by Andrew Prince, Faculty, gcLi; Head of Upper School, Shady Side Academy in Pittsburgh, PA
The idea that “it is tempting, if the only tool you have is a hammer, to treat everything as if it were a nail” is one I hear referenced often. Most folks in independent schools have more than the proverbial hammer and use their various tools in ways that make sense. And, like other tools – skills, dispositions, approaches, interventions, pedagogical practices, etc.– there are some we use more than others.
For example, I like to lead with humility as often as possible, identifying my own shortcomings or deficits and appealing to others so they can help inform the process. While this “tool” is mostly helpful, it is not well suited for moments when folks are looking to me as their division head to be the “expert.” I don’t think of myself as an expert at many things, and there undoubtedly are moments when people are looking to me to be the font of knowledge and to the extent that I can help it, it behooves me to step into that role.
I learned this best in a moment when I asked colleagues to try a restorative conversation for the first time. I asked questions and deferred to others, and the result was that one of the adults material to the success of the conversation did not follow the protocol; we failed to restore the peace between the two students. In the years since, I have come to develop a series of questions I ask myself about “moments.” I think of this process as interrogating the moment in order to determine the tool that I will use to respond. I do not mind “failing,” and it absolutely galls me when I fail for preventable reasons like employing the wrong approach. That was the impetus for adopting this interrogation.
How Much Does the Outcome Matter?
One of the first questions I ask myself is how much the outcomes matter. There is no doubt that as schools, we must focus on outcomes of all sorts – grades, presentations, assemblies, athletic contests, arts productions, money raised, etc. We also know that the process and inputs are what we should focus on because designing a good process is key to learning. How much will a moment allow us to center the process and inputs and not worry about an output?

If students are struggling to put together a presentation for a class I am teaching, I certainly want them to learn about the subject of the presentation. And I would almost certainly help the students learn the desired content if I step in and mediate an interpersonal conflict that is inhibiting their efforts. However, I would be robbing them of a chance to mediate an interpersonal conflict which I personally think is far more important than their learning of the War of 1812, for example. That is, as I get up to the proverbial balcony and evaluate the moment, I can see that the costs of a “bad presentation” are not so much and the benefits – an understanding of the importance of group dynamics to performance – are substantial. However, if this were a presentation for the full school, the board of trustees, parents, etc., my calculus might change.
Answering this question will not spare you from a difficult decision – I have let assembly presentations flounder before and it is always a relatively high risk/high reward moment – and it will help you make an informed difficult decision.
Who Needs to Know Now?
A second question I tend to ask is who needs to know now? I add the emphasis because timely communication to those who have a deeper interest in a given “moment” is vital for a couple reasons.
First, there are few moments of consequence where having all of the relevant parties at the table is not helpful. The more people present who are informed and connected, the better chance we have of getting to the right place – this is of course a core tenet of inclusion and belonging efforts.
Second, “moments” have a way of impacting communities and all constituents on a personal emotional level. Beyond the work that each of us does to respond to stimuli in our schools in our professional capacity, we are also full humans who are impacted by our work in myriad personal ways. I’ve been brought to tears of joy and anguish and everything in between while working in schools, and I imagine that most of my colleagues have before, too. For this reason, it is important to both identify and contact those most proximate to moments to give them all of the information that you can reasonably provide while voicing your concern for the entirety of their being.
I have had what I thought of as “good responses” to moments more or less ignored because I did not communicate in a timely manner and other responses that I saw weaknesses in that people did not resent because of timely communication.
What Do People Want and Need to Know?
Many moments in schools require communication to a larger audience at some point, whether it is the full community, a grade level, or particular constituency.
Increasingly, moments make people want answers, clear statements of principle, outrage, support, and more, and they will certainly want an action plan. Unfortunately, answers and clarity frequently come with work and time which is rarely comforting to folks who are impacted by a moment. These are times when the Heifetzian maxim of “disappointing people at a rate they can manage” feels especially relevant. I find it helpful to share what I know to be true which in terms of facts, may not be much. If I don’t have the facts of the moment, I do frequently have feedback from constituents about how the moment and the lack of details has impacted them, and I do include some nod to this in my communication. If people are telling me they are mad or frustrated or some other big emotion, I’ll give voice to that in my communication. This act of “seeing people” has almost always bought me more time to do the good work with the right people to eventually share more details and more plans.
Moreover, I make sure to remind people of who we are as a school and how our mission/motto/core values might be relevant in a moment. In times of duress, people can stray from guiding principles and as school leaders, we allow this to happen at our own peril. I tend to think of guiding principles as aspirational, and by elevating these guiding lights, we can help our constituents to respond to moments in a manner informed by our commitments to one another as members of a shared school community.
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Andrew is the Head of Senior School at Shady Side Academy in Pittsburgh. Prior to his time at Shady Side, Andrew worked as the Head of the Upper School at the Collegiate School in NYC, Dean of Multicultural Education at the Taft School in Watertown Connecticut. Andrew has also taught at Montclair Kimberley Academy, Chinquapin Preparatory School, and volunteered as a part of the Jumpstart program which teaches language and literacy skills to preschoolers. Andrew earned his A.B. from Harvard University where he studied Political Theory and minored in Moral Political Philosophy and his M.A. in Private School Leadership from the Klingenstein Center at Columbia’s Teachers College. Andrew lives with his wife Courtney, sons Austin and Archie, and two (big) dogs, Toby and Ginsburg.

