I spend a lot of time talking with school leaders about strategy. Still, I increasingly find myself wondering whether we focus too much on strategy and not enough on becoming better strategists.

They are not the same thing.

A leader can facilitate a strategic planning day, understand the school's strategic plan and confidently report against its priorities without necessarily having developed what I would call strategic dexterity: the ability to notice change, interpret what it might mean, challenge an established way of thinking, make difficult choices and adapt when the evidence changes.

The contrast is more than semantics because strategic dexterity isn't something leaders can improve marginally. Like financial literacy, negotiation or interpersonal skill, it is an aptitude that needs to be honed continually.

The difference is that strategic dexterity helps a leader decide when and how to deploy those other capabilities.

Is strategic dexterity really that important?

School leaders already face an intimidating list of capabilities they are expected to master. They need to understand teaching and learning, develop people, build relationships, manage finances, negotiate, communicate, govern risk and manage increasingly complex organisations.

So why elevate strategic dexterity?

I don't think the evidence supports the claim that it is more important than everything else. In fact, the Australian Professional Standard for Principals deliberately presents leadership as an integrated model. Operational, relational, strategic and systemic leadership all matter.

UNESCO's recent Global Education Monitoring Report similarly identifies setting expectations, focusing on learning, fostering collaboration and developing people as essential dimensions of educational leadership.

Relationships certainly shouldn't be relegated.

A 2025 meta-analysis of 68 studies (Hallinger, Liu, and Chen 2025) found a particularly strong relationship between principals' instructional leadership and teacher trust.

Perhaps, then, strategic dexterity sits in a slightly different category.

Financial literacy can tell me what my school can afford, but not necessarily what deserves the investment. Relational capability can help me bring people together, but it cannot determine where we should be heading. And, likewise, negotiation can reconcile competing interests, but it cannot tell me which interests should ultimately prevail.

Strategic dexterity helps integrate these capabilities.

Research into what are known as dynamic managerial capabilities (DMCs) supports this broader idea. A recent synthesis (Baishya et al 2025) identified managerial cognition, issue interpretation, cognitive biases, human capability, and networks as foundations that enable leaders to effect strategic change in dynamic environments.

The question, therefore, is how we train it.

First, create the space to see

Telling a principal to "make more time for strategy" is almost insulting.

The 2025 Australian Principal Occupational Health, Safety and Wellbeing Survey reported that school leaders were still working an average of 53.9 hours during term, with sheer quantity of work their greatest source of stress.

So, I wouldn't ask a leader to find another hour. And I certainly wouldn't suggest taking it from family, exercise or recovery.

I would ask them to exchange an hour.

Take a moment to look at last week's calendar and see if there's an hour you spent on something someone else could have reasonably handled. Maybe a meeting you didn't really need to join, an operational approval that could be delegated, or a recurring discussion that could be shortened to 30 minutes instead of an hour. By making these small adjustments, you can free up time for more important priorities and create a more balanced schedule.

Then protect that hour for strategic thinking.

There is some science behind doing this. A 2026 Strategy Science experiment (Kanis, Mann, and Stumpf-Wollersheim 2026) found that time pressure narrowed the breadth of the mental representations people constructed when considering strategic problems. Under pressure, we tend to stay closer to familiar categories rather than search more widely.

I would give that hour a simple structure. Record three things that appear to be changing, two possible implications for the school and one assumption those changes might challenge.

Importantly, don't only scan education. Look at demographics, employment, technology, housing, consumer behaviour, regulation and social trends. Research into environmental scanning (Harris and Brooker 2025) describes the importance of looking for weak signals: small developments that may be easily overlooked today but become strategically significant tomorrow.

Don't turn every signal into an initiative. Keep a one-page strategic intelligence log. After four or five weeks, look across it.

What keeps appearing?

If I were measuring progress, I wouldn't count how many trends I had identified. I would ask whether important issues were starting to appear on my radar before they became urgent problems.

Practise seeing the problem differently

School leaders become very good problem-solvers. Experience helps us recognise a situation quickly and retrieve a response that has worked before.

