Deborah is the head of school at Milton Gottesman Jewish Day School of the Nation's Capital in Washington, DC.

From Survival to “Thrival”: Empowering Leadership Teams

I am no expert on sustainable headship, at least in terms of years. I began my tenure in July 2020, so I’m just getting ready to sign my second contract. But considering the intensity of my first couple of years (I count them in dog years), I had to quickly develop survival strategies. 

Sustaining my school, my team, my family and myself through that time was the hardest work I have ever done. That early experience helped me recognize the many levels on which the headship could yield a fight or flight response. Purely by necessity, I set out to build a sustainable system to survive the early years of my leadership—with the hopes of moving from survival into “thrival” mode in the next few years.

One of the most challenging parts of the role that can come as a surprise is the psychological weight that heads carry. The workload is heavy, the inbox always seems to refill, and the number of meetings packed into a day (or night) boggles the mind. But most people who are used to hard work are up for those challenges. It’s the mental load—the sense of ultimate responsibility—that weighs so heavily and, to my mind, accounts for the short tenure of most heads.

My approach to this has been an amplification of my general philosophy, which is to work with and hire extraordinary people and to truly empower and support them. Coming into a new workplace and culture mid-crisis made it challenging to demonstrate my commitment to empowerment at all levels of the organization, but it means that I can now more clearly articulate what needs to be true for this leadership approach to work. 
I believe there are at least four key elements to its success.

Shared Vision

First, there needs to be a shared vision between the head of school and members of her leadership team. I don’t mean that the head shares the vision and everyone listens, nods and takes notes. Rather, the vision needs to be shared on an elemental level—in our bones and kishkes—that develops organically through deep relationships and a shared orientation and philosophy. 

To be clear, this is about big picture vision, not the granular. In fact, if the head has a very detailed and exact picture of what they need their school and program to look like, this can be a major impediment. When you have a shared big vision, that still allows for many smaller choices and directions—but the leader has to be comfortable with any of those outcomes to have a truly empowered team.

Shared Standards of Excellence

The shared vision must be accompanied by shared standards and expectations of excellence. If you are aligned philosophically but not qualitatively, struggles and frustrations will develop on that front. Unlike shared vision, which is more innate or organic, these standards can be formulated and workshopped as long as the head and team have the ambition and stamina to consistently meet them. 

In order to authentically develop these communal norms and expectations, early on the head has to be prepared to allow some (lower stakes) things to not meet the highest expectations of excellence. Those programs can then be used to calmly reflect—with an individual or a team—on why they did not rise to the level they should have. The team will learn more and more quickly by doing, and falling short a few times, than by being told exactly how to execute every step of a perfect event. To be explicit, a leader of an empowered team cannot be punitive or angry about such low-grade missteps; it’s part of the deal.

Delegation vs. Empowerment

Intentionally allowing small mistakes requires the leader to exercise restraint strategically early on, not to always step in to fix and not to get upset if things don’t go perfectly. This is one of the many short-term vs. long-term trade-offs leaders need to make every day. A misstep in the short-term must be seen as an opportunity for reflective practice and growth, and for the evolution of shared standards of excellence in the long-term. It’s worth it! 

If heads can’t restrain themselves from intervening in everything and being punitive about mistakes, they run the risk of creating a culture of delegation, which is dramatically different from empowerment. With delegation, the leader continues to be accountable for every detail, even if they aren’t executing them. This has two major downsides. First, the team members don’t feel empowered, which is a hit to their sense of growth and trust (and therefore retention) in the workplace. Second, to my mind, delegation is also a major source of the mental load that so many leaders carry, and moving away from it is one of the keys to sustainable leadership. Trust your team—which shares a vision and high expectations—to figure out the details in their area of expertise.

Seeking Support

Knowing that your team members know when to seek support is a critical element of an empowerment culture. The leader can only comfortably and confidently let their team members fly if they know they won’t be shy about seeking advice and backing, or sharing when things aren’t going well. We all need that support, and being vulnerable enough to visibly model seeking it (from mentors, board members, and the team) communicates that this too is an essential part of the supported empowerment model. 

I try to live and lead authentically by this approach each day. Honestly, it’s the only way I know how to work and get the job done. To be fully transparent—and so my team doesn’t giggle behind my back about the exception that proves the rule—I simply cannot yet fully empower when it comes to the food we serve to our staff. This may come from being a vegetarian at one too many kosher events, being morally opposed to mayonnaise-based meals, or recognizing that this is a crucial way we can show appreciation to our team during tough times. In any case, I own (and joke about) that this this is a place where I struggle to hew to my own approach; I think it’s important that we know and share our empowerment weak spots. 

My plan now is to judge my own sustainability in this job not by the number of years served, but by the number of meals served—without my controlling the menu.