Learning to have difficult conversations as a school leader

When I was looking for my first senior administrative position, having difficult conversations was my biggest fear. I clearly remember when I recognized this as a growth area. When I was an associate principal, we had a student in our high school whose parents were going through a messy divorce. Arguments about custody and poor communication between the parents resulted in the boy waiting after school for hours to be picked up one day. When I reported the situation to the head of school, he told me to call the father and let him know we would not allow his son back into school without a monthlong schedule of who would be picking his son up every day.

I was so shocked at being asked to do this, given my minimal administrative responsibilities, that I just left his office without asking to be relieved of this duty. After finally mustering the courage to call, I stuttered out the news to the child’s father. I could hear the anger in his voice as he thundered, “Do you mean to tell me that you aren’t going to let my son back into school until we get you a schedule of who is picking him up for the next month?!” A number of answers flew through my head, including, “It’s not me, it’s the head of school!” I also considered just hanging up and blaming a bad connection. Instead, I just said “yes” and was shocked when he said “OK” and then hung up.

My journey from someone terrified to deliver any difficult news to a successful principal who was comfortable having hard conversations was punctuated by several key shifts in my thinking.