Episode #446 – What Conversation Do You Need to Have?

This is episode 446 of the Brilliant Balance podcast. What conversation do you need to have? Because I am willing to bet that there is one. There is a conversation somewhere in your life with somebody who matters to you that, deep down, you know you should be having—and you are not having it.

Maybe you’re sitting here today and you know exactly what it is, right? It surfaced for you as soon as I said that. Or maybe you’ve gotten so good at not thinking about it that you’ve stopped even calling it a conversation.

You’ve recategorized it. It’s just a thing you live with now. It doesn’t even feel like there’s a conversation to be had because it would be pointless. There’s that low-grade hum of discontent, and you’ve decided this is the price of admission for the relationship you’re in, or this job, or this season. I really want to challenge that today—that settling, that giving up, that resigning yourself to something being less than it could be.

It goes back to a time when I asked for something at work while I was in my corporate job at Procter & Gamble. The thing I asked for essentially didn’t exist in my corner of the company at the time. I was also 10 months into maternity leave when I did it. I’m telling the full story over on Substack today, and you can go there to read it. But what I want you to know right now is this: I walked into that room absolutely convinced the answer would be no—and they said yes. It changed the entire trajectory of the next decade of my career.

From years of watching women change their lives—and watching others avoid these conversations—as well as from my own experience, I genuinely believe that everything you want is on the other side of a courageous conversation.

Not a perfect one. Not a perfectly scripted, rehearsed, “I know exactly what I’m going to say” conversation. A courageous one. Not a comfortable one either—not a “this is easy, let’s grab coffee” kind of conversation. A truly courageous one.

So what is a courageous conversation?

You might have your own definition, but I want to calibrate ours. I think it’s a conversation where something real is at stake. You have a truth to tell. Something you need to explain, ask for, or ask about. And something matters because of it.

Maybe it’s your comfort—you won’t feel as comfortable afterward. Maybe it’s the relationship—you think it might shift or change. Maybe it’s your job, or someone’s opinion of you. But there’s something about it that makes the stakes feel real.

Because of that, we avoid it.

We tell ourselves little lies: “It’s not the right time.” “What if this ruins things?” “What if it makes it worse?” “I’ll get to it eventually.” And eventually becomes never.

By “we,” I mean me too. Historically, this has been a pattern in more conversations than I’d like to admit. We put off important conversations because they’re scary.

There’s a book you might have read called Crucial Conversations by Kerry Patterson and others. One of the points they make is that at the heart of almost every chronic problem in our relationships or organizations is a conversation we’re either not having or not having well.

Not occasional friction—but chronic problems. The things that have been sitting there for months or even years, festering. The things you’ve decided to live with. There’s almost always a conversation underneath that, if we had the courage to have it, could lead to a different outcome.

But we don’t.

Why?

One reason is what I call anticipatory emotions. We feel all kinds of emotions just thinking about the conversation, so we avoid it entirely. We opt out before we even begin because the discomfort feels so real—almost as if the conversation has already happened and gone badly.

We rehearse the worst-case scenario. They’ll get defensive. I’ll get flustered. It’ll become a whole thing. We write entire mental screenplays of conversations that never happen.

So we start to believe the conversation itself is the problem, when really it’s the story we’re telling ourselves about it.

Brené Brown talks about this idea—saying, “The story I’m telling myself is…” That phrase reminds us that our interpretation might not be reality. For example: “The story I’m telling myself is that you’re mad at me because you left my text on read.”

We don’t actually know that. We’re assigning meaning based on our fears.

The second reason we avoid these conversations is what I call the “crystal ball problem.” We assume we already know how the other person will respond. We say, “I’m not even going to ask—I already know what they’ll say.”

But we don’t know. We’re guessing—and usually guessing the worst to protect ourselves.

In doing that, we eliminate the possibility that the conversation could go differently.

From my experience, real conversations almost never go the way you imagine—and they’re usually better than you expected. Could they go badly? Of course. That’s why it takes courage. But most of the time, they go better than your fear predicts.

Another reason we avoid these conversations is that we haven’t clearly connected what we want with the conversation standing between us and getting it. When you stay focused on the desired outcome, it becomes easier to move through the discomfort.

Let’s look at a few examples.

If you want more flexibility at work—leaving early for your child’s activities, skipping unnecessary meetings, or working from home—that outcome is on the other side of a conversation with your manager. Not a hint. Not a hope. A clear, specific conversation where you explain what you want, how you’ll manage it, and why it will work.

If you want a healthier relationship with your mother—one where you feel seen instead of managed—that’s on the other side of a conversation where you gently but clearly explain how a specific behavior affects you.

If you want a more balanced friendship, that’s on the other side of saying, “I feel like I’m always the one reaching out. Can we talk about that?”

If you want your teenager to open up, that often starts with you initiating the conversation in a way that feels safe and curious, rather than waiting for them.

If you want a colleague or team member to stop doing something that’s bothering you, that’s on the other side of a direct, honest, compassionate conversation.

The pattern is always the same: there’s something you want, and there’s a conversation standing between you and that thing.

We tell ourselves that conversation is impossible or pointless—but we don’t actually know.

So here’s the challenge: go have one.

When you do, a few things happen.

First, you feel more confident. Not before the conversation—after it. Courage produces confidence, not the other way around.

Second, you’ll want to have more of these conversations. Once you experience the results, something shifts.

Third, your life actually gets better. Because the premise is true: everything you want is on the other side of a courageous conversation.

When you think about people whose lives seem to work—who have strong relationships and navigate challenges well—it’s likely they’ve learned how to have the conversations others avoid.

And that can be you.

Knowing you need to have these conversations isn’t the same as actually having them. That gap is real. That’s why I created the coaching circle—to help bridge that gap and turn insight into action.

But for today, don’t start with your hardest conversation. Not the 11-out-of-10 one. Start with a four out of ten. Something a little uncomfortable, but manageable.

Have that conversation this week. See what happens.

And then tell me about it.

Until next time, let’s be brilliant.