How to Navigate Difficult Conversations as a School Leader

When I first became a head of school more than 10 years ago, I’d always offer constituents a glass of water during our meetings and would keep the pitcher within reach on the table. That all changed after one difficult meeting with a parent.

During this conversation, the parent expressed her frustrations with the school and grew quite angry and animated. She leaned forward over the table and waved her arms in anger and knocked the glass of water and pitcher all over me. The meeting froze, and the parent immediately got up to get some paper towels.

My assistant walked in, saw me drenched in water, and asked me what happened. The parent came back, cleaned up the mess, and sheepishly left. From then on, my assistant would ask me, “Is this a water or no-water meeting?” If I anticipated a tense conversation, we’d set the pitcher away from the table.
Difficult conversations are a daily occurrence for heads of school, but great mentors and years of experience have boosted my confidence in handling these situations. These are some of the lessons I’ve learned along the way about managing a no-water conversation.
Prepare physically. As a head of school, training the body and mind for challenges is key. I work out every morning so that my mind is clear, and my body feels ready for the curveballs that might get thrown at me during difficult conversations. I pay close attention to how my body feels, noting where I feel tension and tightness, and use breathing exercises to relax.  
Map your objective. Several years ago, I studied Dialectical Behavioral Therapy––a therapy approach that teaches mindfulness, acceptance and distress tolerance, emotional regulation, and interpersonal effectiveness––and learned an important construct that helps me prepare for a difficult conversation. Before each conversation, I map the sides of a triangle with my objective for the meeting, my relationship with the other person, and my willingness to have my self-respect challenged.

For me, the most important side is the objective. If I go into the conversation willing to bend on the objective because the relationship is critical to preserve and strengthen, I think through a few ways I might do that. And if I’m firm on not bending the objective (like changing a child’s grade), I anticipate how my self-respect might be challenged (unkind comments or characterizations about me or the school). I also must accept that the relationship could suffer because sometimes I have to say no.

Establish a “trust” bank account. Building the trust that needs to exist with the person you are meeting with is a key component of working through difficult conversations. One of my mentors often talked about the importance of building a “trust” bank account, knowing that there are going to be times when you need to withdraw from the account.

I work to foster connection and trust by engaging in positive interactions and recognizing a person’s contributions and value to the community. I always try to understand their lived experience and show empathy and compassion.

In some ways, a successful difficult conversation is one in which there is enough trust that there can be healthy disagreement without a deep erosion of the relationship. In fact, a really successful difficult conversation can lead to a deepening of trust. In one recent conversation, the other person and I shared personal stories with each other. In response, we were able to better understand each other’s perspectives as we moved through the conversation. It takes vulnerability to get to this level of trust.  

Notice body language. When having difficult conversations, rearrange seating in a way that gives a full view of a person’s body language, which can reveal how they are feeling. For example, people with their arms and legs crossed show tension and that they might be expecting an argument.

Pay attention to the point in the meeting when the arms come uncrossed and try to note what made that happen. I’ve noticed that it often happens when I show vulnerability or give validation. At that point, the conversation can begin going deeper to the root issue or concern.

Be ready to pivot. Before a meeting, I often ask team members to pepper me with questions that could come up in a difficult conversation, and I try to answer them. This helps me anticipate many of the different directions the conversation could go.

This also reminds me of how my nephew, who’s an avid skier, taught me the importance of keeping my knees bent when navigating bumps in a ski run so I don’t get thrown. I use the “knees bent” concept to feel ready for unexpected obstacles. Be prepared to pivot and adjust in the moment to keep the conversation on the right track.

I’ve had the experience of thinking the conversation is about one topic only to realize the conversation is about multiple topics that can go in several different directions before getting to the root issue. Being in the knees-bent stance allows me to be flexible with the needs of the other person in order to reach a resolution.

Take notes. Another mentor shared that they always took notes by hand as a way to show respect. Ever since then, I use a composition book to jot down key points that came up in the meeting. Many people have noticed that I take notes and say they appreciate how I took the time to really listen. Note-taking also helps me slow the conversation in my mind so I can respond thoughtfully.
Apply the 24-hour rule. No matter how a conversation went, another exchange is likely after the other person processes our conversation. Early in my headship, I was surprised when this happened. Now, I’ve come to expect it and recognize it as an opportunity to strengthen a relationship through more dialogue. A seasoned head once shared with me that, a few days after a meeting, she follows up by phone or sends a handwritten note to ensure mutual understanding.

I have been an educator for 31 years. Difficult conversations are part of the job, but with the right preparation, mindset, and tools, they can become more manageable and help us build and strengthen our communities. I used to have physical dread when faced with a no-water conversation, but with these strategies, I feel a greater sense of agency, empathy, and willingness to lean into difficult conversations.
Matt Levinson

Matt Levinson is head of school at San Francisco University High School in San Francisco, California.