Journal Entry XXVI:

For your final journal entry, please submit a reflection where you share highlights, favorite presentations, questions raised, and lessons learned from your time in the program.

One of the largest challenges facing leaders in independent schools can be boiled down into one central question: “How can we do good and do well?” Unlike their counterparts in the public sector, independent schools serve a dual purpose: first, as businesses and second, as educational institutions. This duality also becomes a dichotomy, since at times, these demands seem to oppose each other. The question of whether the goal of schooling is public education or educating the public—which at first glance seem similar but are vastly different in execution—is nowhere bigger than in independent schools, which need to prioritize operating in the black and sticking around beyond the current fiscal year. Indeed, this is the reality that administrators face each day and that many teachers working in independent schools are privileged not to consider.

The second semester introduced more nuance to an arguably cynical version of myself, one who entered the School Leadership Program after a tumultuous first year at Barrie and after some tough years at St. Albans School. Indeed, I carry with me some trepidation, if not outright anxiety, as this school year ends: Within days of each other, Jon will begin his next chapter, Ben will take the helm, and Ah-Young will return from maternity leave. On top of that, Barrie’s financial stability is shaky at best, with our school operating in a deficit once again. I remain cautiously optimistic about Ben’s arrival at Barrie and his reception here. In many ways, Ben will build the plane of headship as he flies it, which aligns with what all of us in our respective administrative roles face in our everyday work. However, I carry with me the wisdom of Jen Danish, Head of School at Grace Episcopal Day School, who said that my job now is both to manage and to mentor up. The task is seemingly daunting, but I feel more prepared now to take on that responsibility than I was in August.

I attribute part of this confidence to a combination of what I have learned on the job and in classes. One reading I return to frequently is Ron Heifetz et al. (2009), who distinguish “technical” from “adaptive” leadership, noting that certain opportunities call for technical leadership, while significantly more challenges necessitate adaptive leadership, especially on the systems level (p. 7). In a similar way, they also highlight the metaphor of viewing matters in an organization on both the “dance floor” and the “balcony,” as understanding an organization requires looking at its needs from every angle (p. 30). Steve Piltch has reminded me repeatedly, though, that before I look at the proverbial dance floor and balcony of the organization, I also need to check to see if a foundation even exists in the first place. “Barrie needs one, because it doesn’t right now,” he has said multiple times.

This foundation is rooted in the identity and mission of the school, which should go hand-in-hand with the academic program. During our Fall Expeditions college tours trip with our juniors and a handful of seniors, we saw Princeton. At the end of our visit, our tour guide, sitting down in front of the speaking union, concluded her tour with the answer to the question, “Why Princeton?” to which she responded with something like this: “You will hear on many tours that a central reason that many people chose their college or university is ‘the people’: the students are great, the professors are brilliant, and the community is strong. However, you will get that anywhere you go. What you want to pay attention to is what the school can provide that no other school can give.” She then rattled off all of Princeton’s successes in that field, from athletics, to research, to need-blind admission.

Barrie cannot answer this question, for it struggles to have an identity of its own. In fact, I know this because everyone on the administrative team has a different answer to the question of what sets Barrie apart. Patrick Sillup provided me with a way to phrase this question during Strand in February on principal/administrator evaluation. In it, he mentioned a simple exercise he engages his senior leadership team in, which is to fill in the blanks: “We are a school where x learn(s) to be y” (2024, February 3). He noted that this is a “good exercise for helping articulate your school’s vision” and that “[if] you do not connect [what we do] to higher elevation, [then] you don’t land” (2024). Patrick also mentioned that “we are the products of our expectations,” a line that reinforces something that Colgate University President Brian Casey said to the Alumni Council literally the day before in New York City: “Stay comfortable with the notion that you are pushing an institution to do big things” (2024, February 2). We are not pushing, and this is partly why we are where we are as an institution. 

I want organizations to push themselves and the people within them to push one another. The question is how I make that ask. I have learned in my 11-year career so far that I ask critical questions in ways that come off as brash. I ask good questions, but I don’t ask them well. The soft launch of DG Strategies in August of 2023, days after the beginning of my Penn program, served as an opportunity for me to push myself to reflect on how I ask these questions. When this academic year concludes, I will launch my consulting company in earnest, for I feel that I will have struck the appropriate balance between “talk[ing] less [and] smil[ing] more,” as Aaron Burr advises protagonist Hamilton to do in the hit eponymous musical. I remain grateful to Penn for giving me the chance to harness my voice and to soften it when needed. 

References

Casey, B. (2024). “Campaign Updates.” PwC, Feb. 2, 2024.

Heifetz, R. A., Linsky, M., & Grashow, A. (2009). “The Theory Behind the Practice.” In The Practice of Adaptive Leadership: Tools and Tactics for Changing Your Organization and the World (pp. 1–28). Harvard Business Review Press.

Sillup, P. (2024). “Principal Evaluation.” University of Pennsylvania, Feb. 3, 2024.