Stranger in One’s Own Community: A Head of School Allegory | Joel Backon | 11 Min Read

The Head of School in this story is a composite character based on the author’s work with several school Heads. While the circumstances may sound familiar, the characters are not real. Our fictitious Head of School, Dan, may appear in future stories as well.

It was to be a long flight home with my wife and two children on this early August day. We had spent two weeks based in Kathmandu, and had hiked and climbed to the base camp of Mount Everest, an ambitious undertaking. Almost the entire trip I was disconnected from anything to do with the private school I led in the U.S., and that resulted in my feeling rested and relaxed until I boarded the first leg of the flight home. Then the terror of what I might face when I returned to my office in three days began to consume my imagination, and the relaxation transformed into a mountain of stress. 

I stepped into my office very early on my first day back, marking the start of my fifth year as Head of School. My goal was to catch up on email prior to the arrival of my senior staff and my assistant, who would no doubt have a mountain of messages for me. The first email was fairly benign. It was from Bill, the Board Chair, following up on our Board Retreat just before my departure. When would I have an outline of our next strategic plan so we could establish the appropriate committees before everybody got busy with school opening? That was a seemingly easy one, particularly since my assistant, Eve, had left a copy of the last plan on my desk.

The next email was not as benign. It was from Lacey Jackson, chair of the Parents Committee, and the subject was “What’s this anti-racism bullshit?” My auto reply told correspondents that I would not be returning until tomorrow so I had time to reflect on my response to Lacey. 

The remainder of the emails were not critical, and Eve would handle most of them by scheduling meetings, the bane of my existence. I estimated spending 6-8 hours per day in meetings, meaning that most of my other work had to be completed in the evening or on weekends. I picked up a cup of coffee from the staff room and walked to the conference room where I would be greeting my senior people for the first time since the late June Retreat. This meeting would likely take the better part of the day, and there would be many action items to address over the next few days. I sometimes wondered whether it would be helpful to have an associate head or co-head dealing with many of these daily issues so I could focus more on the longer-term needs of the school and the people I served. More on that to come.

The first senior staff meeting of the year is always a challenge because the topics run the full spectrum of issues and most of my staff believe that if they don’t raise the issue today, it won’t get the appropriate level of attention (translation: it was hard to get one-on-one time with me). My inclination was always to go around the table and give each senior staff member an appropriate amount of time to be heard. The idea was to encourage collaborative problem-solving.

We began in listening mode as our facilities director and IT director summarized the projects that had been completed over the summer. We had one question to consider. What course of action would we take to address the issue of ransomware (a school 10 miles away had their systems locked in June and had to pay $50,000 to recover them)? I told both our directors to research the options and report back to us with a proposal. It just wasn’t a topic for the first day.    

We then had a round-robin with our academic leaders and briefly discussed the following issues, many of which would be taken up again shortly. My style was to avoid making decisions until I had sufficient input from the dean most impacted and sometimes delegated that decision. Our dean of faculty’s plate was full of some of the most challenging issues: faculty morale, our earlier decision not to offer a remote student option this fall (would that change with the Delta variant and increased parental pressure, and if so, how would that impact a faculty that already suffered from lower morale?), and a complaint from an alum about inappropriate contact by a former faculty member. I asked Eve to schedule another meeting tomorrow since these topics were sufficiently meaty and potentially catastrophic to require further discussion.

Our Academic Dean was also interested in the remote student option so we added her to the attendee list for tomorrow’s meeting. She also wanted to know if we were moving ahead with our schedule changes in a year or would we rethink those changes given our experiences with COVID? Our dean of students wanted to participate in the remote student option conversation so he was added to the meeting as well. He then reported that two of our students had been arrested three weeks ago for attempting to buy alcohol with fake IDs. When the police arrived and the two were cuffed, one student shouted a series of obscenities before announcing that he was a student at our school, and therefore the police had no jurisdiction. I asked our DoS to find any precedents for such an incident, look at the relevant handbook policies on the reach of the school, and make a decision unless it was to dismiss one or both of the students. Then I wanted to understand the entire story and the rationale for the dismissal recommendation. Finally, our advancement director reported that two significant pledged gifts were held up due to that inappropriate former faculty contact with an alum from the same class. I invited our advancement director to tomorrow’s meeting on the topic.

As I returned to my office at the end of the day (we had heard, in detail, how the opening of school would unfold in addition to the other issues), I felt like a stranger in my own school. The people around the table, all very good at what they do and very loyal to the school, were far more engaged with the school community than I was. For many of the mundane issues that were important to them, their questions were more passionate than my responses. Did it appear that I did not care? This was a time when having an associate head or co-head would be helpful because they could carry some of the load and be a sounding board for me by being a confidante and knowing the players well. I had discussed the matter with a peer at an association heads’ conference last spring, and his advice was somewhat unsettling. He told me that running a school these days was far too complicated to afford the head with the luxury of participating in the daily events and emotions of the school. If I tried to do so, I would be sacrificing the longer-term viability of the institution: protecting the endowment, ensuring a pathway to the future, keeping our clients happy, and ensuring that we had a sound fiscal plan for longevity. I considered myself lucky that my Board still respected and liked me after four years. They understood the constraints under which I was operating and encouraged me to keep doing what I was doing because, in their view, it was working. Our school was a happy place that balanced innovation with tradition and had strong college admission results for a school in our category, they said. Our board chair often told me that I make the most of what we have, and he wished we had more.

