that need to be discussed. Someone's saying one thing and thinking another. They're acting like everything's okay while not actually thinking that.

It's one of the biggest misconceptions about difficult conversations—that having a disagreement or struggling to navigate something challenging means it "blew up in your face." What it actually means is that you're dealing with things that need to be dealt with.

Things that avoiding was getting you nowhere and, in fact, making worse.

4 Ways to Know When a Hard Conversation Is Actually Going Well

So how do you tell when a difficult conversation is on track, even when it feels messy and uncomfortable? Here are three key indicators:

You're Learning Something From the Other Person

You know it's going well if you're willing to be curious, listen, and strive to understand where the other person is coming from. That's a sign it's working.

This doesn't mean you have to like what they're saying. It doesn't mean you have to agree with what they're saying. It doesn't mean that what they're saying feels good to hear. All of those reactions are common in hard conversations that are actually going well.

But if you're approaching it with genuine curiosity rather than defensiveness, that's a good sign.

The Other Person Is Being Vulnerable With You

Another sign that things are progressing well is when the other person starts sharing openly about their thoughts, feelings, fears, assumptions, and concerns.

These can be really hard things to hear and equally hard to say. But if we don't hear them, we can't address them. If we can't listen to connect with what other people are saying, we can't show them that we genuinely care—because we don't actually understand what it means to demonstrate that to them.

So, when the other person is being vulnerable, that’s another sign things are going well.

Regulate with a Pause

You know a conversation is going well when you can actively and effectively gut-check some of your impulses to fight, defend, argue, attack, or shut down.

That's not to say that hitting the pause button is wrong. In fact, that's another sign that a hard conversation is going well—when things are getting heated or escalating, you can agree to take a break and come back to it.

In most instances, there's no reason to keep pushing through. You don't need to soldier through a hard conversation because the majority of the time, there's nothing urgent about it. Most of the time, you're not making a critical life-or-death decision that needs to be resolved then and there.

You Can Recognize and Repair Your Missteps

Here's the thing: you're not going to show up perfectly in difficult conversations. You might lose it at one point. You might say something you didn't mean, or say something in a way you didn't intend. You might react defensively.

And here's how you know it's going well: you actually recognize the disconnect between your intentions and your impact, and you engage in what Brene Brown calls "healthy shame" to acknowledge and repair.

It sounds like: "Hey, I'm sorry I said that in a way that felt dismissive and hurtful to you. That is not at all what I meant to do. I can see how it felt that way to you. I was really distracted by other things. In the future, I need to make sure I’m able to be fully present when we are going to have a hard conversation like this."

Everyone makes conversational mistakes. Especially when discussing a sensitive topic where emotions run high. Recognizing and repairing missteps is a sign things are going well.

From Rupture to Repair: The Real Victory

For my client, things didn't actually blow up in his face. It felt that way, but what really happened was an opening to navigate what relationship experts call the rupture to repair cycle.

This is huge for someone who is conflict avoidant. It’s a major milestone for someone who constantly needs to be the people pleaser, the peacekeeper, the one who's there to make other people happy and support others. To actually give voice to a concern, a need, and a boundary—and to do it in a way where the relationship doesn't end but actually gets stronger.

That's not blowing up in your face. That's opening. It's creating space to strengthen a relationship.

Why Repair Makes Us Stronger

In college, I owned an old Subaru with a manual transmission. The clutch needed to be replaced, which was an expensive repair that involved taking the engine apart and putting it back together. I lamented the cost. Yet, as I drove the car away from the mechanic, I was pleasantly surprised that the car felt safer in ways I hadn’t expected from the repairs. 

That's what happens in relationships when we navigate difficult conversations well. The repair doesn't just restore what was there before—it creates something stronger. Going through repair fosters psychological safety, because it shows us our relationship can endure a misunderstanding or conflict. We learn we don’t have to be perfect to be accepted and so we’re willing to take the risk of being more truthful about our needs and boundaries.

Redefining Success in Difficult Conversations

The next time you find yourself in a challenging conversation, remember: success isn't measured by comfort or agreement. It's measured by curiosity, vulnerability, and the willingness to repair when things go sideways.

If you walked away learning something about the other person, if they felt safe enough to share what was really on their mind, and if you were able to acknowledge your own missteps—that conversation didn't blow up in your face.

It opened something up. And that opening is exactly where real connection begins.