leadership, headship, head of school, independent schools, search committees, candidates, attributes, learning, emotional intelligence, strategic thinking, execution, evaluation,

What I look for in Head of School Candidates

With thousands of books claiming to know the secret sauce of successful leadership, it feels overwhelming to distill all those critical attributes in an effort to predict a successful headship. To be sure, the alignment between the challenges of a particular school and the strengths of a candidate should be top of mind for every search committee, but consultants and search committees that focus on this alignment often ignore a more fundamental question: does the candidate have the baseline of leadership skills to be an effective head? Before a committee tackles the issue of “fit,” it needs to be sure that the candidate has the fundamental attributes of leadership to advance the mission of the school. The surfeit of leadership skills described in countless books and articles over the years prompts the question, “Which ones should be used in vetting head of school candidates?”

We could argue for years about what the most important attributes might be, which have the greatest value, and which best predict a successful headship. A persuasive case could be made for the following: self-awareness, transparency, and sound judgment. But none of these made my list below, not because they are unimportant, but rather because my experience as a head, a search consultant, and a mentor seem to resurface again and again the ones listed below. I present my distilled list, knowing that in order to have a practical, serviceable set of criteria, I am necessarily leaving out critical markers of leadership that may be equally valid. 

With this disclaimer front and center, here are the key qualities of leadership (in no order of importance) I look for in candidates I am vetting. 

1. Learning: Too many heads are satisfied with a superficial understanding of the challenges the school is facing and the way forward. Past experience from previous schools puts a stranglehold on creative thinking. Real learners ask questions and study data to understand the particular circumstances of the school they are heading. Yes, their experience may help them formulate good questions, but never do they let it be used in a rigid, lockstep way to formulate strategy. Learner-leaders don’t begin with answers; they begin with thoughtful questions. Moreover, I am looking for practical learners. In identifying viable heads of school, I want to see learning that leads to tangible results and value-creation. Finally, a proxy for learning is a degree of humility, a willingness to ask questions, learn from subordinates, and admit mistakes. 

2. Strategic Thinking: This attribute is probably the most difficult to identify in a candidate. Search consultants may think that because a candidate was involved in a strategic planning exercise, the candidate checks this box. Often, this is not the case. Thinking strategically should be a vital element in developing a strategic plan, but most independent school plans have nothing to do with strategy; nor do they reflect strategic thinking. Typically, the elements of a strategic plan consist of “things we should do because other schools are doing them.” Given this reality, how does the consultant and the search committee proceed? First, look for signs that the candidate mostly reverts to problem-solving mode. If this is the case, it probably means that her capacity to think strategically is limited. Second, determine if the candidate sees reality and understands clearly the capabilities of the school in achieving a significant goal. This is a vital skill in developing an achievable vision. Does the candidate understand the importance of talent, the necessity of structures, the centrality of culture, and the inevitable roadblocks that come with trying to achieve something great. Thirdly, can the candidate connect the dots within the school operation? Can she see the connection between program quality, teacher quality, market demand, fundraising capabilities, and more? Finally, is the candidate capable of diving into a change effort without a guarantee that the strategy will work? Belief is central to effective strategy; in fact, it motivates the candidate to prove her theory right. I look for a spark, a passion, and determination—markers (albeit, imperfect ones) that the candidate can be a practical dreamer. 

3. EQ (Emotional Intelligence): I feel certain readers will vigorously nod their heads in thinking about the importance of EQ in leading a school with multiple stakeholders. But I want to take a more nuanced stance on this attribute. I don’t think EQ means charisma or the person who can take over the room. In fact, too many search committees gravitate to candidates that have “winning personalities,” ignoring other critical aspects of leadership. EQ is more subtle. It involves engaging people in ways that create connections, helping navigate change efforts, engendering trust, which aids the leader in seeing more accurately the political landscape, and most importantly, capturing stakeholders’ attention. A head of school cannot be irrelevant. 

4. Execution: There are so many important management skills that it would be foolish to think a candidate could be outstanding in demonstrating all of them or even a small fraction. But there are some that I value more, and I am constantly on the look-out for them as I vet a candidate. The most important, by far, is attracting and retaining talent. Candidates receive gold stars if they reveal an understanding of the importance of talent. Secondly, is communication—the capacity to listen and understand as well as the clarity of their words both written and spoken. Thirdly, is the ability to calibrate the scope and pace of change, assessing accurately what is possible and what is not. And finally, is a drive to achieve, a competitive spirit. This attribute stokes confidence that the candidate will “figure it out” when faced with adversity. 

Although search committees have some responsibility for determining if a candidate has a baseline of leadership attributes, the consultant must shoulder the bulk of this work. Deep-dive interviews and preliminary reference-checking provide a rich treasure trove of evidence to determine the presence of these qualities. By assuming this responsibility, the consultant frees up the search committee to focus on “fit.” This one-two punch significantly increases the chances that the search will be successful. The high number of head transitions, including unplanned departures, suggests a more thoughtful approach to head of school searches is needed. It begins with an understanding of leadership, and applying the most important elements of that understanding to the evaluation of candidates.