Leadership Paradoxes

[Adapted from a recent article in The International Educator]

Jeff Paulson, CEO of the Academy for International School Heads, asked me to respond to three prompts: What do you want people to know about the Head of School Role? What are the challenges?What have you learned that you would like others to know?

I was initially pretty skeptical about writing on this topic. There are a million Heads’ leadership blogs (including mine) and LinkedIn posts about this sort of thing, and besides, answering these three prompts requires something 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; more intimate even.

It feels slightly self-indulgent to write from a personal, rather than professional perspective (does anyone even care?). And it’s rather exposing, being positive seems aggrandising; being negative feels like self-pitying. 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 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 that they 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 it is very challenging). The good news is that – perhaps more than for other tensions listed below – 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 blogging? – and other public appearances. These Heads might say they need to remain strategic or that they leave the details to others or are externally focussed. I have seen this, and it is, in my view, a profoundly mistaken approach. The Head needs to know the institution very well indeed, while always being able to rise above the details.

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. These situation can be very ugly, and must be avoided. At the same time, 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; and while every leader needs to take care of individuals, the role of leadership is also fundamentally about the institutional perspective.

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. 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 

Heads lead diverse communities within which may be found fundamentally different paradigms of education. As visible barometers of school mood and culture, they 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 and 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, lockdown, no graduation, no travel, no socializing and so on. 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.

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These four tensions point to the fact that schools are complex places where there are few singular truths (I don’t know the extent applies to other organisations, but I imagine the fact that our children are involved in our endeavours makes a significant difference). 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 some 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 grey, 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 hardly offers much guidance! It’s also a hard pill to swallow – can the best leaders really be inconsistent and self-contradictory, while genuinely retaining and authentically conveying their own integrity?

Perhaps this is just a reflection that in a complex situation with diverse stakeholders, the healthy need for multiple and competing perspectives is more important than the need for consistency. Or as Walt Whitman put it rather more poetically:

All this points to the fundamental and somewhat ineffable quality that I have come to see is at the heart of good leadership (in any sector, not just education) – that of good judgment; which would allow the perfect 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, no-one is perfect. As it’s impossible to simultaneously achieve all the elements of tension I have mentioned (and no doubt plenty of others too) there will always be gaps to point to. 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.

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. 
• Whitman, W. (1855) Song of Myself, 51