When Difficult Conversations Heal. And When They Don’t

Over the years, I’ve learned that difficult conversations are unavoidable, whether in leadership, families, or life. What is avoidable is the damage they cause when we choose defensiveness over listening, or comfort over courage.

Lately, I’ve been reflecting on several experiences, some deeply personal, some professional, that taught me just how powerful (and rewarding) scary conversations can be when they’re handled with care.

A Difficult Conversation That Worked

Years ago, I participated in a six-month intensive personal and professional development program. During one group call, our tribe leader made an offhand comment about me, something along the lines of, “Lori doesn’t need help with organization. She’s got it all figured out.”

Whether that was her exact wording or not, the impact was immediate. It stung. It felt dismissive. And at that time in my life, my default response to feeling hurt would have been to quietly disengage. You hurt me? You lose me.

Instead, I did something different. As soon as the call ended, I picked up the phone and called her.

I asked a simple question: “Can you help me understand what you meant by that comment?”

Her response changed everything.

She didn’t defend herself. She didn’t explain it away. She didn’t minimize how it landed. She apologized immediately, acknowledged that it came out wrong, and shared that what she meant was admiration and respect.

The tension dissolved, not because the comment never happened, but because it was met with listening and humility. Nearly a decade later, we still have a strong relationship.

That conversation worked because the person with more authority listened without a plan to respond and chose repair over protection.

When Scary Conversations Lead to Repair

I’ve seen this play out in other areas of life, too.

Years ago, my husband was speaking with a couple who had no contact with their adult son and had never met their granddaughter. They explained it was due to differences in opinions and values around parenting.

My husband gently responded, “It sounds like you value your opinion more than your relationship.”

Mic drop.

The words landed. Over time, that couple reflected, softened, and ultimately repaired their relationship with their son.

In another moment, I mailed my parents a copy of Being Mortal by Atul Gawande, a book about end-of-life planning, wishes, and dignity. Sending it felt awkward, vulnerable, and scary. But they both read it, appreciated it, and thanked me for starting a conversation that mattered.

These moments remind me that scary conversations, when approached with honesty and care, can be incredibly rewarding.

My husband often jokes, “If you’re scared, say you’re scared.” The deeper meaning? Do it anyway.

When Conversations Don’t Heal

Not all difficult conversations land this way.

I’ve also witnessed situations where feedback was met with defensiveness instead of curiosity or humility; where lived experiences were reframed as accusations; where excuses, justifications, and explanations replaced accountability; and where the goal became resolution without repair.

In those moments, power dynamics matter. Intent begins to outweigh impact. And the person with less power often walks away feeling responsible for managing the relationship by tempering expectations, shrinking, or adapting rather than feeling heard.

That isn’t conflict resolution. It’s conflict containment.

What I’ve Learned About Leadership and Listening

The difference between conversations that heal and those that harm isn’t communication skill, it’s posture.

• Listening is not waiting to respond. It’s suspending your need to defend yourself.
• Impact matters more than intent. Especially across power lines.
• Apologies don’t assign blame; they acknowledge experience.
• Avoidance and separation don’t resolve conflict; they simply move the burden.
• When someone offers feedback with vulnerability, how you receive it determines whether they’ll ever do it again.

Why I’ll Keep Leaning In

As someone who cares deeply about employee morale, culture, and human experience, I will continue to raise awareness around these ideas at work and beyond.

I want people to feel safe, seen, valued, fulfilled, and empowered.

I want that for myself. I want it for others.

Whether I’m writing, hosting a dinner party, facilitating a training, navigating leadership conversations, or working in marketing or communications, this value remains the same.

Scary conversations, when handled with care, have the power to build trust, deepen relationships, and create real change.

And that’s a risk worth taking.

©2026 Lori Ann King