What working across education has taught me about listening

When we hear the word listen, we often think about hearing what someone is saying.

But in education and leadership, listening asks more of us. It means trying to understand the person sharing those words and being willing to adapt based on what we learn.

I’ve spent my career as a classroom teacher, school counselor, school and district leader, nonprofit CEO, and EdTech leader. Across those roles, the questions have changed. The need to understand people has remained.

As a teacher, I could hear a student’s answer and determine whether it was correct. But was I also learning something about how that student thought? Their confidence? Where they needed support? And did I adjust what I did next?

As a counselor, active listening was foundational. My responsibility was to create space, ask thoughtful questions, and understand what someone was sharing before jumping in with advice. Sometimes that meant exploring what was behind the words and checking whether I had understood.

One high school student’s experience illustrates why that matters.

The student had been removed from a classroom for acting out. That behavior was the reason for the conversation. But as we listened and worked through the layers, a different concern emerged.

The student had tested into the class but didn’t feel confident in their ability. They didn’t believe they belonged there. That insecurity was showing up in their behavior.

Understanding that changed how we understood the situation. Alongside addressing what had happened in the classroom, we needed to help the student understand why they were there and build confidence that they belonged.

Listening helped us see a need we could have missed if we had stopped at the behavior.

Stephen R. Covey captured an important part of this in his fifth habit:

“Seek first to understand, then to be understood.”

That takes practice, especially when we’re busy, responsible for making decisions, or convinced we already know what’s happening.

As leaders, we can hear a team member’s concern and immediately start forming a response. But have we understood what they need? Do we know what motivates them, what they’re worried about, or what might be getting in the way?

Research offers a useful perspective here. In a 2021 study published in Frontiers in Psychology, researchers interviewed 41 bank employees about experiences of feeling heard or unheard. Their accounts suggested that attention during a conversation was sometimes insufficient. Feeling heard also depended on a response that met the person’s needs—and, in some situations, follow-through afterward.

That finding connects with my experience across education. A conversation can help someone feel understood. It can also reveal something we need to change.

Leading an education association meant understanding what members needed and how those needs differed across communities. Working in EdTech meant listening to district leaders and educators, understanding the realities behind their feedback, and helping that insight inform decisions.

Now, through Heffner & Co., listening is where the work begins. Before building a strategy, we need to understand the people, the challenge, and what matters.

A few questions help me stay focused:

What am I learning about this person beyond the words they’re sharing?

What assumptions am I bringing into the conversation?

Have I checked that I understand?

What should I reconsider or do differently because of what I heard?

Across schools, education nonprofits, and EdTech, those questions help keep us connected to the purpose of our work: supporting students so they are prepared to succeed.

How will this help students succeed? Sometimes the next step toward answering that question is making space to understand someone more fully.

What has someone helped you understand because you took the time to listen?