When a New Head Succeeds a Legend

In his 42 years in independent schools, Dave Davies has served as head of the Deerfield-Windsor School (GA); a “founding” upper school head; an interim head; and a 27-year veteran of boarding school life. Here he addresses the challenges faced by a new Head succeeding a legendary school leader.

A legendary Head of School retires, the school celebrates a long, successful tenure, and the community approaches the transition with great trepidation. Why? Because the retiring Head plans to remain in the area and pledges to make her/himself available to ensure a smooth transition and the continuation of the school’s momentum. That sounds like a perfect solution, but in fact, it can be fraught with peril for the next Head, especially if s/he is a first-time Head.

Examples abound where the former Head’s presence on campus or in town has enabled back-channel communication from parents, faculty, and Board members. Even if the retired Head has the best of intentions, his/her accessibility in the community makes keeping an appropriate distance very challenging. “Trouble” does not require criticism or negative comments from the former Head; sometimes anything short of a ringing endorsement of the new school leader will be interpreted by an eager critic as tacit agreement. Indeed, even a seemingly benign conversation about the new Head can be misconstrued by his/her critics.

What to do? Several schools, in an effort to be helpful to the incoming Head, have given the retiree a position at the school, perhaps in advancement, and an office on campus to provide ready access for the new Head for coaching, mentoring, or just a “quick question.” That way the retired Head appears and in fact is “on board.” That approach appears to make sense, but it can lead to unintended consequences.

For example, in at least two cases that I know, when the new Head struggled, the former Head was just too conveniently on the scene to assume an interim Headship. In these cases, neither former Head was angling to have his/her position back. However, rather than fully supporting and working with the new Head in facing the most difficult challenges together, the Board appeared to have chosen a convenient solution and employed a quick “hook” when concerns arose.

There is wisdom in the “cold turkey” practice observed by several religious denominations where the previous priest/minister may not visit the former church or even associate with parishioners for at least a year after departing. One good priest friend told me that when the child of best friends asked him to perform her wedding, he agreed to do so, but not at his previous church. This practice gives the new cleric the space to develop relationships, find her/his style and voice, and begin a new direction.

But the question looms – “Why would a school possibly waste all of a successful Head’s insight, connections, expertise, and goodwill in the community?” Wouldn’t s/he be able to help the new Head avoid landmines and swamps and accelerate the development of relationships with key stakeholders? And, after all, the retired head plans to remain in town, where s/he has lots of friends. S/he isn’t going to disappear!

The solution lies somewhere between an on-site office and a year’s “exile,” and the key is for the new Head to be the initiator: Begin by inviting the former Head to a series of off-campus lunch meetings, at first just casual, personal, “get acquainted” interactions. Then, perhaps jointly the two can develop an agenda for future meetings. If the new Head is comfortable doing so, s/he could invite the former Head to a few major school events such as graduation to demonstrate publicly their working relationship.

Of course, ideally, that relationship can (and probably should) begin to develop as soon as the new Head is named, and before his/her arrival on campus. Phone or Zoom meetings and e-mail correspondence are easy. If distance is not an impediment, and if the search committee or Board funds a few visits to the campus for the incoming Head (they should, if at all possible), a dinner with the current Head and spouse/partner, if possible, would be a great ice-breaker.

Of course, before all of this happens, the retiring head should regard his/her “lasting” legacy to be not only the state of the school that the new head inherits and but also the success of the new head. In that regard, by tackling some knotty problems at the end of his tenure, the “old” head can help to pave the way for the new head: budget headaches, personnel issues, legal problems, etc. The fewer controversies the new head inherits, the better. What is more, a highly regarded “old” head can address such challenging issues with far less fallout than the new head can. Also, the “old” head should assemble the material s/he will pass on to the new head in formally transferring leadership of the school. Again, the goal is a smooth transition that prepares the new head for success.

Most importantly, the Board, in concert with the new Head, should carefully define the role of the former Head and make that clear to all parties. The Board should also be particularly attuned to any interference, lack of support, or negative overtures from the former Head. Either the Board Chair or another current or former member of the Board close to the previous Head should then gently confront her/him and solicit support. Separation from a life that was both consuming and rewarding is challenging. Some former Heads find any changes to “their program” or their school’s “Way” to be an affront, and some don’t sit quietly by to see programs, traditions, or styles that were near and dear to them go away. Again, Board members should be especially tuned in to such negative “vibes.”

Furthermore, Board members should not abide by any approaches from faculty or parents that compare the new Head to the previous one. “Public praising and private criticism” is imperative, especially in the first year or two. The Board Chair is well advised to remind Board members that there are no individual Board voices in the public square; the Board should speak only as a unified whole.

Thankfully, there are many more opportunities for the new Head and the previous leader to establish solid, mutually respectful relationships for the good of the school. Cases where the new and former Heads meet together with significant members of the school and local communities, successfully make development calls together, and present a united front are not only pleasant but beneficial to the school.

Clear, respectful communication and appropriate distance can ensure a constructive relationship between the two leaders for the good of the institution.