Former Head as Mentor: Why Pay for What We Can Get for Free?

Bob Kirkpatrick is an experienced leader in independent schools who over his 42-year career served in a number of roles, most recently as head of school for St. Stephen’s Episcopal School in Austin, Texas. Previous to his nine years at St. Stephen’s, he led Fox Chapel Country Day School in Pittsburgh, PA for seven years. Here he addresses an especially sensitive issue: Should a school’s retired head serve as a mentor to his successor?

Should the former, long-term (even beloved) Head of a School be retained as a mentor to the new Head? It’s a frequently asked question. Or it should be. Many schools confer that role to a retiring Head without thinking it through. Exit strategies that fashion an ongoing, formal, or informal role for the outgoing Head are not uncommon. But they are not always successful.

Among these roles for the outgoing Head is work in institutional advancement (in support of a campaign or in cultivation of long-term relationships with alumni, with whom the Head may have established strong ties over the years).

A more common role for the outgoing Head is service as a “mentor” or “coach” for the new Head.  This strategy can work, but there are dangers inherent in it.  For sure, there is a significant difference between a close, cordial relationship with a former Head, driven largely by a need defined by the incoming Head, and a relationship crafted by others (board, etc.), in which the new Head has little say or control. The essential questions a board and new Head must ask themselves before agreeing to some formal, continuing role by the outgoing Head as mentor are:

  •  Is this service something that the new Head wants and needs?

  • Can the focus of the outgoing Head’s support be completely on the success and well-being of the new Head?

  • Could the outgoing Head’s presence be at all a hindrance to the new Head’s identity as the school’s leader?

  • Are the presence and role of the outgoing Head clearly defined and communicated to the school community as part of a through, well-defined transition plan supported by both the Board and the new Head?

Engaging an outgoing, long-serving Head in a constructive, formal role as mentor to the incoming Head is not an insurmountable task, but it does bring with it several dangers, each of which poses a threat to the success of the new Head at precisely the time – the transition period – when he/she may be most vulnerable. They include:

  • making it more difficult for the new Head to establish his/her own leadership style and move forward with his/her (and the board's) agenda. Even the most fair-minded outgoing Head could be prone to protecting his legacy and ways of operating. It also invites comparisons between the two Heads, when the school and new Head need to be moving forward and focusing on what the new Head can offer;

  • increasing the risk of end-runs with the Board, creating confusion and even division over who's in charge, and possibly blurring lines of confidentiality with a "second Head" in the picture;

  • making it harder for the Board to give the new Head their full attention and support, which could lead to division and confusion over who should be the primary focus of their attention;

  • unwittingly discouraging the new Head from looking first to the Board for guidance and support and from expanding professional relationships and support networks (e.g., other school heads, professional organizations, other key members of the school community), instead mandating a formal relationship with the outgoing Head which could be a distraction;

  • overshadowing what we at TEG believe is better mentoring, by an objective third-party Executive Coach agreed upon by the Board and Head.

There are ways in which an outgoing Head can be a constructive force, aiding in a smooth transition by the new Head.

First and foremost, the Board and outgoing Head must be committed to serving the new person and to doing so with the full understanding and support of the new head.  The new Head’s success – and by extension the school’s – is what matters most.

The role of the former Head must also be clearly defined in such a way that the outgoing Head will assume a secondary, much less visible role and will express full, public support of the Board and new Head. To the extent that this is a formal role, with or without compensation for services, the plan must also include provision for the conclusion of this mentoring role. Again, for everyone at the school – including the outgoing Head – the only agenda is the empowerment and success of the new Head.

The outgoing and incoming Heads should meet on a regular basis early in the transition period, prior to the new Head’s arrival, but once the new Head arrives on campus, s/he should determine the need for more meetings.  At that point, the best possible scenario is for the two school leaders to develop an amicable, personal relationship that could continue for as long as desired or needed by both individuals. This friendship would be driven by mutual respect and and a common bond with the school they serve and with experiences they will have shared.

To be sure, long-serving Heads occupy a place of honor in the history of their schools and in the hearts of the people they leave behind.  Their contributions should be recognized, ideally in the last year of their headships. Just as the community looks forward to the arrival of the new Head, it should make possible one last “victory lap” by the outgoing Head, done in authentic, heartfelt ways. At that time the school ideally will be able to laud the best possible legacy of a long-serving school Head – that s/he left the school in a good place, contributed effectively to a smooth leadership transition, and helped to ensure the long-term success of the next Head of School.