By Rabbi Yossi Kastan

[This is the third in a weekly series “When and how does effective leadership make a true difference?” written by alumni, staff, and faculty of the William Davidson Graduate School of Jewish Education of The Jewish Theological Seminary.]

We often hear about the need to develop Jewish leaders. I have, however, never heard of a desire to cultivate future Jewish managers or even seen an advertisement for such a position. Of course, we all know the inherent differences between management and leadership. We’ve read the literature and seen the TED Talks. In fact, they have become a cliché to describe different types of executives and their exclusive functions. Still, when it comes to our positions as heads of schools and CEOs of communal organizations, why do so many of us often feel that we are “managing” rather than “leading?”

From HR matters to financial issues, we face hundreds of decisions per week, day, and hour. To keep our organizations moving, we often make snap judgments that we believe are the best in the moment. As good managers,we even take the time to think through the organizational, political, and financial implications before each resolution.

But, even when we become incredibly efficient decision makers, how many of us consider the implication to our Jewish heart and soul before making a choice? If we were being completely honest, do we go home at night feeling like the organization is running us? (From a superficial standpoint, if your preplanned schedule and list of priorities are consistently hijacked by the crisis-du-jour, and if lunch and exercise become a luxury, then your organization might be running you).

I would suggest that the issues that weigh most heavily on us are those that really challenge the integrity of the institution: a major donor believes a program should be designed contrary to best practices; a parent wants an exception made; a staff member operates in ways that compromise the mission of the organization. They weigh on us because as Jewish leaders, we consider the missions of our institutions our personal missions. When we feel compelled to make decisions that compromise our beliefs, we don’t simply see these as institutional challenges, but as personal indictments. We try to “manage” political or financial pressures, and appease those who demand. Appeasing, however, becomes a slippery slope where we lose our own direction. This process allows others’ needs, wants, and behaviors to hijack our own sense of self and remind us that our organizations are running us.

Core Leadership Exercise

Many have said that the best way to navigate the Jewish field is to have a shrewd mind and thick skin in the office and to be your true self when you get home. But this approach asks us to be managers by day and leaders by night. Our organizations and communities need us to lead. Now. Always. Leadership comes to life when we come alive throughout the process.

Fitness trainers remind us that to get physically stronger, we must strengthen our core. A strong, stable core helps us produce and transfer force through the rest of our bodies and all its dynamic movements. Let’s use core exercise as a metaphor for our work. Every challenge, every demand, every issue can help us get stronger. But if we define strength as a shrewd mind and thick skin, then we are missing a tremendous opportunity to strengthen our “core,” to reflect on whom we are inside, to consider what we stand for, and to emerge as a more stable values-based leader.

Core Leadership Exercise, designed to move us from manager roles, has three distinct phases: Reflecting, Validating, Courage-ing. (I know that “courage-ing” is not a word. For our purposes, let’s pretend.)

Reflecting: This first phase helps us understand the real issue hiding below the surface. Consider:

  1. What triggers bring me to this space?
  2. What targets are these triggers hitting inside of me?

Validating: Calibrate your own self within the stress at hand by asking:

  1. When these triggers come up, I find myself operating from a place of _____.
  2. Ideally, I want to operate from a place of _____.

The response to number one reveals the place from which you feel externally compelled to operate. In considering number two, you can understand what you want to bring to your role. If you feel forced to operate from a very different place, you are experiencing a spiritual form of identity theft.

Courage-ing is the act of becoming fully transparent, openly and clearly advertising your belief systems. How many people in your organization and community know what you stand for (beyond the initial interview/search committee)? How many constituents have repeatedly heard your values? Dan Rockwell of Leadership Freak writes: “You become what you repeat. Repetition is consistency. Consistency is predictability. Predictability is reliability. Reliability creates opportunity.”

From Core Exercise to Leadership Presence

Transparency involves so much more than listing the steps in our decision making process. Transparency, in its purest form, is exposing our souls to the communities that have entrusted us with their mission. (Hence, the connection to courage-ing!) Transparency is the act of allowing others to see who we are on the inside and get a deep understanding of what we stand for. Doing so will allow us to more comfortably make decisions within that belief system, to hold ourselves (and have others hold us) accountable to those values, and to inspire and rally our teams around those core beliefs. Our communities don’t expect everyone to agree with every decision we make, but they would hope that we are acting consistently with our consistently articulated beliefs.

When this seems really intimidating, let’s remember: We have not been hired simply for a job. We are the leaders and keepers of a mission. If our boards and search committees have done their due diligence, then they have most likely found someone whose personal values are the best match for the institution and community. They have appointed someone to bring the leadership presence the community deeply needs to thrive. It is urgent that we make decisions consistent with the leader they all met going in.

If we can become genuinely transparent, we can create our unique leadership presence. This is a spiritual presence, one where people know our beliefs and values and recognize that they reflect those of our institutions. This allows stakeholders to hold each other accountable to values that move the entire organization forward. We can then play a role to inspire and galvanize around the unique, spiritual energy that emanates from the “core” of the Jewish leader. When achieved, this is a highly spiritual experience, one that transcends our physical presence. After all, we can’t always be in the room.Hopefully, we are out, finally grabbing that well-deserved lunch.

Rabbi Yossi Kastan is head of school at Brauser Maimonides Academy in Hollywood, Florida. He is an alumnus of the Day School Leadership Training Institute (DSLTI) of the William Davidson Graduate School of Jewish Education of The Jewish Theological Seminary.

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