Bridging Differences through Conversation

On a Wednesday afternoon in February, Yale staff members practiced building connections at two Cultivating Conversation workshops. Many participants walked in as strangers or colleagues who rarely interact—and walked out feeling more connected and better equipped to navigate meaningful conversations at work and beyond.

Led by Becca Kearl and Annie Caplan of Living Room Conversations, the sessions offered dialogue practice as well as a reminder of how powerful it can be when we slow down, listen closely, and approach one another with curiosity. Drawing from the insights Kearl and Caplan shared, here are some of the key practices that can help all of us have better, more connected conversations.

Start with agreements, not rules

Begin a conversation with shared agreements: simple, mutual commitments such as listening with curiosity, speaking from personal experience, and respecting each other’s time. These aren’t rules to enforce but expectations everyone actively agrees to uphold. They help create an environment in which people feel comfortable sharing honestly.

Stick to a structure

Structured formats—like giving each person an equal amount of speaking time—help neutralize power dynamics and keep a conversation moving forward. An agreed-upon structure can help people engage with one another as equals without getting caught up in titles and roles. This is especially valuable in workplaces, where hierarchy can unintentionally discourage some voices.

Build from common ground

Before diving into harder topics, Caplan recommends starting with questions that help people find early points of connection such as favorite music, food, the weather, or anything accessible. This isn’t small talk for its own sake; it’s how trust is built. When people see one another as fully human, they’re more willing to explore differences constructively.

Shift from judgment to curiosity

As Kearl notes, our brains are wired for snap judgments. The goal isn’t to stop judging but to notice when it happens and pivot to curiosity instead. Questions like “What resonated with you about that?”, “What does this look like in your life?” or “Have you had an experience that shaped your view?” can help move conversations from debate to understanding.

Center stories, not opinions

Both leaders emphasize that meaningful conversations focus on stories, not arguments.
Personal experience provides richer context, reduces defensiveness, and opens space for empathy. When people share the “why” behind what they believe, conversations and deepen through understanding.

Small connection sparks a bigger cascade

Kearl describes something researchers call a connection cascade: when someone has one positive experience connecting across differences, they’re far more likely to do it again. This ripple effect can shift a team or even an entire community. In the workplace, that means a single positive conversation can influence how a person collaborates, listens, and shows up for others.

Conversation takes practice, but it’s worth it

Caplan acknowledges that conversation isn’t always easy or intuitive. People can become  discouraged, tired, or overwhelmed. But avoiding dialogue only deepens disconnection.
The good news is that most people genuinely want to talk. They want to understand and be understood. And practicing these skills, even in small ways, can shift a culture toward one that values connection over polarization.