This article appeared as "Talk Tactics" in the Winter 2026 issue of Independent School.
One morning during drop-off, a head of school named Sarah noticed a teacher arriving late and parking for the day in a coveted 15-minute spot. When Sarah confronted the faculty member, he shot back with a reply about previously unmentioned physical challenges (bad knees), an ailing live-in mother-in-law, and the need to preserve his expensive footwear. The teacher later brought up this exchange in a faculty meeting, and colleagues shared a litany of similar, seemingly unfair accusations from Sarah. From holding faculty to policy to redirecting energy toward streamlining systems, Sarah was under scrutiny. She began to question whether her leadership style was truly serving her school.
Sarah had always prided herself on being a strong leader. She had extensive administrative and classroom experience. She had coached others. She thought she had seen every facet of the independent school experience. But something wasn’t right. She was determined to gain some clarity and grow and sought out leadership coaching. We worked together last summer.
From one-on-one sessions with regular clients to school retreats, I’ve worked with leaders like Sarah from all kinds of schools—faith-based, single gender, coed, boarding, and day, from pre-K to 12th grade. We talk about change management, strategic planning, best practices for a board of trustees, faculty morale, or why a team isn’t working well together. So many of the leaders I’ve coached have just needed time and space away from the daily business of running a school to reflect on issues that tend to build up over time.
The conversations that school leaders are required to have as part of their job carry an enormous amount of weight, and their words and actions can have a huge impact. It may sound simple, but working with a leadership coach who asks open-ended questions, listens, and reflects back what they’ve heard can help heads and other school leaders minimize the emotional tax of difficult conversations.
Using a simple coaching framework to handle conversations under pressure can help leaders at every level build connections, lower the temperature of contentious exchanges, and better understand relational dynamics.
Dynamics at Play
Texting a teacher to ask why they aren’t in school yet, speaking with parents or teachers about an “unfair” decision, being taken to task by a board member, or being told in April that their contract won’t be renewed for next year but they need to stay upbeat “for the students”—school leaders are confronted with many planned and unplanned conversations like these every day. And they’re expected to do and say the right thing and be “media ready” at all times.
The conversations are coming from all directions. In many school communities, people—families, staff, alumni, and especially students—feel very deeply connected to the school. That’s always a good thing, but there’s a challenging dynamic at play when people’s deepest emotions are involved.
It’s important that school leaders identify and understand these dynamics so that they recognize that it’s not a reflection of their leadership; it’s how people elevate—and sometimes contort—the role of school leaders. I reminded Sarah that, regardless of the circumstances, she has to be prepared to interpret each and every exchange for multiple complexities.
Three Steps
Schools rely on their leaders to be everything for them. It’s a tall order, but there are three relationship-engagement steps that all leaders—from administrators to heads of school—can take to build trust, identify key points for conversation, and reduce the level of emotion in exchanges with any member of the school community.
Ask. There are many scenarios in which asking questions combined with a little patience can go a long way. For example, heads often hear about problems through the grapevine. They may hear that an administrator is having trouble dealing with the faculty. Rather than jumping to conclusions and assuming the report is true, a head should dig deeper, asking the administrator how things are going rather than starting a conversation with what they have heard.
If a head confronts an administrator with “I hear that the faculty are struggling with your direct style, and you need to find another approach,” the administrator only hears a few things: The faculty have spoken to the head of school about the administrator, the head is using faculty language as a starting point, and it is up to the administrator to fix things. This can create a defensive response, and the administrator is likely to feel that the head is on the faculty’s “side.” Instead, if the head asks open-ended questions—like “What are you learning from teacher feedback?”—the administrator can explore and problem-solve rather than defend.
Listen. When the head listens carefully to the answers to these questions, the administrator will be encouraged to talk freely and openly. When the administrator has space to identify aspects of the situation and share how it affects them, the head can focus on what the administrator is really dealing with. It also puts aside the expectation that the head will have an answer to the situation. This feedback is about the administrator and the faculty; the head doesn’t need to fix anything—the head’s role is to hear what is at the heart of the feedback.
Reflect. By listening intentionally to the administrator, the head can use words to capture what they have heard and identify the administrator’s posture, tone, or affect: “What I am hearing you say is…” or “I am seeing that you feel a lot of concern about the situation.” By using the words spoken by the administrator and naming their behavior, the head is not judging or editorializing. The conversation is moving forward with more information-sharing, and the administrator has an opportunity to say out loud what they are thinking. The head has not weighed in with an opinion or a solution. By pacing a conversation with reflection and observation, the head lets the administrator take in the information without feeling judged and then, hopefully, be encouraged to unpack what is happening, rather than defend their actions.
Good Talk
Tapping into these skills may not be easy in the moments when a head is confronted with an angry or upset parent, trustee, or faculty member, but they do help lower the heat of the emotions and enable people to see the elements of a situation more clearly. This can keep them from being overwhelmed by their emotions—and those of others.
With leadership coaching, Sarah explored these skills to move conversations toward building capacity and trust. She’s now entering conversations with curiosity and is regaining her footing as a leader. She said to the teacher who parked in the 15-minute spot, “Your morning routine sounds challenging. Are there any accommodations we can make for you?” She has acknowledged the challenge, asked a question, and offered to work on a solution. The teacher might think again about mentioning his expensive shoes, but the ailing in-law and troublesome knees are compelling factors, and Sarah has a greater understanding of what this teacher brings to work each day.
Healthy dialogue can flourish when we slow down and work together.
Coaches’ Corner
Have an issue you’re grappling with? Ready to reflect on your personal and professional journey?
Don’t miss the NAIS Coaches’ Corner in The Quad at Thrive 2026, the NAIS annual conference in Seattle, February 25–27. Take advantage of a free 45-minute session with educator-focused coaches and others trained to listen, ask powerful questions, and create a space for reflection. Sign up in the conference app; walk-ins are welcome on a first-come, first-served basis.