Succession Planning to Set Schools Up for Long-Term Success

Spring 2024

By André Withers

This article appeared as "Down the Line" in the Spring 2024 issue of Independent School.

In the spring of 2021, Dan Vorenberg, head of school at Mirman School (CA), began a purposeful conversation with the board chair about his plans to retire at the end of the 2023–2024 school year. Vorenberg, who has led independent schools for more than 22 years, including 11 years at Mirman, explained: “I was entering my 42nd year in education. I had a specific set of markers I had hoped to achieve at Mirman, which I did. I felt no pressure to leave and had plenty of energy, but I felt that the organization had benefited from my specific skillset and needed to grow in areas that weren’t necessarily my strengths. Put another way, I think I could have stayed longer, but I really felt the school was moving forward with vigor—and like most things in education, you kind of want to get going when things are at their best.”

Vorenberg will be joining the growing ranks of heads leaving the profession, and his board will be among those who will need to navigate the planned or sudden departure of their leader. Over the past five years, head of school tenure has seen a remarkable compression; the average tenure, according to recent NAIS data, has fallen from 8.4 years in 2017–2018 to 7.3 in 2022–2023. Simultaneously, a growing number of independent schools are grappling with the specter of turbulence, with more and more outside forces impacting how schools are run and, in some dire cases, forcing leaders out or even forcing schools to close. In the face of this educational maelstrom, one glaring truth has emerged: Securing exceptional leadership for schools is more challenging and more essential than ever before. 

As schools find themselves at a crossroads, a paradox emerges: Hiring a new head of school has become—to all appearances—easy, but crafting an effective and creative succession plan has never been more arduous—or crucial. It is no longer sufficient to merely recruit and hire; it is now imperative to set a table of mitigation, cultivation, and planning. Succession planning, once viewed as a behind-the-scenes board chore, has moved to the forefront of exceptional governance. Boards need to recognize that shorter tenures are a reality and that their succession planning needs to be shaped around the research-based reasons that heads of school are barreling toward shorter tenures or departing the profession altogether.

Push and Pull 

The head of school role has changed dramatically and rapidly over the years. At one time, the head of school was the master educator. Lately, the role is less chief education officer and more chief executive officer. The role has become far more focused on operations, financials, and risk management—prompting much disillusionment for gifted educators who ascend the ranks only to be met by external headwinds and changes that don’t reflect the internal work done in their professional climb.

NAIS’s 2023 “Hot Issues Survey” explores the most pressing demands heads are grappling with, some of which are enduring challenges that have taken on new dimensions, including finding and retaining qualified staff as workplace expectations shift, responding to conflict in and about independent schools, caring for staff and students during stressful times, and balancing demand for more programs with available resources and initiatives. In addition to the fundamental changes in the role and demands of the position, head of school departures are being prompted by a few other major factors: the long wake of COVID resulting in either exhaustion or spent emotional capital; heads’ sense that their strategic vision has been fulfilled; and a rocky head-board relationship. 

Fortunately, the powerful and purpose-driven elements that drew so many school leaders to their posts do still exist. At the top of that list is the necessary and rewarding work of educating and being in community with children. Knowing that there is great potential for making a positive impact on the lives of young people is a powerful draw. The chance to shape and pursue a vision for education is another; natural leaders are naturally curious and feel compelled to find a path toward manifesting that vision. The lifelong learning tenet at the heart of so many of our schools also goes hand in hand with the pursuit of leadership. 

But as tenures shrink and the push factors grow stronger, boards are called to be intentional and creative in preparing for the inevitable. 

Planning vs. Search

Boards often make the mistake of not having a clear succession plan in place before a leadership vacancy arises. Without a preestablished plan, they may struggle to prepare themselves and the community, leading to tumult or increased anxiety about continuity. And they may begin by jumping right into a search process. 

As search consultants, we like to ask, “What’s the current succession plan that the board is executing?” Many times, there isn’t one. In the absence of a succession plan, the work of the search consultant begins with deep and voluminous conversations with the board about the state of the school. This information is usually shared in the form of anecdotes and a variety of documentation that paint a picture of the health and viability of the school. 

And while the standard search process has historically yielded success—formal succession plan or not—boards will be better served by taking steps to ensure that they aren’t inadvertently being short-sighted or making the search process more potentially disruptive for the community. A search for a new leader is a procedural and emotional process. Thoughtful succession planning leads to the community feeling confident in the process, excited by the candidates put before them, secure in the choice ultimately made, and optimistic about the first year of the new head’s tenure and beyond.

To prepare for a leadership transition of any kind—planned or sudden—boards must take the leadership landscape into consideration in developing an effective succession plan.

