Two leaders can have twenty years of experience.
One has developed remarkable insight over those twenty years. The other has simply repeated the same year twenty times.
The difference is important.
Experience is what you have seen. Insight is what you have learned from what you have seen. More importantly, it is what you have learned that enables you to ask better questions. The kind of questions that uncover assumptions, reveal what sits beneath the surface and occasionally lead people towards answers they had not previously considered.
The longer I work in education, the more convinced I become that insight is one of the most undervalued capabilities in leadership, governance and recruitment.
We regularly celebrate expertise. We value qualifications, technical knowledge and years of experience. All of those things matter. Yet some of the most influential people I have encountered in schools possess something different. They have an ability to see patterns that others miss. They connect seemingly unrelated observations. They hear what is being said, but they also pay attention to what is not being said. And they ask a better question.
Insight is difficult to define because it is often mistaken for other things. It is not intelligence, although intelligent people may possess it. It is not expertise, although expertise can contribute to it. Nor is it simply experience. I have met people with decades of experience who continue to bring fresh perspective to every challenge, and others who seem to approach each new situation exactly as they approached the last.
I have come to think of insight as what happens when curiosity meets experience and is given enough time to reflect. It might be difficult to develop in environments that are constantly busy – like schools. It requires constant curiosity. It requires observation. Most importantly, it requires reflection. Sometimes, and perhaps more often than we realise, that reflection does not happen between the confines of 8am and 5pm. It happens on a long run, in the gym, on a drive home or while doing something entirely unrelated to the challenge at hand. And it rarely emerges while somebody is rushing through emails, preparing reports or working through compliance requirements. Those activities are necessary, but they seldom create the space required for deeper reflection.
I suspect naturally curious people have an advantage. They tend to ask more questions. They are interested in understanding rather than simply observing. They seek context rather than conclusions. People can learn frameworks that encourage deeper thinking. Yet there does seem to be an interesting tension. Some people appear naturally drawn towards patterns, relationships and questions in a way that others are not.
One of the questions this raises for me is whether schools are good at recognising insight when they see it.
The reality is that insight can emerge from almost anywhere within a school community. The insightful people in organisations are often not who we expect them to be. They are not always the loudest voices in the room. Sometimes it is the Head of Year who knows exactly how a new initiative will be experienced by students. Sometimes it is the enrolments officer who can sense shifts in parent sentiment six months before enrolment numbers begin to change. Sometimes it is the student services officer who notices patterns in student wellbeing concerns long before they appear in reports. Sometimes it is the IT manager who understands how staff actually work, rather than how leadership thinks they work.
What these people often have in common is not authority. It is perspective. Through the nature of their role, they are exposed to hundreds of small interactions, observations and conversations that others never see. Over time, those observations accumulate. Patterns begin to emerge. And when those patterns are combined with curiosity and reflection, insight develops.
The challenge for leaders is that these people are often easy to overlook. Their insight does not always arrive in a board paper or a formal report. More often it arrives in the form of a question, a quiet observation or a perspective that causes others to pause and reconsider what they think they know.
Perhaps one of the most important questions leaders can ask is whether they know who these people are in their school communities and whether they have created the conditions for their insight to emerge? Perhaps this would be a worthwhile exercise for every leadership team. If you asked each member to identify the most insightful people in the school, I suspect the overlap would be less than expected. I also suspect some of the names would surprise you.
At Hutton Consulting Australia, we often talk about insight as one of the foundations of our work. Not because we believe we have a monopoly on it, but because our team has spent many years deep in the weeds of school leadership. Through our work today, we are fortunate to work alongside schools experiencing growth, schools navigating decline, schools managing succession, schools rebuilding trust and schools preparing for significant change. Over time, those conversations create perspective.
We learn that schools which appear almost identical on paper can require entirely different leadership approaches. We learn that the challenge being discussed is not always the challenge that needs solving. We learn that the first question being asked is often not the most important one.
Often the greatest value we provide is not an answer. It is a better question. A question that reframes the challenge being faced, reveals a blind spot or helps a board, principal or executive team see their situation more clearly.
I think that is what insight really is.
Not having all the answers, but knowing how to ask a deeper question. The question beneath the question.

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