Teachers and administrators take notice when a first-year head of school eats lunch with the same group of teachers and administrators at “the coaches’ table.” Within the first three months, a first-time head tackles what he sees as a major ethical issue, a long-standing practice involving several staff members. A new head decides to begin the strategic planning process in her first few months on the job. A rookie head, formerly an academic dean, reverts back to the familiar by visiting classes and writing up brief evaluations despite his claim that he is not doing evaluations. A new head relies almost exclusively on the advice of one senior administrator in his attempt to discern “faculty buzz.”

The above are variations of stories I have heard throughout my career, each one having negative consequences for the new head as well as the school. In some cases the negative reaction to these mistakes spelled the beginning of the end for the new head. These stories represent only a handful of “rookie” mistakes first-time heads make. Seen in isolation, they seem relatively harmless, but their negative impact can actually set the stage for a failed headship. Failing to understand that they are under a microscope, these new heads, through their actions, unwittingly begin creating a narrative that diminishes their political capital when, in fact, they should be intentionally building their capital.

First-time heads should be required to have an executive mentor, as there is an enormous difference between the job of senior administrator and the job of head of school. There is little in the way of experience that prepares senior administrators for the leadership challenges a new head faces. Regularly scheduled conversations between the new head and executive mentor can pull the head away from his or her natural predilection to revert to the familiar and instead, focus attention on strategic thinking and adding value to the school. In addition, the executive mentor is available for counsel on thorny problems every first-year head faces. Finally, the executive mentor, if need be, can take the pulse of the community by doing an abbreviated evaluation mid-year, sharing the results only with the head. In this way, the head can make changes before the more formal board evaluation at the end of the year.

In order for a mentoring relationship to be successful, it is imperative that the mentor be a former, successful head of school. Being a head of school is extremely challenging and complex, requiring a depth and breadth of knowledge and skills. Only someone who has successfully done this job can provide the practical counsel to help a new head make good decisions. Moreover, it is critical that the mentor work only for the head of school in order to ensure a foundation of trust. The mentor should have one agenda only- the success of the head of school.

The beginning of a new head’s tenure, in most cases, should focus on two objectives: 1) deeply understand the mission, identity, and culture of the school and its place in the marketplace of schools against which it competes, and 2) build political capital and a brand that engenders confidence and trust with all of the key constituencies. Achieving these two objectives requires planning and discipline. The right executive mentor can help the new head keep his or her “eyes on the prize,” setting the stage for a successful headship.