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7 Pitfalls of Searching for a New Head of School


by Rabbi Maccabee Avishur

I was recently on a call with the board president of a Jewish school who is considering conducting a Head of School search sometime in the near future. She asked me a great question: What are some of the pitfalls that we should think about when searching for a Head of School? Here are the top seven pitfalls we’ve observed in our work supporting schools as they search for new Heads.

1. Thinking you have more time than you do.

The ideal time to begin a Head of School search is somewhere around 18 months before you’ll need a new Head of School. That sounds like an eternity, but this is the best length of time to allocate for two reasons. One: The next Head of School you are going to hire is probably happily employed at another school (or at another job). That person will need to begin planning very early in the school year to adequately help his or her current school prepare for a leadership change. Two: Starting that early improves your chances of ending your search with a positive result within the timeframe you’ve identified. If you start later, let’s say within 12 months from when you’ll need the new Head to start (a common starting point), finding a Head of School for the fall will be more difficult. You may need to engage in a second year of searching while an interim Head helps keep the school running. Many schools probably have trouble conceiving of how they could possibly know that they’ll need a new Head of School a year and a half in advance. Open and transparent discussions with your current Head can help determine how long that person plans to stay in the role and can help your school prepare for any upcoming transition.

2. Thinking the field is bigger than it is.

Because you have so many wonderful educators in your school, you could reasonably assume that there are dozens if not hundreds of qualified candidates out there waiting to apply to lead your school. Sadly, that’s not true. The number of qualified candidates who are open to considering headship is small. The number willing to relocate in order to lead is even smaller. You may get lots of applications, perhaps even close to 100; however, it is likely that most of those applicants will lack the qualifications, experience, or training that you’re looking for. The number of truly qualified candidates is likely to be between five and ten. Furthermore, many schools would like to hire a Head of School with previous Head experience, with good reason. After all, the best predictor of future success is past success. However, if the field of potential candidates is already small, the field of experienced Heads looking to make a lateral move is tiny. We encourage schools to take a broader view of experience, including candidates who have significant experience in supporting roles in school leadership. For example, a successful division principal who is ready for the next challenge often has much of the knowledge, skills, and experience to be a strong Head of School. That person may be a wise choice for your school, especially if you are invested in providing ongoing support and training to your new Head.

3. Expecting to hire the Messiah (or a “Superstar”).

Your school deserves an amazing leader, and there are amazing leaders in our field, but thinking in terms of “superstar” or “rock star” is likely to leave you disappointed. Today’s Head of School is often expected to fill many roles: lead educator, Judaic scholar, spiritual leader, fundraiser, public relations expert, recruiter (of staff and students), supervisor, business manager, and counselor. It is seldom true that any one candidate is outstanding in every area, and every candidate you interview will have strengths and deficits. Your search committee should think about the two or three roles or traits that are absolutely critical for your Head of School’s success and then be prepared to address the deficits that each candidate will bring to the job. Many deficits can be remedied fairly quickly through coaching and training, while others take more time. Some qualities (especially personality traits) are a bit harder to shift. Identify those you won’t compromise on and those you can live without or remediate. Just remember throughout the search that it’s neither likely nor fair to expect your candidates to be an impossible combination of traits. Another word of caution: You may adore the current Head who is leaving, but be careful about wanting to replicate that Head’s qualities. When you hired your current Head, the school was in a very different place than it is now. Hiring someone who is different from your current Head is not a betrayal; you are planning for a successful future and want to find the right leader for this particular time in your school’s history.

4. Not planning properly for the future by creating strategic priorities and expectations.

Too many schools hire new Heads without giving them a clear sense of their priorities and expectations, instead holding tacit expectations that your new Head is unlikely to meet. Assess what you think the school will need in the next three to five years and create a manageable list of strategic priorities based on these needs (this is a job for your board). Then, identify the skills, experiences, and dispositions you believe the next Head will need to lead the charge in this direction. Not engaging in this strategic prioritization can lead to frustration and dissatisfaction for both the board and the new Head, and often ends in the termination of the Head after a short tenure. Investing in planning for the future now will increase the likelihood of a long-term and positive relationship with your new Head. And remember that the Head of School shouldn’t be expected to bear the burden of leading the school alone. The headship is a partnership, and the new Head will need partners on the board and on the staff. Think about these partnerships as you learn about your candidates and as you build the systems that will support the new Head’s success.

5. Inviting too many people to serve on the search committee and NOT inviting the right people.

You want to convene a search committee that is representative of the various stakeholders in your school, but small enough that you’re able to remain nimble. The right size is about seven to eight people — much larger and you’ll face scheduling and other issues that will undermine your committee’s real purpose. Your search committee should include representatives from your executive board, your board at-large, parents who are not on the board, and faculty. Many schools balk at including faculty, but their presence on your search committee has a lot of advantages, including access to faculty perspective and faculty buy-in. You can include other stakeholder groups as well, but these are the core constituencies whom we think should be represented.

6. Not embracing transparency.

In the past, the Head of School search was conducted in secrecy. One former board chair described it this way: A bunch of school “machers” who gathered in a smoke-filled room would handpick their new leader with little process and even less transparency. Faculty, staff, parents, and other important stakeholders were often excluded from the process until the very end when the newly hired Head of School was brought to campus to be shown around. Sometimes these placements worked out, but often they failed. The new Head of School, no matter how talented, often faced a hostile faculty and parent body who felt excluded from the process and, therefore, probably subconsciously, engaged in behaviors that undermined the new Head’s chances of success. Think about what you have to gain by embracing a fully transparent process. The more stakeholders you bring into the process, the more likely you are to have their buy-in and support as the new Head transitions into your school. We especially recommend arranging for your two or three finalists to visit your school for a fully public visit to see the school in action, meet with faculty, staff, students, parents, and other important stakeholders, and to let them learn about your school. This is also an important opportunity for your search committee to see the candidates interact with your stakeholders. The insights you gather and other feedback will add color and nuance to everything you’ve learned about your candidates during the interviews.

7. Thinking that because you have been involved in hiring in your professional life, you know how to hire a Head of School.

Every search committee I’ve worked with has included people who have done some (or a lot) of hiring in their professional lives. In fact, some search committees have even included people with experience as executive recruiters. All that experience is valuable and should be brought to bear in the Head of School search. At the same time, searching for a Head of a Jewish day school is a unique enterprise that requires a unique approach. What made people successful in their previous hiring experiences may not translate to your Head of School search.

Closing Words

The Head of School search process is full of twists and turns. Knowing these pitfalls in advance and preparing to address them can help lead to a healthier search and better outcome. Contact Rabbi Maccabee Avishur or Jill Kessler at Prizmah to learn how we can support you and your school.