By Jane Taubenfeld Cohen

“Help me write my letter of resignation.”

“I don’t think I can do this anymore.”

“Can you talk? I am dying”

Last week, I received these three text messages from three different, very talented leaders. All within the span of 20 minutes.

And so I ask:

What is going on with our field?  

Is the job of Head of School doable?  

Why do leaders, many of whom are in their first 5 years on the job, feel so lost, feel so lonely, feel so inadequate?  

Are the crises in leadership not only about the lack of candidates and the fact that people are leaving, but also about the pain of those who are staying?

Let me be clear. Those Heads who work in schools with endowments or major donors, who are not worried about the finances and/or the admissions’ numbers, are not feeling the same pain. But for all the others (which is the majority by a long shot), those two worries are prevalent. These worries leave the HOS vulnerable to all kinds of scrutiny and feelings of failure and, when that comes with a lack of support, the scrutiny and response to the scrutiny becomes the main job of the HOS. When this happens, that HOS loses his/her passion (not that they can’t find it again but, for now, it is lost), loses his/her ability to be innovative, loses the desire to do the job. Not always. But often.

And this is on us. Whether or not you are a lay leader or a parent in a Jewish day school, if you are an advocate for Jewish day school education, it is on us. We have to look at it and we have to join together and we have to find ways to remove the scrutiny. Not all of it; obviously we want heads to be evaluated and get feedback, but the micromanaging scrutiny has to go away. We have to give the support and to insist that we are not seeking perfection. Most importantly, we have to be a friend – it is on us to take away the loneliness.

I have a unique lens. I coach a lot of heads of school and other school leaders. I do this work both on YOULead and as a senior mentor on DSLTI. My life and work are filled with school leaders. I was a Head of School for 22 years. I want to take this on. I want to figure this out. Not just through my coaching, but as a Jewish community. I think we have to. Otherwise, our best people will not become leaders or will not stay in leadership. We will create an even bigger problem for our schools. And the victims of that will be our children and our future. Big enough stakes?

Let’s have the conversation.

A new organization is starting this summer that will work with schools of all shapes, sizes, and beliefs. I, as part of this new organization, want to think about convening to talk about this. I don’t only want to talk to the professionals. We need the lay people in the room. Who is interested? Please comment below.

Jane Taubenfeld Cohen is the Executive Director at the YU School Partnership. Prior to joining YUSP, she was the Head of School at the South Area Solomon Schechter Day School for twenty-two years, where she was one of the founders. In addition, Jane has been a mentor for 8 years at the Day School Leadership Training Institute (DSLTI) and she now works with alumni and as a mentor to new Heads of School. Jane can be reached via email at jcohen11@yu.edu.

Cross-posted on The YU School Partnership Blog