The Headship Paradox

When Jeff Paulson, CEO of the Academy for International School Heads, sent me three questions and asked me to write this article, I was pretty skeptical. There are a million Heads’ leadership blogs (including mine) and LinkedIn posts about this sort of thing, and besides, answering these three prompts required me to be a little more personal than my usual style. Which is in itself quite an interesting point - I generally feel comfortable writing as a Head of School, with a somewhat institutional voice; and this piece is something different; what do I, Nick the human being, think about the role of Head of School? 

There is a personal / professional blur here, and it feels slightly self-indulgent to write from a personal, rather than professional perspective. And it’s rather exposing, even; I worry that a positive approach will come across as self-aggrandizing; and a negative one as self-pitying. And as there are, of course, both positive and negative things to say, this did not bode well for an article! But in fact, chewing this over with a friend made me realize that this tension is in itself indicative of something very interesting - that for me, the biggest demand of the Head of School role is that it requires diametrically opposed, even contradictory, approaches on an ongoing basis. So having mentioned the personal-professional tension, I’ll outline a few other tensions and then turn to two ways to manage them.

Being Symbolic and Substantive  

Heads serve as the face of the school (a close colleague uses the term “spiritual leader”). It is vital for Heads to embody and project a school’s values, vision, and ethos - and by its nature, this symbolic aspect should be very visible. At the same time the substantive side demands a deep engagement with the practical and operational facets of running a school - which are likely far less visible. So Heads need to both project big-picture statesmanship and also engage in the intricate, day-to-day realities that sustain a school community (the complexity of the latter may vary according to institution - in my current school of 6000 students I find it really very challenging). Perhaps more than for other tensions listed here, these two elements can be made to operate in synergy, so that values really do infuse the daily operations of a school. But it’s easy for good communicators (and most Heads are that) to be seduced by the symbolic parts of the job - speeches, conferences, networking, dare I say writing in various publications?  - and other public appearances. These Heads might say they “need to remain strategic”  or that they “leave the details to others” or “externally focussed.”  I have seen this, and it is, in my view, a profoundly mistaken approach. Interestingly, symbolic capacity is fairly easily assessed at interviews, substantive capacity far less so. This limitation of interview processes is why Head appointments can be so drawn out, and so many appointments fail.

Being Absolutely Fair and Sensitive to Individual Circumstances  

Heads will know that any perceived injustice - say an outlier contract, unusual leave arrangements or apparent discrepancies between disciplinary processes - will likely result in accusations of favoritism or unfairness. Heads will also know that applying policy rigidly does not allow for contextual adjustment to allow for individual circumstances, which can be extreme and heartbreaking. So this tension is about upholding rules and demonstrating empathy without appearing arbitrary or disconnected. There is absolutely no escape from this one, because every institution needs policies, and behind every policy are real people with distinct stories and needs.

Being Resolute and Open-Minded 

These are both highly desirable qualities, but they can get in the way of each other. It’s obvious that no-one wants a Head who is determined on a course of action, regardless of input and context. I am thinking of the danger of the single-minded pursuit of some brilliant curriculum initiative or staffing notion that was so successful in a different school. At the same time, a Head needs the courage to stay the course in a process and not be deflected by a hundred new great ideas, so that a few great ideas can take root and flourish. The danger of being so-open-minded that we go along with overwhelming numbers of shiny new ideas, resulting in what’s been called the “Christmas Tree School,” is probably a bigger danger. Here again, there is no escape, as may be deduced from the fact that the term “uncompromising” is either a compliment or an insult, depending on the issue and your perspective.

Being Hopeful and Realistic 

Schools face myriad challenges, and sometimes place impossible demands on Heads who seek to lead diverse communities within which may be found fundamentally different paradigms of education. As visible barometers of school mood and culture, Heads have to avoid any hint of public fatigue, or worse, cynicism. A Head’s role is to supply hope and optimism about the future, especially when those qualities are in short supply, and with a very close realistic eye to the facts, lest the optimism be seen as smoke and mirrors, a result of foolish naiveté. I recall the early days of Covid-19, when in March I named the possibilities of high health risks, of school closure, no graduation, no travel, no socializing. Optimism of the “I’m sure it won’t happen here” type would have been profoundly damaging; but what was helpful was to note that, while as a very open country Singapore was likely to suffer, it was also led by a profoundly competent Government, capable of mobilizing highly effective evidence-led responses. And so optimism in the face of the looming pandemic was justified. 

These four tensions - and others - point to the fact that schools are complex places where there are few singular truths. Heads need to be aware of these paradoxes, and the most successful seem to find one of two ways to address them. 

The first way is to tightrope between the two poles - which is to say, find the “midpoint.” This sounds very reasonable (Aristotle would be pleased), but it’s not straightforward. What, for example, does halfway between resolute and being open-minded mean.... being quite resolute? Being a bit open-minded? There may be times when the midpoint approach works, but there’s also a danger of it being too anodyne and gray, too wary of offending anyone by actually taking a position.

The second (and in my view better) way is to embrace the contradictions; researchers Denison, Hooijberg, and Quinn argue that leaders familiar and comfortable with paradox can “exhibit contrary or opposing behaviors as appropriate or necessary while still retaining some measure of integrity, credibility, and direction.” So tightroping might be an option, but so might adopting either end of the tensions listed above. That seems to me to capture these paradoxes in its own paradox! And while it has the ring of truth, it's also a hard pill to swallow - that the best leaders can be inconsistent and self-contradictory, while genuinely retaining and authentically conveying their own integrity. This is perhaps a simple reflection that the need for multiple perspectives trumpets the need for consistency; for as Walt Whitman put it rather more poetically, “Do I contradict myself? / Very well then I contradict myself, /(I am large, I contain multitudes.)”

All this points to the fundamental and somewhat ineffable quality that I have come to see is at the heart of successful Headship - that of good judgment; which would allow the perfect Head to dance between the various contradictions with grace, authenticity, and perhaps even a bit of joy. It’s not an easy quality to pin down, and of course, there are no perfect Heads. It's too easy to expect perfection and be let down when we all turn out to be human and fallible. In today's rather star-struck celebrity culture we may expect to find someone who will have all the answers - but that's a myth, and perhaps we need to be more realistic. Writer Anaïs Nin put it well, "Those who see giants are still looking at the world through the eyes of a child.”

Read more about The Complexities of Head of School Leadership, Shaping Lives and Building Legacy, and The 200 Percent Dilemma.

References

Alchin, N. (2024) Authenticity:What’s really going on? Education, Schools, Culture.

Baumeister, R. (2019) Stalking the True Self Through the Jungles of Authenticity: Problems, Contradictions, Inconsistencies, Disturbing Findings—and a Possible Way Forward Review of General Psychology Vol 23, Issue 1.

Denison, D. R., R. Hooijberg, R. E. Quinn. (1995). Paradox and performance: Toward a theory of behavioural complexity in managerial leadership. Organ. Sci. 6 (5) 524-540.

Ellis, L (2014). The Paradox of Faith vs. Reality. 

Witman, W. (1855) Song of Myself, 51