Article: “Building School Culture Through One-on-One Conversations” By: Matt Pitman
Published: September 9, 2025, on Edutopia
URL: https://www.edutopia.org/article/using-check-ins-support-teachers-g...
Edutopia

Introduction

In “Building School Culture Through One-on-One Conversations,” Matt Pitman highlights a deceptively simple, yet remarkably impactful leadership practice: regular, intentional one-on-one check-ins between school leaders and teaching staff. Unlike performance reviews or crisis interventions, these conversations are informal, connection-focused, and deeply human. Despite the chaos of running a school—managing schedules, parents, and curriculum—a leader who centers these conversations often finds them to be a quietly powerful engine for culture-building.

Why One-on-Ones Matter

Pitman emphasizes that these meetings help teachers feel “seen… heard… valued.” They build trust, surface emerging issues before they escalate, foster new leadership, and cultivate a collaborative, innovative environment—but require no budget or elaborate training, only leader presence and intention.

Structure That Sustains Impact

To make one-on-ones sustainable amid busy calendars, Pitman recommends:

• Frequency: Once or twice per term for each staff member; more frequently for early-career educators or those seeking extra support.

• Length: Keep it brief—20 to 30 minutes max.

• Format: Choose a neutral, relaxed setting (e.g., after-school coffee or a walk-and-talk), avoiding formal office environments and distractions.

• Consistency: Block time early in the term and always reschedule if cancelled to signal that the time matters.

Conversation Starters That Open Doors

Pitman anchors each conversation with three open-ended, coaching-inspired prompts:

1. “How are you, really?”

2. “What’s been a recent win or challenge in your teaching?”

3. “Is there anything you need from me right now?”

These simple questions often invite candid sharing—whether venting or offering brilliant ideas. He sometimes adds a creative prompt: “If you had a magic wand, what’s one thing you’d change about how we’re running things?”—an invitation for feedback and innovation. Notes afterward help with follow-up, further building trust.

Tailoring to Experience

Different needs call for different conversations:

• Early-career teachers may benefit from structured support around lesson planning, classroom management, or parent communication, with an emphasis on building confidence.

• Experienced teachers often surface deeper reflections—strategies, leadership aspirations, or lingering frustrations. These exchanges yield rich insights and can help identify emerging leaders: those who show system awareness, student-focused, and coaching tendencies.

Cultivating School Culture Through Dialogue

Pitman underscores that school culture resides not in formal systems but in how people feel daily—safe, valued, and heard. One-on-ones build psychological safety and signal ongoing, not just reactive, listening. One example: a teacher once shared in a one-on-one that staff meetings felt rushed and unclear. That insight led to restructuring meetings—fewer agenda items and more collaboration time—resulting in marked engagement improvements.

These conversations are not about management—they’re about connection. Authentic listening fosters presence, willingness to collaborate, and innovation.

Caveats and Commitments

Pitman cautions that one-on-ones aren’t a cure-all. If they’re inconsistent, cursory, or inauthentic, staff will sense it. The practice succeeds only with curiosity, presence, and reliable follow-up—not perfect scripting.

Reflection for Leaders

As you plan for the coming year, Pitman invites reflection:

• Who on my team needs to be heard right now?

• What might shift if I truly made the time to listen?

You may be surprised—not just by what opens up in others, but what opens up in you. 

Summary Table

This summary offers educators a clear framework and rationale for integrating one-on-one conversations into leadership practice—an accessible, relationship-based tool for elevating school culture and teacher well-being.