Use succession planning as an exercise of calibration. A forward-looking board will see the inevitable transition from one leader to another as a time for adjusting various relationships or dynamics within the community—including the proverbial “pendulum swing” that occurs when there is a groundswell to drastically counter the style, temperament, or vision of the previous leader. A more thoughtful approach is to establish a mechanism to gauge and service the needs of the community beyond a climate survey, to fine-tune the board partnership and even its makeup, to readjust the interface with alumni. For example, is there someone within the community who can play an “ombudsman” role—someone whose primary (short-term) task is to listen to various community stakeholders and convey the issues that were top of mind? This information helps validate or invalidate assumptions about the state of the community and can help ensure that the board is focused on and talking about the right things.

Leverage the administrative team. Admin teams are critical to head transitions, given the stability that their continuation in their roles creates as well as their participation in the interview process. However, there is tremendous value in engaging them in a more formal knowledge transfer that includes an institutional “download” for the board—and for the head-elect—that would, over time, provide an invaluable chronicle of “from where we’ve come.” For the board, this exercise would not only provide insight into what the team is looking for in the next leader but also identify the operational priorities. Having senior leaders conduct a documented leadership audit (skills, length of tenure, portfolio, special roles, retirement window, years-out data) at the onset of the search or as an ongoing exercise would be useful before and during a leadership search. 

Develop a reflective process. Viewing a head transition as a time to calibrate goes hand in hand with reflection, and boards must become practiced in using reflection as a tool. Here are some critical questions for board reflection: What has served us and the outgoing head of school well and what hasn’t? How would/do we adjust for a new leader with a new profile? How might we need to position ourselves as different challenges arise? 

Board self-evaluations are also a critical piece of this work and should be referenced in board work throughout the year, not just at the end of the year or only at the point of leadership transition. These evaluations are very useful to share with a search consultant and even the finalists during a search, but they are even more useful when they are referenced in the context of routine meetings and times of generative thinking.

Design a search strategy, not a search processOne of the aspects most associated with a head of school search is haste. And while there is certainly an important time element, there is wisdom in responding to the leadership change rather than reacting to it. Far too many schools look to develop a search process rather than working with a search consultant to build a search strategy. Strategy means making an integrated set of choices that collectively position the school to yield their desired results. Process refers to the steps taken to achieve a particular or tactical goal—it’s the how of achieving success, while strategy is the what and why. Both are needed at various times for various reasons, but if the transition is going to be more than transactional, strategy is necessary. With a clear strategy, schools will have resounding holistic results that may very well lead to a more satisfied community and a lengthier tenure for the head-elect.

Working With the Headwinds

One thing that becomes abundantly clear from discussions with heads of school and board chairs is that the work of cultivating a lengthy tenure for a head of school is becoming harder. And amidst the reality of more frequent leadership changes, not only does succession planning become even more critical, it’s also important to consider fresh approaches at the board level to manage the headwinds appropriately.

Refocus the work of the head support and evaluation committee. Whether it’s head transition or setting the budget, a dynamic board is critical. The issues schools are facing today are so varied, so frequent, so volatile—and so important to get right. For that reason, the boards of today can’t be the boards of yesterday. Similarly, the challenges that boards face in hiring and retaining their sole employee are just as varied and important to get right. So, if we know this to be true, boards should consider how they’re built and what their full and committee goals are to align with those push factors and help mitigate the things that are pushing heads out. For example, the committee on trustees could consider inviting an educator to serve on the board as a way to provide perspective and support to the head of school. And the board should ask the head to speak specifically to the areas of challenge as part of the head’s report to ensure that these challenges are top of mind for the full board. 

Develop a “talent team” within the board structure. Such a team would be responsible for an ongoing talent inventory of the board and the senior leadership team, and the school’s strategy for investing in professional growth. By having a dedicated team or task force with a holistic approach to leadership development and succession, the school can consistently capture the talent, experience, and capabilities of its top leaders and be better prepared for transitions while maintaining stability and continuity.

Conduct a succession simulation. Organize succession simulation exercises at the board and senior admin level in which the full leadership teams practice real-life leadership scenarios to hone their capabilities, decision-making skills, and adaptability. The board then is not unfamiliar with a planned or an unplanned departure. This would mirror some of the emergency preparedness exercises school leaders do on a routine basis. A board might discuss and practice what would happen during an abrupt departure, such as a firing or a death, as a way to help the board think about how to communicate the issue, care for the community, and deal with any financial ramifications. 

Consider creating an admin-in-residence role. One of the things heads of school say make the job difficult has to do with bandwidth—theirs and that of their direct reports. There is simply a lot of work involved in doing the business of school. Combined with that, the constant need—from everyone in the community—for access to and input from the head of school makes it even more challenging. 

