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Being a Head of School (HoS) isn’t easy. After all, today’s Heads are charged with creating and maintaining relationships with the teachers, students, parents, and board members; engaging in donor relations; and ensuring academic excellence, all while providing strong leadership. But coaches can help strengthen that leadership and empower a HoS to build his or her capacity for problem-solving and strengthening the school on every level.

We spoke with Jane Taubenfeld Cohen, Prizmah’s VP of School Services, who served as a HoS for 22 years before becoming a coach, about the challenges that HoS face today and the power coaching has to alleviate those challenges.

“The demands of the [HoS] job have grown tremendously,” Cohen said. “They have to do fundraising and work with the board and the parents and be the instructional leader of the school. Essentially, the HoS is the CEO, who has to run the business side and have people report to him or her.”

According to Cohen, today’s parents expect more from school leaders than ever before, and those expectations are just the tip of the iceberg. “The affordability of day schools in general has become a big issue — recruitment, retention, and cost of school is a huge pressure. A lot of school leaders are being judged by how many students are in the school. At the end of the day, a school’s budget is dependent on how many students [there are].” Availability and responsiveness is another area that Heads of School grapple with as many report an expectation that they will immediately respond to every email and question.

With all these pressures, it’s not uncommon for school leaders to feel completely alone. However, Cohen says that coaching helps a HoS shift their perspectives to understand that they’re not in it alone. Employing strategies like reporting in a transparent and open way with the Board of Directors and enlisting others to be partners in the work often works wonders in mitigating the pressure. “This is not going to solve the affordability problem, but the fiduciary responsibility comes from the Board of Directors. I often partner with Heads of School in starting by building a relationship with the Board president so they can work through these challenges together.”

Coaching achieves a lot of things, but there is one thing that it does not do; coaching is not about telling clients what to do. Cohen notes that it’s mostly about “asking good questions, building the leader’s capacity to reflect on his or her own leadership, and sharing wisdom from the leadership and Jewish field.”

Another misconception about coaching is that it is exclusively for new leaders. While at least half of Cohen’s clients are in their first five years of work, her clientele spans ages and experiences. In fact, she has one client who has more than 20 years of experience.

Cohen is quick to point out that coaching success is directly related to the coachee’s level of commitment. “Like every other thing, it’s really about you and the amount of time effort and reflection you put into it. The job of the coach is to ask really good questions more than anything else, so that the person gets to a place that’s good for him or her. I’m not trying to recreate the way I would have led over and over again. It matters more what people hear than what coaches say.”

During her coaching experience, Cohen learned that showing her own vulnerability has been a helpful tool. “People feel better, knowing that other people struggle and yet still continue to lead. This knowledge helps them feel more willing to admit their own vulnerabilities and persevering through what’s hard.” It’s also important to note that coaching isn’t about weakness — Cohen’s clients are strong and exceptional leaders already. “Through coaching, [we say], let’s help this person be a model for his or her faculty that growth is built into leadership.’”

There is no magic formula that a coach follows. Coaching is by nature very individualized to the needs of the client. “It’s similar to what is true in good education,” she said. “Understand the individual you’re coaching and build from there. It’s my job to figure out where that person is and where that person can grow.”