Transitions are Hard - And We Can Manage Them

We're all going through them and I have some specific thoughts for new heads and heads starting a final year at their current school.

Photo by Patrick Hendry on Unsplash

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I have several in process TOOS drafts as well as many obligations at the moment and what I thought I would be publishing this week I just don’t have the bandwidth to revise well. So given that it’s the first week of school, I offer up this lightly edited post from last year on transitions.

A wise woman said to me many years ago, life never remains static. I think about that all the time and it has more resonance the older I get.

During the first session of the pilot Boss Skills Lab, it occurred to me that a number of the participants (maybe a majority?) are experiencing a head transition at their schools. And of course, we’re all experiencing the unpredictability and uncertainty in the world. I keep thinking one of the most challenging parts of eldercare is the total ambiguity of what’s next. It’s all taxing. We make one transition only to discover another one is on the horizon.

Then there’s the best thing about social media - all the “back to school” photos! Unbelievably, many of my friends’ kids have now aged out of this wonderful ritual but I still enjoy what I get. It feels like this wonderful invitation to just be openly and unironically sentimental about transitions; it feels like all the hope of both youth and a new school year distilled in an image. The very excellent script for the welcome to the Westover graduation ceremony I inherited and had no need to edit talked to the parents about their sense of wonder that their little child had become this poised, accomplished young person seated on the risers in front of them. Never a dry eye in the house, including mine!

That’s the exciting aspect of transition.

Many years ago after a grouchy January professional development day at the end of a winter break - one I had planned - and I was definitely feeling, “stupid faculty - no one appreciates my hard work!” - my head of school said to me something so simple but so true I think of it all the time - “Transitions are hard.” I think of it when I see a kid who doesn’t want to leave the Target toy aisle. I think of it on dark and rainy mornings lying in bed. I thought of it this morning when I fished a jacket out of the coat closet because although everyone in New England is now mandated to love “sweatah weathah” (and I really, really do!) it’s hard to put on real shoes and a jacket rather than just taking the dog out first thing in a sweatshirt and sandals.

Transitions can be exciting. They are also challenging, tiring and make you use muscles you haven’t used in a while, and sometimes, haven’t used at all. The speed with which generative AI is developing is scary and the potential change it could bring to education is so fundamental and hard to fully comprehend in its scale that I find I can only contemplate it in small chunks.

There are the big, obvious school transitions, such as when a head leaves and a new one arrives, but the very fabric of school life is changing all the time right now. We try to adapt to a social media world, a world where information streams are bespoke and institutions like schools don’t have the same level of automatic public trust they used to have. We are aware of how school cultures have fallen short in terms of inclusion and belonging - the implicit promise of our independent school communities is that every child is seen and known and there were, and are, times we break that promise. And there is technology - no to students using their phones? Yes to ChatGPT for faculty lesson prep? It’s a lot!

So in addition to “Transitions are hard” for when that Monday morning feeling is lingering or “Life never remains static” for when you’re looking forward for a certain run of bad or no luck to end - here are three thoughts for times of transitions:

ONE

Accept the ambiguity and uncertainty - lean into communication

One of my main mantras is that one of a leader’s main jobs is to reduce ambiguity where possible so everyone can better go about focusing on the work at hand. While I still maintain this is true, and can be true even during major transitions, there are many factors outside of our control. During head of school transitions, there is also the compounded “authority effect” because lines of authority become blurry. Where is the outgoing head in control, when is the new head in control, when is the board in control? In an ideal world there is a solid board transition committee who is working closely with the current head to support that person until their last day on the job. This can be an art not a science, though. It can be hard for a head to let go and board members on a transition committee have to be very skilled about how to be supportive of leadership and having enough knowledge without becoming a member of staff. It’s a little wobbly and unpredictable.

TWO

Faculty and staff feel the impacts of these wobbles and they are inevitable. People in schools generally prefer predictability and routine and the longer a head has been in place, the more you notice even minor bumps in the road. The more people can talk about transition and the fact that this is all normal, the better the chance you all have in getting through it without the bumps producing cracks that might split open later in the journey.

THREE

All change involves loss - leave space for some sadness

I recently read about an end of life conversation between a daughter and her elderly father and how they cried and it was sad, but it wasn’t a sadness full of regret; it was sadness as emotional closeness. No workplace is great about managing people’s feelings and we all, as individuals, are primarily responsible for how we decide to manage our emotions. However, when relentless positivity around the transition starts to feel flat, that is not an indication that people are unhappy about the new head coming in or whatever the major change is. You can feel pretty OK about an upcoming major change and still feel sad about the loss involved in the change.

This can be really hard to do if you’re managing change, but in one on one conversations particularly, don’t shut down someone who is expressing sadness or worry. Don’t just reassure them. Engage them. Ask them what they will miss. Let there be silence if it happens. Don’t immediately explain why what they say they’ll miss, they won’t miss at all. It’s OK, and probably most helpful, just to sit with someone and say something along the lines of, “I can see why you’ll miss that” or even “transitions are hard.”

FOUR

Remember that people in authority are people, too!

Whether it’s a new head entering a community, a head leaving a community or an administrator who is the face of a major change, it is easy for the community to forget that leaders are people with complicated layers of feelings, too. You don’t need to get out that tiny violin, but just as I felt a little demoralized when my school community was grumbling about that January professional day many years ago, just multiply that by one thousand if you’re an administrator rolling out that new cell phone policy. And by a million if you’re either the outgoing head or an incoming head.

Heads starting their final year are leaving behind at least some kind of unfinished work, since the work of schools is always a moving train, and many relationships, a majority of which will be diminished if not eventually lost altogether just because life moves on and people are busy.

Incoming heads are leaving the same from their last position. And leaders may have authority but they have to earn political capital to do anything meaningful and lasting with that authority, no easy feat as you enter a community where everyone is already tired of having been in transitions for months and just want to get on with it. Everyone needs to draw on reserves of patience and as I said above, continue to lean into communication. As a community member, if you don’t understand a decision, ask rather than projecting the worst.

Of course people criticize and analyze and gossip - but people can also be kind and empathetic. Embrace the complications. Strive to embody your human complexity. And as I said over the summer, easy to complain, hard to do. Not a bad thing to keep in mind.

Enjoy the weekend! See you Tuesday with the “September Happenings” newsletter. And premium subscribers - look for an email just for you next week with details about signing up for your 1-1 meetings that come as part of your subscription.

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