Curiosity as A Strategic Stance

Strategy isn't a periodic event—it's continuous, evolving work. Yet too often, organizations equate strategy with strategic planning, as a discrete exercise with clear start and end dates. 

When heads, leadership teams, and board members actively resist this limiting view and instead embrace curiosity as an ongoing strategic stance, they unlock significantly more potential for their schools. In this article, I’d love to explore why. 

The plan is not the strategy.

It can help to unpack the commonly used misnomer of “strategic planning,” which encourages us to conflate two related, but different, things: your point of view on the future and the actions you take as a result. (I’m indebted for this insight to Roger Martin of the Rotman School of Management.)

In other words, your to-do list should be rooted in your strategy – but it is not the strategy itself. Strategy is an ongoing commitment, a way of learning more about the world and making decisions based on that learning. 

Every five years or so, a strategic planning cycle might mean pulling your constituents together more formally, engaging in a particularly intensive cycle of meaning-making, or making the work of strategy more explicit.

But the work of building a shared point of view about the future never really ends: you never have all the information, and the world never stays still. Strategy, rooted in curiosity, is work that happens before, during, and after a formal strategic planning cycle.

Prepare for a strategic planning cycle by engaging in strategic, generative thinking.

With one client’s board, we took a year to engage in sustained curiosity about the future before beginning a strategic plan. This went farther than exploring the future of the school: we also explored what might be coming socially, technologically, economically, environmentally, politically, and legally.

That sustained futurist thinking helped their board shift out of a near-term focus on the COVID pandemic and re-orient themselves to the long-term, strategic work that’s the primary work of any board. By getting curious about what might be emerging in the world, it also helped them frame a shared set of key strategic questions before entering into the following year’s strategic plan.  (Our “Futureproofing Your Board” service is one way to do this at your school.).

Generative thinking isn’t only for boards – it’s also a habit worth building among leadership teams and frontline staff as well.  By engaging in this work consistently, you can help your community build habits of curiosity about what’s happening, loosen attachments to their individual concerns, and build a shared mental map of the questions facing the school. 

When beginning a strategic planning cycle, approach the work as a designer – giving yourself as much time for questions as for answers.

A truly strategic process begins by getting more curious about what is happening in your communities and the range of potential pathways forward.

A traditional strategic process often frames data as a pathway to certainty, and indeed, data is a critical tool for decision-making. Nevertheless, when starting a strategic plan, it’s often more productive to see data as a pathway to questions.

When you review that parent survey, admissions statistics, or – as we like to do at L+D – in-depth, 1:1 interviews with community members, take time to identify the questions that emerge. 

• What is unsettled or uncertain? 

• What is surprising or contradictory? 

• What is changing – for our community, and for our context?

• What can you learn about what motivates the people in our community – students, families, employees, and others?

Often, that impulse will guide you to the places where the committee should spend more time. By taking the time to identify better questions, you make it more likely you will find your way to useful answers.

This kind of discovery work can be challenging because it is disconfirming. A long-treasured tradition may turn out to exclude the full range of your community; a lauded academic program may reveal itself to be very 1998. 

It can also be challenging because, if you pair this with the futurist thinking I describe in the section above, it can heighten your collective sense of uncertainty. When you design for the present day, you can take comfort in your expertise. But when you design for the world of 2035, you have to begin again as learners.

This discomfort is an important element of making collective strategy. By loosening our individual attachment to our individual mental models, a shared process of inquiry can then help a community build a shared point of view – both about the future and about what the school should be in that future. 

After the board has approved a strategic plan, stay agile with a mindset of iterative implementation.

For many in your community, it may seem like strategy is over when you publish your board-approved plan: now, the logic goes, you can focus on implementation. This framing may also come from a simplistic understanding of hierarchy, one where leaders own the decision-making and the staff are simply doing. 

But strategy is a compass, not a map. Ideally, the school isn’t taking its eyes off the road to trace the lines in the metaphorical atlas. As conditions change, the school should, too. 

Here’s an example: years ago, a client had an unexpected opportunity to acquire an adjacent piece of property, only months after the board had approved the strategic plan. In other words, strategic planning was over, but strategic questions weren’t. 

In the end, the school evaluated the acquisition in terms of whether it would help them occupy the unique space in the market the strategy called for them to claim. This new opportunity could be weighed in terms of how well it helped them differentiate themselves. Strategic questioning and strategic decision-making continued. 

During implementation, the interplay between strategic questions and strategic decisions continues on smaller levels as well. Given a commitment to build a new innovation center, what programs will best promote the mindsets your strategy calls for? Given a commitment to end AP courses, what advanced offerings will best advance your strategic vision? Like a series of nested dolls, every implementation step is an opportunity to ask strategic questions, getting finer and finer as you go. 

Framing implementation as ongoing strategic work is an opportunity to generate buy-in and give appropriate authority to the people closest to the situation. A head, a leadership team, and frontline faculty and staff should all be engaged in strategic thinking, just at different levels of resolution.

As a practical matter, you could provide a structure for this reality by running implementation planning as a series of annual cycles. While keeping your eye on the goals you’ve set for yourselves, a team – whether the board, a senior leadership team, or a faculty committee – can look back over the last year, not only with a checklist but with a stance of curiosity. 

• What progress have you made, and what went differently than you expected? Why might that be?

• What’s changed since you last checked in? What questions does it raise, and what decisions might you make differently?

• What have you learned last year, and what will you need to do to act on that learning?

After asking those kinds of questions, you can plan the next 12 months with a shared understanding that is much more likely to be true. Doing so challenges the commonly held binary of strategy and implementation, offering opportunities for many stakeholders to flesh out strategy through the implementation of new initiatives. 

In the end, strategy isn't a document gathering dust on a shelf—it's a living practice of institutional curiosity. By embracing uncertainty rather than fighting it, leaders transform strategy from a periodic ritual into an organizational mindset. 

When curiosity becomes your strategic stance, planning never truly ends—it evolves, breathes, and grows alongside your organization, ensuring that your compass remains calibrated even as the landscape shifts beneath your feet.

(You can request a copy of our strategic white paper, or read the article I co-wrote with my colleague Crystal Land, if you’re curious to learn more about what this might look like in practice.)