Rabbi Adam Englander
“There is a pattern that exists in the organizations that achieve the greatest success, the ones that outmaneuver and out-innovate their competitors, the ones that command the greatest respect from inside and outside their organizations, the ones with the highest loyalty and lowest churn and the ability to weather nearly every storm or challenge. These exceptional organizations all have cultures in which the leaders provide cover from above and the people on the ground look out for each other. This is the reason they are willing to push hard and take the kinds of risks they do. And the way any organization can achieve this is with empathy.” 
These words close out the first chapter of Simon Sinek’s book Leaders Eat Last. No leader can be great without having a deep sense of empathy for the people he or she is leading. No matter the type of organization, and certainly no matter the type of school, leaders can only be truly successful if they prioritize the well-being of those around them. 
Why is empathic leadership so fundamental to a strong organization? Leaders exist so that all the others around them grow and improve. This type of growth and improvement occurs most significantly when people feel a deep sense of being cared for and appreciated. And that care and appreciation must be because they are people, not simply as a function of the job they do for the organization. This reality is hard-wired into who we are as human beings. The more people feel this parent-like concern from their leaders, the better they perform. We accept this as a given when it comes to how our teachers interact with their students. It’s not much different for adults.
The greatest Jewish leader of all time, Moses, was chosen for his position by God as a result of his proclivity for empathizing with his brethren. The Midrash in Bamidbar Rabbah (1:27) goes into detail about how God called out to Moses from the burning bush only after He saw the extent to which Moses felt the pain of others and tried to ease their burden. 
Empathy can be shown in an infinite number of ways. Providing support for a teacher going through a personal crisis. Going the extra mile to attend that simchah, shivah call or hospital visit. Listening (really listening) to a student even though you are swamped with other pressing matters. Trying to help a teacher improve his teaching schedule even though you think his reason for wanting it is no big deal. Choosing your words carefully when delivering criticism so that you preserve the recipient’s dignity and self-esteem. Recognizing why that parent is getting so defensive when you bring up those concerns about her child. In essence, treating others as the good, well-meaning people that they are. 
A couple of examples from my own work come to mind. In my first year as an administrator 12 years ago, I recall a meeting I set up with a teacher, also in her first year, to convey criticism about certain aspects of her teaching and classroom environment. I don’t remember what the issues were or what I said in that meeting. I just remember being super nervous that I would crush her spirits and leave her feeling badly. A couple of days later, she initiated a meeting with me. With tears in her eyes, she thanked me for how I handled that meeting. She explained that while it wasn’t easy to hear about the things she needed to do better, it was so obvious to her how much I cared about her feelings and that meant so much to her. This teacher is still at our school and is considered a superstar. A more recent example of how our school prioritizes empathy in the workplace is the creation of a fund designated to help teachers and staff get through tough times. This fund, initiated by a parent, gives mostly small-scale, interest-free loans with very flexible terms of repayment. It has been used many times, and we often hear how much it means to our people, our family.
Since empathy is defined as the ability to understand and share the feelings of another, it’s not really something that can be faked. One has to be a good person who actually cares—which is, by and large, exactly the type of person going into school leadership in the first place. When a head of school’s or principal’s empathy seems in short supply, perhaps he or she is overwhelmed by the volume of work that the position requires. School leadership can be demanding and stressful, and it’s common to get overly focused on that to-do list and forget some of the basic needs of the people we are leading.
The first step for a leader to improve the quality and quantity of the empathy he or she displays is to recognize just how important it is for the creation and maintenance of a healthy school culture, one person at a time. The next step is to carve out time on the calendar every week to make this happen. Empathy need not be spontaneous to be sincere; a fixed routine will force a person to think about the actions that need to be taken and the people who need some extra care. If those connections can’t be made during that time slot, one should use the time to determine when and how they can happen. In other words, a leader should spend this sacred time asking that teacher about her child who was not well, writing that handwritten thank-you note for the one who went above and beyond, and finding something specific to praise about that teacher or student who has been feeling down.
However, like most things in life, too much of anything is bad. When used improperly, empathy can be a damaging force that can lead to the opposite of what good leaders are supposed to accomplish. In Radical Candor, Kim Scott, who held leadership positions at companies like Google and Facebook, explains how leaders often make the mistake of engaging in what she calls “ruinous empathy.” In their desire to be nice, cultivate relationships, give praise and steer clear of conflict and hurt feelings, too many leaders avoid the candid criticism that their direct reports need. While their intentions may be good, this can lead to people not knowing where they stand, thereby stunting the growth and improvement that should be taking place. Therefore, as important as empathy is, it can’t go so far as inhibiting constructive feedback. A healthy, balanced disposition of empathy means not shying away from the uncomfortable conversations that, on the surface, don’t feel so empathy-filled.
Empathy is not only one of the important qualities that great leaders display, it is foundational. And if this is true for the modern organizations of today, it is all the more true for our Jewish schools rooted in Jewish values.
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HaYidion Leadership Dispositions Winter 2018
Leadership Dispositions
Winter 2018