Leadership: How to Handle Difficult Conversations

Kate Gallagher
Kate Gallagher
High school principal; M.A. in Urban Education, ESL Program Specialist
Older woman having a discussion with a younger man.

What is Considered a Difficult Conversation?

This is my fourth year as principal and seventh year as a school administrator. Having hard conversations is finally starting to feel a little less prickly. In “admin school,” as I affectionately call the series of post-graduate classes required to become a certified K-12 principal, you learn to observe and evaluate staff, but not much time is spent developing the intrapersonal skills needed to navigate difficult conversations. In fact, before some time spent in the administrative role, I couldn’t imagine some of the difficult or downright uncomfortable conversations I would find myself in. Here are some conversations and messages I have had to navigate.

  • Unsatisfactory observation results
  • Inappropriate/unprofessional staff dress
  • Students reporting that staff member of opposite sex stares at them inappropriately
  • Exhausted sick leave for chronic illness or terminal illness of family members
  • Building transfers
  • Teaching subject changes/room changes/grade-level changes
  • Facilitating staff-to-staff mediations (especially when there is romance involved)
  • Furlough/position-elimination
  • Grievance/arbitration discussions with union leadership

This list is not inclusive and these topics are not exclusive of each other, but there are several things to consider that could create some comfortability when difficult discussions must be had. These tips can also be applied to scenarios of difficult conversations with students and parents or guardians.

Things to Consider when Handling Difficult Decisions

Physical Environment

Your first considerations should be location or physical environment. Choose a place that is private and not in a public place where others are able to overhear and possibly have access to personal information. When choosing location, also consider the appropriateness of the location. Serious conversations should not happen in parking lots, hallways, or dark auditoriums. Private offices or empty classrooms are good options. Keep tissues, possibly fidget toys, and some type of soothing scent in the space, as well.

Emotional Comfortability

It is also important to consider the implications that the physical environment could have on emotional comfortability. Adults who are survivors of trauma may be emotionally impacted if they feel trapped physically. In order to establish a level of emotional safety, create an environment wherein the door is within sight and reachable.

Consider the message that your body language is sending, as well. Keep your hands on the table, arms open and not folded against your body. If possible, maintain eye contact and limit facial expressions as reactions. These actions preserve previously built trust and respect for one another.

Power Imbalance

Frequently, we have distorted images of self, which prevent us from seeing ourselves the way others see us. This is why having a strong sense of self-awareness and habit of self-reflection is important. For example, I see myself as who I am as a whole and not defined by my career role of principal. When I walk through the hallways of our school building, I carry myself and think of myself as a servant of all stakeholders within and outside of the school community. The “Kate” that others see in the hallway is their boss or principal, one dimension of myself.

This perspective creates imbalance of perceived or real power between subordinate and supervisor. It is important to put ourselves as leaders into the shoes of those we’re having difficult conversations with to create a sense of rapport and empathy and not one of top-down imbalance and separation.


In a school setting, it is important to carefully consider who is present during difficult conversations with staff. If you are a leader in a school building that has a teachers’ union, make sure to always notify your staff that they are welcome to bring union representation to all meetings that could result in disciplinary action or have previously.

This may seem like it can deepen any pre-existing divide of confidence between both parties, but I have found that it actually creates a bridge of transparency. Even if the meeting will not lead to disciplinary action, it is still considerate to offer the other person the opportunity to bring someone with them who may help them feel more comfortable.

It is also a good idea to not meet with staff alone in some circumstances. If you think that there may be a need for a second set of eyes and ears or someone to take notes, ask a colleague to join, but be sure to communicate the reasoning to the other party.


There is no doubt that not having difficult conversations is easier in the present than having them. It may seem that the benefits of avoiding these topics outweigh the discomfort and fear that you may have at the thought of discussing them with others. The most important thing to keep in mind is that there will always be consequences to whichever decision is made, to have the conversation, or to avoid it.

Inevitably, there will be victims of the negative consequences. For example, avoiding a hard conversation about an unsatisfactory observation rating will result in the teacher continuing to perform subpar. The victims of this will be students, those who are our top priority in education. By avoiding that uncomfortable conversation, you may be subjecting hundreds of students to ineffective teaching strategies at best or an unsafe environment at worst.

Without a doubt, our role as leaders is to always put students first, even if it is uncomfortable or difficult for us as adults. This is one example, but there are many more scenarios where difficult conversations must be had to protect others or to communicate decisions that are in the best interest of others. We as leaders are charged with choosing the ethical route and sacrificing our own comfortability in the name of what is right for our schools, students, staff, and families.

It is this reality that has pushed me to have difficult conversations. I’m happy to say that with practice I’ve become more confident in my ability to show empathy, create partnerships in a safe space, and communicate about uncomfortable topics more comfortably.

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