Bringing in a seasoned administrator or consultant to serve as an admin-in-residence could be a lifeline for the head. Someone who is immersed in the life of the school (but not permanent or a direct report) could divert some of the constant need for access, coach others in being self-sufficient in their leadership capacity, and provide a sounding board. For example, this might look like setting up a regular schedule where a consultant is on-site to serve as an administrative and leadership resource who supports tasks like strategic planning, tending to the administrative team, integrating new personnel, and coaching teams and division directors. 

Planning for Tenure

Every student wins when there is a great teacher in the room. Similarly, every community wins with a great leader at the helm. Although there are an increasing number of things that make leadership unattractive and make investing in a long tenure untenable, knowing what those challenges are and answering with bold creativity and new approaches to succession planning can help boards create a healthy community—and perhaps ultimately make lengthier tenure the norm in an era rife with change and decreasing tenure. 

Questions for Boards

Whether or not a school is navigating a head of school departure, the board should keep succession planning at the forefront. Here are some questions that should be part of ongoing board work and discussion:

  • What’s been our attention to or frequency of board-level discussion on succession planning?
  • Is succession planning aligned with other institutional priorities? 
  • Is succession planning a transparent piece of information?
  • Is this a time to update or reimagine the head evaluation tool? 
  • Are there patterns or corollaries between the board self-eval and the head-of-school eval?
  • What risks do we face when our head leaves or resigns?
  • What will the impact of a head of school turnover be?
  • Will we need an interim leader? Who can/should fill that role?
  • Can we cross-train staff to delegate certain duties temporarily?
  • How do we fill any leadership gaps?
  • What leadership needs does the organization have?
  • Are our hiring and onboarding processes sufficient for a quick succession?

A Head's Perspective

Dan Vorenberg, head of school at Mirman School (CA), announced that he’ll be stepping down from his role at the end of June 2024. He has been in education for more than 40 years and has served as a head at independent schools, including Mirman, for more than 22 years. His experience has afforded him a longitudinal view of how schools have and have not planned effectively for leadership departures. In this Q&A, he reflects on his two-year off-ramp process. 

André Withers: Before your announcement of your intention to retire, what was the board’s approach to succession planning?

Dan Vorenberg: I’m not sure the board was specifically intentional about succession planning. But I do think my board chair may have been alluding to succession planning when he continually challenged our trustees by saying, “One of our most important goals should be to make the headship of Mirman the most attractive opportunity out there,” even though I was still seated. I thought that was visionary and the highest level of board stewardship. 

AW: Was there any consideration to hiring from within for your successor? 

DV: There was some, and I know the board would have welcomed an internal candidate, but the individuals who might have been candidates made—what I deemed were wise—decisions to continue to serve the school in their current capacity. I am highly confident that there are two or three folks that will, should they choose this path, be heads of school one day.

AW: Having seen a number of heads retire or move on from their headship, what did you want to avoid? 

DV: Well, I really didn’t think being fired sounded like fun. I have only recently just begun to talk to heads who’ve retired. Many of my friends and contacts have either tried interims or joined consulting firms or taken a break altogether. I think the biggest pitfall I am trying to avoid is giving into my own anxiety about actually “not working” for a moment. I worry this might manifest itself in snagging the first thing that comes along. Rather, I think it’s so important that reflection and personal introspection be the driver for essentially “what’s next.” I think time for this is essential regardless of role or stage of life, but perhaps never more so than when between chapters of one’s lived narrative.

AW: How have board meetings and operations been different since you announced your retirement? 

DV: I can’t overstate the power of a plan that is internalized, where appropriate, by all constituents. There were public letters and meetings, Q&As with consultants, and very regular and open opportunities to both survey and embrace the community in ensuring that all voices mattered and that trust between and among the school leadership was modeled and messaged.

AW: How did you and the board set the transition up in such a way that people celebrated the good rather than anticipated tumult?

DV: Well, it has been a great run, and it hasn’t been without tumult. There was self-generated tumult as I moved quickly—perhaps, upon reflection, too quickly—when I arrived. There was also inexorable movement forward on powerful initiatives that have strengthened the school’s reputation, program, and identity. I really believe that if you can align good and wise governance with the operational side of the school, then departure announcements, war, and pandemics really won’t throw the organization into chaos. Dynamic schools see transitions as opportunities, and tumult simply serves as an affirmation that the foundational aspects of the organization may not have been as sturdy as one would hope.

André Withers

André Withers is a partner at Educators Collaborative, a search and strategy firm. He has worked in independent schools for 26 years and was most recently assistant head of school at The Madeira School in McLean, Virginia.