Strategically, that can also be a weakness.

Research examining higher-performing strategic decision-making teams (Cohen and May 2025) found that broad framing and making strategic rationale explicit were among the practices associated with better decisions. Furthermore, cognitive flexibility was positively associated with the quality, understanding and commitment surrounding strategic decisions.

So, I would introduce a discipline: no important strategic problem gets to keep its first definition.

"Our enrolments are declining" might initially become "our marketing isn't generating enough enquiries".

But another frame might be "our value proposition doesn't sufficiently convince families".

A more uncomfortable one could be "the market our current school model was designed to serve is changing".

Similar identification of the symptom, but three very different strategic responses.

For each significant problem, I would write the obvious explanation, a systemic explanation and an uncomfortable explanation. Then ask what evidence would distinguish between them.

There is another useful way to train this muscle: expose the problem to someone outside the echo chamber.

Once a month, give one strategic question to someone who doesn't share your professional context. It could be a recent graduate, business leader, parent, technologist or someone working in an entirely different industry. Ask them: What strikes you about this that you think we're not seeing?

The test isn't whether they solve the problem. Rather, it’s whether they cause you to alter an assumption.

If nobody outside my normal circle has challenged one of my assumptions over the past few months, I would start wondering about the depth of my network.

Make the thinking behind choices visible

Schools make decisions constantly, but far fewer decisions constitute genuine strategic choices.

The difference, for me, is trade-off.

For every consequential decision, I would document or diarise my response to the following: What are we choosing? What credible alternative are we rejecting? What are we giving up? Which assumption makes this sensible? What evidence would cause us to reconsider?

Strategy isn't demonstrated by stubbornly sticking with a decision. Dexterity includes retaining the capacity to move when the underlying conditions change.

Research on strategic decision-making teams found that stronger teams were more likely to make their strategic rationale explicit and to be cautious about unnecessarily restricting future flexibility.

I would also deliberately build opposition into significant choices. Ask somebody to construct the strongest argument against the preferred direction.

AI can be particularly useful here, although perhaps not in the way we sometimes imagine. I wouldn't ask it to determine the strategy. I'd ask it to identify assumptions, offer alternative explanations, expose second-order consequences or argue vigorously against my preferred option.

Interestingly, the 2026 Strategy Science experiment found LLM use broadened participants' mental representations but did not significantly improve strategic foresight. It also increased information overload and reduced psychological ownership.

For now, that suggests to me that AI may be more valuable as a sparring partner for human thinking than as the strategist.

Finally, keep score

This may be the most important practice of all.

I don't think we can master something we never review.

For major strategic judgments, I would keep a simple decision journal. Record what I expect to happen, why I believe it will happen, what I am least certain about and which early indicators should tell me whether my assumptions are holding.

Then put a date beside it and return to it later.

Six months on, ask whether the original reasoning was sound given what was known at the time.

Were my assumptions accurate? What did I miss? Did I notice contradictory evidence early enough? Did I change course when I should have?

That is how strategic experience becomes strategic learning.

Mastery requires repetitions

I’ve written previously about the need for school leaders to develop their strategic muscle, but increasingly I think that requires something more deliberate than simply participating in strategy more often.

It requires repetitions.

Continuously scanning the environment, reframing problems, and exposing assumptions. Then challenge the choices you made. Invite disagreement and predict outcomes. And before you put it through the rinse-and-repeat cycle, review your judgments.

And this leads me to a slightly uncomfortable epiphany.

Twenty years of school leadership does not automatically equal twenty years of strategic practice.

A leader can become extraordinarily accomplished at managing the institution in front of them without substantially improving their ability to anticipate the institution that may be needed next.

For leaders who want to become great strategists, strategic dexterity cannot remain something exercised occasionally when the strategic plan is due for renewal.

It needs to become part of how they lead every week, because mastery isn't demonstrated by always getting the future right.

It is demonstrated by becoming progressively better at seeing sooner, thinking more broadly, choosing more deliberately, and adapting faster when the world refuses to behave as expected.