Screen Shot 2014 09 28 at 1.06.55 PMArch Montgomery grew up on boarding school campuses and went to a boarding school. His father was a boarding school headmaster, and his mother was Chair of a Board of Trustees for two decades at a boarding school. Boarding school is in his blood. He began his teaching career at St. George’s School in Rhode Island where his duties included supervising a girl’s dorm, coaching football, swimming, and lacrosse, serving as Chair of the History Department, acting as Assistant Director of Athletics, teaching a wide variety of history courses, advising the debate club, and directing the Summer School. He was subsequently appointed Headmaster at Gilman School in Maryland before accepting the Head of School job at Asheville School in 2002. He enjoys the outdoors and particularly enjoys fly fishing and hiking in the mountains. Arch earned his B.A from the University of Pennsylvania and his J.D. at the University of Texas School of Law.

My friend, Andy Hirt of TABS, asked me to share my thoughts in the form of a blog, yet he gave me little direction. Total liberty to write whatever you want is more a burden than a freedom simply because you cannot blame anybody else for your callow, shallow, or simply ordinary thinking. He said that I should write for my peers, fellow heads of school, but I know these people. Any wisdom I might have has long ago been mastered by them. My conclusion is that I should not try to share anything that I think I know; instead, I will wonder publically about the things I do not know. That is a deep well of material. My hope is that readers, if there are any, might have the wisdom I seek and be willing to comment, thereby educating a headmaster who has more questions than answers.

Most of us have by now seen the movie, “American Promise.” Ellen Stein is the courageous head of school at Dalton where film makers spent at least twelve years observing two African American boys and their families navigate the unfamiliar waters of the independent school world.

Dalton is a day school, not a boarding school, but some chastening messages seem worth consideration by those of us in the boarding world, especially in the context of KIPP Academy’s puzzlement about why so many of their African-American boys do not thrive as expected after their KIPP experience.

First wondering aloud: do our black boys or black girls do better after they leave us? Is there a success gender gap among black children that is not true with our white students? If we study that, and it turns out that there is a gap, is it enough to say that this is a simple reflection of a larger cultural issue? That seems like ducking the issue. If we have not studied this, why not? What is it that makes sustained success over time for black male children (even those at our schools) so elusive? We can take refuge in some success stories, and point to those stories with pride – justifiably so. It is worth celebrating when a youngster who faces severe economic and cultural disadvantage thrives and succeeds. But how do we feel we are doing with our African-American boys overall? How do we know?  And if we are doing really well, why aren’t we sharing the formula that might help solve one of our country’s greatest cultural problems? As far as I know, none of us is sharing such information. The silence feels deafening.

Second wondering aloud (possibly related to the first wondering, but, frankly, I am not sure of the relationship.): Our girls seem to be performing at high levels and becoming college women at rates startling enough to make college admission officers struggle to admit boys as qualified as the girls. Yet Nan Keohane and Shirley Tighlman (former Presidents of Duke and Princeton respectively) were puzzled by the failure of their female students to assume leadership positions.  What the heck is going on here? Are we merely struggling with a bumpy transition from a patriarchal system which causes lingering sublimation of female talent to male domination despite superior female ability? Regardless of the answer to that question, how do we support our girls in this transition to become strong female leaders while simultaneously supporting our boys who mature late and underperform in high school compared to their sisters?

Two wonderings in one blog are enough, and I invite your wisdom and your wonderings in the hope that together we might find a path toward helping our youngsters – male, female, black, white, etc. – thrive in our care.

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