How to Have Difficult Conversations That Strengthen Relationships

There’s a moment—sometimes loud, often quiet—when you know a difficult conversation is coming. It’s the tightening in your chest when an employee misses the mark again. It’s the silence after a friend’s comment that cuts too deep. It’s the long pause in a meeting when everyone realizes the unspoken tension can’t stay unspoken any longer. As a trusted colleague of mine always says, “the things that 'go without saying,' should always be said.”

And here’s the truth most people don’t say out loud: Difficult conversations aren’t just necessary—they’re a litmus test of our leadership, our courage, and our relationships. 

But what if I told you that these moments, the ones we often dread, can actually deepen trust, strengthen teams, and grow connections when handled with care and intention?

Let’s talk about how.

The Story We Tell Ourselves

It was a Thursday night when I found myself standing outside the walk-in cooler, staring down at the tile floor, like it might offer answers. One of my best line cooks, Jamal, had just walked off the line mid-service. No warning. No conversation. He just a slammed pan and vanished.

I was angry. Disappointed. And if I’m honest, a little hurt. Jamal had been with us for over a year. He was solid. Reliable. Quiet, yet focused. The kind of person you don’t worry about—until you do.

I knew I had to talk to him. But what would I say? And more importantly, how would I say it without making things worse?

That internal dialogue—that swirl of emotion and hesitation—is where most difficult conversations stall. We begin crafting a story: They don’t respect me. I've done so much to support them. They’re impossible to talk to. This won’t end well.

But here's the catch: The story we tell ourselves before the conversation determines how we show up during it.

Why We Avoid Hard Talks

You’re not avoiding the person. You’re avoiding the discomfort. The confrontation. The possibility of being misunderstood. And you’re not alone. Most leaders, friends, and partners avoid difficult conversations because:

• We fear conflict. We associate conflict with damage, not growth.

• We worry about saying the wrong thing. We think our words have to be perfect.

• We assume intent. We believe we already know why someone did what they did.

The result? We wait. We delay. We bury the issue. And in doing so, we often damage the very relationships we’re trying to protect.

Reframing the Goal: It’s Not About Being Right

Here’s the shift: Difficult conversations aren’t about being right. They’re about being real.

They’re about choosing honesty over comfort, clarity over avoidance, connection over control.

When you enter a tough conversation with the goal of “winning” or “fixing” someone, you lose the opportunity to actually understand them. But when you show up with curiosity and care, something powerful happens—you create space for truth. And truth builds trust.

6 Steps to Navigate Difficult Conversations That Build, Not Break

Let’s move from theory to tactics. Here’s a proven framework I use with clients—and in my own leadership work—to turn challenging conversations into relationship-deepening moments:

1. Check Your Intentions

Ask yourself: What do I really want from this conversation? If your answer includes “to make them feel bad” or “to prove I’m right,” you’re not ready.

Go in with a goal of clarity, connection, and progress. This isn’t about blame—it’s about understanding and moving forward.

• “I want to better understand what happened and figure out how we move forward together.”

2. Ground Yourself Emotionally

If you’re charged, frustrated, or emotionally raw—pause. Take a beat. Regulate your nervous system before walking in. Deep breaths, a short walk, or a five-minute journaling session can work wonders.

• You don’t need to be emotionless. You just need to be in control of your delivery.

3. Start With Curiosity, Not Accusation

Lead with questions, not conclusions. Give the other person room to tell their story.

“Hey Jamal, I noticed you left the line during service. I’d really like to understand what happened. Can you help me make sense of it?”

• This approach invites dialogue. It signals that you’re not here to attack—you’re here to understand.

4. Name the Impact, Not Just the Behavior

It’s one thing to point out what happened. It’s another to share how it affected you or the team.

“When you left the line, it really threw the kitchen off. Service slowed down, and people were confused. I want to figure out how we prevent that in the future.”

• This builds empathy. It humanizes the conversation.

5. Pause for Their Perspective

Here’s where most leaders blow past the opportunity for real connection: They don’t actually listen.

Let them talk. Resist the urge to interrupt or defend. Validate what you can. You don’t have to agree to acknowledge.

• “Thanks for sharing that—I didn’t know you were feeling that way. I can see how that would be tough.”

6. Co-Create the Path Forward

The goal isn’t to assign punishment. The goal is to build a better future—together.

• “What would help you feel supported if something like this comes up again?” 

• “Let’s come up with a plan that works for both of us.”

What Happens When You Get It Right

Back to Jamal.

I took a breath. Walked into the break room. Asked him if he was okay.

His eyes welled up. “I’m not,” he said. “My mom’s sick. I’ve been trying to hold it together, but that night, I just broke.”

And there it was—the story I hadn’t known. The context that changed everything.

We talked. Not just about work, but about life. I gave him space to step away and offered support for when he returned. He came back a week later. Stronger. More committed. And we had a deeper relationship than ever before.

That conversation could’ve been a fracture. Instead, it was a foundation.

Pro Tips to Keep in Your Back Pocket

• Tone > Text. Whenever possible, have hard conversations in person or over video. Text and email strip nuance and leave too much room for misinterpretation.

• Timing matters. Don’t bring up a major issue at the end of a long shift or during a stressful meeting.

• Own your part. Even if it’s just how you approached the situation. Accountability invites reciprocity.

• Practice first. If the stakes are high, role-play with a coach or trusted peer.

• Follow up. One conversation doesn’t fix everything. Check in. Keep the door open.

The Courage to Be Clear

There’s a kind of resolute leadership that happens when we choose to face discomfort instead of flee from it. When we speak from the heart and hold the line. When we decide that relationships matter more than being right—and that honesty is a form of respect.

You won’t always say the perfect thing. You might fumble. You’ll learn. And that’s the point. The goal isn’t perfection. It’s presence.

Because the leaders who have the greatest impact aren’t the ones who avoid hard conversations. They’re the ones who lean into them with empathy, integrity, and the belief that people—even in conflict—are worth the effort.

And that kind of leadership? It doesn’t just change outcomes - it changes people!