The Simple Trick to Break Free from Circular Conversations

One of the things I love most (and yes, sometimes groan about) in my work as a leadership coach and facilitator is how quickly the root of a conflict reveals itself when you really listen.

Not long ago, I was brought in to mediate a conversation between two employees. Within minutes, it became crystal clear why they kept running into the same wall over and over again: they weren’t talking with each other—they were talking to each other.

And that subtle shift in prepositions? It makes all the difference.

The Transaction Trap

When we talk to someone, it’s transactional. It's like dictating directives to Siri. We don’t expect comprehension, just compliance. 

“Siri, text my mom…” 

Transactional conversations have a role in the workplace. It’s the stuff of dates, deadlines, and directions.“Submit your content by Friday.”“Here’s the SOP.”

These aren’t inherently bad exchanges—they’re necessary! But when this mode of communication becomes our default we miss opportunities for connection and problem-solving. 

That was exactly what was happening between the two co-workers. One would share their thoughts and needs, and the other would jump straight into a rehearsed defense. No pause. No reflection. No effort to understand. Just auto-reply mode, as if on a loop.

It was no wonder they weren’t getting anywhere.

Talking With Builds Bridges

When we shift into talking with someone, we enter a different space—one of shared presence and possibility. This is where true conversation happens, not just a mindless transaction. This is where there’s room to explore, reflect, and co-create.

That means slowing down. Listening to connect, not judge, confirm or respond. It means using practices like:

• Reflective listening:“What I’m hearing you say is… Is that right?”

• Curious inquiry:“Tell me more about that.”“What does that mean to you?”“Can you give me an example?”

These are small but mighty tools that turn defensiveness into dialogue. They open the door to understanding how someone else is experiencing the situation—not just what they’re doing, but why they’re doing it.

Getting to the Root, Not Just the Rule

Let’s say there’s an issue with how someone is following a process. You could say, “This is the procedure. Do it this way.” That’s talking to them.

Or, you could approach it with curiosity:“What’s been your approach so far?”“What’s making it hard to follow the process outlined here?”“What ideas do you have for making this work better?”

And you say all of this with genuine curiosity-otherwise your tone will betray you and such questions will feel like masquerading judgments. 

Approaching conversations with genuine curiosity and a desire to understand are at the heart of talking with someone. And in that shared space, you’re more likely to uncover what’s really getting in the way—and find a solution together.

Embracing the Messy Middle

Talking with someone takes more time. It’s not as tidy. It doesn’t follow a precise script. But it’s in the mess that real transformation and growth happens.

When leaders and team members talk with one another, they build trust, connection, and shared ownership. And that’s what strengthens your culture and accelerates meaningful change.

So next time you feel the urge to “just get to the point,” pause and ask yourself:

Am I talking to this person, or with them?

The answer might just shift everything.