Mastering Tough Conversations for Heads of School

By Laura Fuller,
TEG Search Consultant and Executive Coach

This is the final post in a series on “Having Tough Conversations” by The Education Group.  

Heads of school, like most, if not all, adults would like to avoid having tough conversations regardless of whether it is for personal or professional reasons.

There may be a few outlier heads of school who relish the power they have over most of the other school constituents and enjoy wielding it in the decisions they make and the conversations they have with students, faculty, and parents. Frankly, these are the heads who typically do not last in their positions and, unfortunately, rarely seem to understand why. Thankfully, this is also the small minority of those who aspire to school leadership.

How new heads of school can manage expectations about tough conversations.

Most heads of school enter their new position telling themselves they will not make any changes or big decisions for the first year, that it will be a “listening year.” This usually does not work out as schools are dynamic institutions with various moving parts.

There are bound to be multiple times throughout the first year and beyond when a head of school must have a difficult conversation regardless of what led up to it. The first instinct is often to avoid the conversation and hope the situation will rectify itself. As all experienced heads of school know, this rarely works out. In fact, avoiding difficult conversations often creates a cumulative negative impact on the school community. The resulting issues become greater than initially determined.

Procrastinating about difficult conversations is one of the most damaging practices heads of school can do. Once decided that the conversation must  happen, regardless of the person(s) on the receiving end, a systematized approach can help dilute their intensity and provide a school head an orderly approach that takes away the danger of being caught off guard during the conversation.

Check out the TEG’s tips for having tough conversations.

The formula for tough conversations.

Several years ago, an experienced human resource professional gave me a simple formula to use during difficult conversations. I used it extensively as a head of school and was disappointed in the results when I failed to apply this construct.

LQERT is the acronym I applied to each conversation when I was a head of school:. 

Listening: We all intuitively know we need to listen but don’t often take the time to listen thoughtfully and thoroughly. Listening at the beginning of a tough conversation has so many essential benefits: 

  • You learn more about the situation that led to the need for this conversation.

  • While you thought you understood the scope of the problem, you instead discover that there are multiple layers of complexity to the situation. 

  • Listening shows respect for the other person and empathy for their side of the conversation.

Questioning: Asking questions is an important step that most people miss. It is a significant trust-building device that typically changes the entire tone of a difficult conversation. Even if you think you understand the necessary details of a situation, asking questions helps you gain clarity and implies that you're willing to work with the other person to understand their side of the issue.  

Empathy: Do not miss this step! It is so important to empathize with the other person. It doesn’t mean you have to agree, but you do need to show that you have compassion for the situation that led to this conversation. 

Response: This is the step we often go to immediately or at least too often. We’ve formed a plan in our heads for how this conversation will proceed and launch into the response part of the exchange without going through the “L” and “Q” steps. The result is an emphasis on the imbalance of power that so often happens when a head of school – seemingly the one with the power – has a difficult conversation with a student, teacher, or parent. Skipping to your response puts the other person on the defensive as they perceive your lack of interest in their explanation of the situation that led up to the need for the conversation. 

Testing: Another step so often missed when the conversation has reached a point that feels satisfying to the head of school. He/she has responded with his/her opinion and feels that the solution is complete. The problem is that the person listening to the head of school’s summary may not have such a clear understanding of what’s ahead. It is vitally important to test or summarize the solution and make sure the recipient thoroughly understands your response.

Some heads of school shy away from this last step as they are afraid to find out that the person is not compliant with the solution. The conversation will be virtually useless if the recipient is confused or resistant to the results. 

Parents especially, and often faculty, need to believe they “won” something in the conversation. They need to feel there was give-and-take and that they were not completely ignored or overruled. It is always important to look for a win for them regardless of its significance. Often providing the smallest detail supporting their side of the conversation can be effective. 

Avoid the ripple effect.

New and seasoned heads of school are bombarded almost daily with problems to solve. Additionally, they feel pressure from their boards, faculty, and parents to be consistently improving the school. It is often easier, more interesting, and less conflicting to work on school improvement and look the other way or hope for self-resolution when the inevitable problems arise. 

Long-tenured heads of school know that avoiding tough conversations may seem desirable at the moment, but inevitably, the ripple effect of this avoidance is a much larger, more complicated situation. Typically, this means far more damaging repercussions than if the problem had been dealt with swiftly and efficiently in the early stages.   

Need more help with tough conversations? Check out TEG’s other posts in this series:

An Independent School Leaders’ Guide to Tough Conversations by Katherine Moncure Stewart, TEG President 

Resources for School Leaders for Having Tough Conversations by David Dougherty,

TEG Search Consultant/Executive Coach

How can TEG’s Executive Coaching program help you better navigate leadership challenges? Contact Katherine Moncure Stuart, TEG President, at katherine@educationgroup.com.

At The Education Group, we are experts in guiding schools through searches for heads of school and other top positions. Our coaches and consultants are experienced, former school leaders who tailor searches, coaching, and consulting to your school’s needs and goals.