I’ll give you my example of tone deafness. During my son’s time the athletic director wanted to kill the squash program – basically he said it was an elitist sport. He made it very difficult for kids to train with coaches on the Lville squash courts. This caused an uproar with the parents and athletes.
The headmaster buried his head in the sand and refused to meet with parents or listen to our concerns. One of the parents had a connection with board of trustees member. Even after that the headmaster didn’t acknowledge our concerns. Later, after my son left, I heard about instances of bullying that led tragically to a student suicide.
The headmaster and his/her leadership style says a lot about how the school functions. While I wouldn’t choose a school solely based on the headmaster experience, please note that his leadership style left a bad taste among many parents.
My son loved his time at Lawrenceville and stays in regular contact with many of his housemates. He probably would have made good friends at Andover too. There really isn’t a wrong choice here. Just be mindful of the pros/cons of both options.