Yes, the spring of my Millbrook son’s sophomore year, Drew Casertano told me he could tell my son really wanted to make the Varsity soccer team because Drew saw him every afternoon, practicing with the school’s best striker. I am certain this would not have been noticed at a bigger school. And Drew was right, soccer was very important to my son. I think it is impressive the head of school knew this about my son. And reflects Drew’s vision that every student be known, and appreciated for who they are.
I agree with @doschicos that the Head’s role is much more than speeches and small talk. Malcolm McKenzie, at Hotchkiss, had a very strong international vision, so that he actively recruited kids from places like Afghanistan, the Palestinian Territories etc as well as creating a senior administrative position for International studies, among other things. He left, and subsequent heads, while of course having a global perspective, have not emphasized the international aspect as much. So that senior administrative position has lapsed, there are no students from more unusual countries etc. So he influenced the direction of the school, but since he was only there for something like ? six years or so, that vision is not something that permeates the school, and the focus has shifted away.