I felt like I should go home, eat dinner, and try to counteract any potential jet lag from which I might be suffering. I couldn’t leave, however, without thinking more about the strategic plan and responding to Lacey about our anti-racism program. These kinds of tasks were right up my alley, but somehow I felt inadequate addressing them because of my “stranger” status. I just lacked the details to do anything more than paint a broad picture of the issues with little connection to the minutia that defined who we were as a school today. At that moment, my Dad called, interrupting my melancholy musings. I had forgotten to check in with him when we arrived home the previous afternoon, so he and Mom were worried. I told him we would come to visit in a few weeks and share pictures of the trip, but right now, there were some things I needed to finish and I was tired after a long first day back. He sensed my mood and asked what was going on. I told my Dad that some days this role seemed overwhelming, and there were just too many details to digest and do the job well. Having attended the school (my daughter was the third generation), he gave me some advice. He said a leader’s job was to lead, not manage. He understood that the school was somewhat small so there might be a few managerial responsibilities, but my primary task was to orient the school to a vision of who we are and who we will become by maximizing our strengths and minimizing our weaknesses. God bless him. My Dad always knew what to say.

Now I was feeling the synergy between our upcoming strategic plan and Lacey’s concern about anti-racism in our curriculum. I had learned last spring at a workshop that DEI and innovation are covalent. They share bonds, even though they appear as very different entities. I understood that we would make little progress in one of these areas without progressing in the other. Lacey had made her feelings known at the spring parents committee meeting. She spoke with me after the contentious meeting, and let me know, in no uncertain terms, that there was no need to overhaul the curriculum in order to accommodate theories about racism in our country. She would take care of that with her own children as would other parents and didn’t trust young faculty members to present a balanced account of the history of racism. She also hoped that our move to fewer and longer classes per term was not a smokescreen for integrating those narratives. As I reflected on her remarks, I thought about the connection to our strategic plan. Could we be an independent school of 2026 vintage if we ignored the narrative that explained the importance of equity and inclusion?

I knew a few things about the independent school world in which I had lived for most of my life. While I was polite with my HoS colleagues, I disagreed with many of them on key topics that impacted our schools. I understood privilege both from a personal perspective and from the perspective of providing outstanding education to children of privilege. I also understood diversity as a means of providing a broader and deeper education to our students, and that diversity was the front end of an educational mission that also included equity and inclusion. Without the latter two qualities, our school would simply be a privileged institution with token diversity, creating the appearance of enlightened education. “We study history to understand the present.” Given that oft-quoted principle from my history department, I think we had the foundational assumptions for an effective DEI program, and that would be central to our strategic plan. Out of the goals for improved equity and inclusion, we would identify specific initiatives to meet those goals, and lo and behold, those initiatives would benefit all of our students (equity) and bring the community closer together (inclusion).

Given that skeletal plan, what would become of our mission statement? The current mission could be effectively employed at many schools and did nothing to distinguish us. Perhaps we weren’t unique until now. If so, it was time for a mission that painted a picture of a school that was striving to educate kids to be better human beings as well as having the skills and competencies to succeed in life. To live up to that mission we would have to change a number of practices: schedule, grading, pedagogies, feedback systems, how we update curriculum, values, and behaviors that are measured (and thereby demand feedback), elimination of course levels and tracks, and revising criteria for our most selective programs. That is a tall order, but we can do it in five years if we have passionate support for the basic principles: privilege is not something to be protected; it is something to share. As a selective school, we can’t pretend that we are performing a service to the greater society. We are not at the current time. We are reinforcing inequity and exclusion by our very nature. But we can be more equitable and more inclusive; in fact, we have to be or we will be remembered as one of those institutions that perpetuated the myth of meritocracy. 

What I am imagining is a profound shift in the landscape of independent schools, and I’m certain my father would say that the changes resulting from this shift will not be delegated to new senior positions or existing members of my senior staff. This is my vision that needs to become a shared vision and I have to lead my school forward, delegating only after the community buys into our program each step of the way. If I do that, if I show true leadership, I will not be a stranger in my own community. I don’t have to dive into the details to be welcomed; I simply need to inspire others to dive in, knowing that I have their backs. So, Lacey, you will be unhappy with my email response, and if you feel it is necessary, I will support your efforts to find another school for your son, Sam.

Joel Backon

Joel Backon is the Editor of Intrepid Ed News, responsible for all educator content on the website. He joined the OESIS Network as Vice-President from Choate Rosemary Hall (CT) where for 27 years he held key roles in Information Technology, Academic Technology, classroom teacher, curriculum designer, and roles in academic and student advising. Joel leads the online and professional development initiatives through the Intrepid Ed News website and a variety of other platforms. He has been an OESIS Network Leader since 2015.

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