Engaging in Difficult Conversations
Tim Ferriss once said, "A person's success in life can usually be measured by the number of uncomfortable conversations he or she is willing to have." In schools, the fast pace of the day, combined with full schedules and the natural stressors of the work, can create fractures in relationships, without much time built in to repair them. These moments are often left unaddressed, either because people avoid conflict altogether or fear making things worse. And yet, it’s exactly these conversations that tend to matter most.
Whether it’s a colleague disagreement, a concern about classroom practice, or a sensitive conversation with a student or parent, these moments test our ability to stay grounded and relational. At Collaborative School Culture, we believe that engaging in difficult conversations is not just a leadership skill—it’s a core relational and conflict resolution skill that must be modeled, taught, and practiced across the entire school community.
Difficult Conversations
Engaging in difficult conversations is a necessary part of building a thriving school culture, especially at a time in schools when employee engagement is low. Whether it’s providing feedback, navigating miscommunication, addressing discipline with families, or surfacing tension among colleagues, these moments have the power to fracture—or strengthen—relationships. The key lies in how we approach them.
School leaders and educators often avoid difficult conversations for fear of damaging relationships or making things worse, or just out of fear. But avoidance rarely solves the issue—it just delays the rupture. Instead, we encourage a relational approach that blends clarity, empathy, and accountability. When done well, difficult conversations can build trust, promote shared ownership, and lay the groundwork for stronger partnerships across the school community.
At Collaborative School Culture, our training goes beyond tips and tricks. We help school teams develop the internal regulation, language, and relational strategies that lead to productive, values-aligned conversations.
Why Difficult Conversations Are Hard (Especially in Schools)
We’re often told to stay calm, professional, and open-minded during conflict. But no one tells us or shows us how. Who is modeling these skills these days? When something’s at stake, our stress response can take over, leading to reactivity, shutdown, or overcorrection. And because schools are inherently relational, with overlapping power dynamics and ongoing contact, unresolved issues fester.
In our Curbside Conversations training, we focus on:
Regulating yourself first—using bottom-up brain strategies to get grounded before engaging. These include movement, breath work, sensory regulation, and visualization to downshift the nervous system.
Reflecting on what’s happening, what do you suspect are the underlying thoughts and feelings of the other person? How about you?
Knowing your purpose—are you seeking clarity, repair, or accountability?
Recognizing when you’ve moved outside of the "With Box"—defaulting to too much control or too much accommodation.
What Tools Support These Conversations?
We offer a few key tools to make difficult conversations more constructive:
The Compass of Shame: When someone feels something has changed relationally and is no longer positive, or if they feel exposed, blamed, or judged, their behavior often shifts into one of four shame responses: withdrawal, avoidance, attack self, or attack other. Understanding this helps people normalize their response, reframe someone else’s response, and avoid escalating a conversation.
The Engagement Window: This tool helps us recognize how we engage others. When we are in the "With Box," we’re offering both high accountability and high support—we’re doing things with people, not to them or for them. This provides a north star for navigating relationships and moving through conflict to a better agreement.
Affective Statements: These brief, personal expressions of emotion help communicate how someone’s behavior impacted you, without blame or shame. For example: "I’m feeling overwhelmed. Could you help with planning the field trip?" Affective statements build connection and foster emotional literacy in both adults and students.
Restorative Questions: Rather than leading with reprimands or assumptions, we use structured, curiosity-driven questions to understand impact and plan forward. Examples include:
What happened, and what were you thinking at the time?
Who might have been affected?
What do you need to move forward?
Curbside Conversations: These brief, relational interactions offer an opportunity to quickly check in and express emotions in a way that feels informal but still intentional.
We provide tangible tools to accompany these concepts that help educators prepare or debrief these moments by clarifying purpose, grounding themselves, and considering tone, timing, and relational impact.
Why This Matters for School Culture
The way adults communicate shapes the culture students experience. When conflict is avoided or when conversations are handled harshly, trust breaks down. But when adults model regulated, respectful, and direct communication—even when it's hard—students learn that relationships can withstand tension and repair.
Staff also deserve environments where feedback is timely, consistent, and rooted in values. Difficult conversations about instruction, collaboration, or norms don’t need to feel threatening. They can be opportunities for reflection, growth, and recommitment to shared goals when handled with skill and intention.
Importantly, research has shown that employee engagement is deeply connected to trust in leadership, clarity of feedback, and a sense of voice and agency at work. In educational settings, where stress levels are high and retention is low, creating a culture that supports skillful communication and relational repair is more than a nicety—it’s a necessity.
Bringing In Restorative Practices
Restorative Practices aren’t just for student conflict. They’re a framework for adult relationships, too. When we approach staff and families with curiosity rather than judgment—and when we use tools like affective statements, neutral language, and fair process decision-making—we build cultures of dignity and voice.
Fair process reminds us: people are more likely to accept decisions—even ones they don’t prefer—when they’ve had a voice in the process, the rationale was clearly explained, and expectations were followed through. These same principles apply to difficult conversations.
Training That Builds Capacity
At Collaborative School Culture, we help educators build muscle for these conversations. Our sessions:
Use real scenarios from your context
Model restorative language and strategies
Provide reflection tools for before, during, and after
Help teams address conflicts more easily and naturally, especially when things are small, while also having the tools and skills to manage the big things
We also help leaders create systems for accountability, support, and repair that don’t rely on personal charisma alone. Because culture should never depend on one person—it should be embedded in the fabric of how your team communicates.
A School’s Culture Can Be Measured By The Number of Uncomfortable Conversations Its Members Are Willing to Have
The quality of a school’s culture isn’t just visible in its vision statement or student handbook—it’s visible in how people intentionally build relationships as well as how they talk to one another when things are hard.
Difficult conversations aren’t a problem to avoid. They have a capacity to build. And when schools invest in that capacity—through Restorative Practices, training, and a shared language—they create environments where trust can grow, even in moments of tension.
Contact the Collaborative School Culture team and let us help your team get there. Together, we can strengthen the way your staff engages with each other, with students, and with families—one conversation at a time.