What We’re Actually Asking When We Say “Think More Strategically”

Whenever I hear someone say, “We need to think more strategically,” I find myself wondering what we are actually asking people to do.

I have sat through and led many strategy processes, sometimes building elaborate plans for whole organizations, companies, and even countries. What has always struck me is how often something essential goes unnamed. Strategy processes are decision-making processes. They try to build alignment and coherence in the present while making choices about an uncertain future.

The plans they produce can create a comforting sense of order. Underneath every strategy, though, is a collection of assumptions - about what the future will look like, which events will matter, what will stay possible, and how other people will behave. Those assumptions are not always made explicit.

Here is the short version of where I have landed. Strategic thinking is the discipline of diagnosing the system around a decision, making its assumptions visible, and choosing how to act when the future cannot be known. Everything below is what that looks like in practice.

The assumptions hidden inside a strategic choice

I remember one organizational question we returned to for at least three years running: should we expand through country offices or through regional thematic offices?

The question looked strategic. It was about structure, geographic reach, and long-term growth. Yet it carried assumptions we rarely examined. We assumed the organization would keep expanding. We assumed that opening offices was the way to expand. We assumed the line between country offices and regional thematic offices would turn out to be the decisive one.

Even then, I kept wondering how we were supposed to make the decision. What were the criteria? What would have to be true for either option to be the right one?

In the end we did neither. Funding contracted, and instead of opening new offices we had to close the country offices we already had.

This did not mean the strategy process had failed. It exposed a weakness in the question we had been asking. We were comparing two versions of a future we already expected, and giving almost no thought to the futures in which our central assumption, continued expansion, did not hold.

Being correct is not the same as being strategic

Strategic thinking shows up well beyond big organizational decisions. Sometimes it is clearest in small, human situations.

Recently my mother’s lawyer in the south of France found a legal error in a document signed forty-five years ago. Once she saw it, she became convinced it had to be corrected to head off future problems.

Factually, she was right. There was an error.

Strategically, her plan was questionable. The harder she pressed the point that the document was defective, the more she raised the chance that someone would contest a document that had gone unchallenged for forty-five years. There was also no realistic way to get everyone to sign again. Some of the original parties had died, and the interests of those still living had shifted.

Her analysis fixed on the defect in front of her. It did not account for the wider human system that correcting it would set in motion.

That distinction matters. Being right is only the start. Strategic thinking is about understanding what your actions set in motion. A person can be factually correct and strategically unwise, naming a real problem while proposing an intervention that makes things worse. Good strategic judgment looks past the immediate issue to the incentives, relationships, timing, second-order effects, and the likely responses of other people.

Strategic thinking is a diagnostic practice

So what do we mean by thinking more strategically?

Each of those situations points the same way. Strategic thinking is a set of diagnostic skills that can be learned and practiced. It is the work of surfacing the assumptions buried in a question, reading the wider system you are about to act on, and anticipating how people will respond, and then deciding your move. It is what the country-offices question was missing, and what the lawyer’s analysis left out. The practice runs as a loop: you observe, diagnose, decide, and observe again.

It asks:

• What is really going on beneath the visible issue, and what assumptions are built into how we framed it?
• What wider system, incentives, and relationships will shape how people respond?
• What lies outside our control, and which futures do we need to stay ready for?
• What would have to be true for this choice to work?
• What might our intervention set in motion that we did not intend, and which parts of it can we reverse if we are wrong?
• What signals would tell us to hold course, adapt, or stop?

When the uncertainty runs so deep that no diagnosis resolves it, you still have to act - a challenging case I take up in Lead Anyway.

Tools improve judgment without removing uncertainty

Decision-making tools are part of a strategic mindset. They help teams surface assumptions, compare options, trace consequences, and tell short-term actions apart from long-term commitments.

An options-and-consequences decision tree forces you to examine what you hope a decision will achieve and what might follow from it. Scenario planning takes two uncertainties you cannot control - say, whether funding expands or contracts, and whether the politics allow cooperation or turn to fragmentation - and crosses them into four plausible futures, so you can ask what you would do in each and what early signs would show which one is arriving. A pre-mortem has a team imagine why a decision failed, before they commit to it. Signals and thresholds name in advance when to stay the course and when to pivot. And a discipline I call the FOG Filter - frame the situation, orient to what matters now, gauge how the system responds - helps you move when you have to act before the picture is clear.

The value of these tools is in the quality of conversation they force, and in making the reasoning visible. They let people challenge assumptions, compare interpretations, and understand why a particular choice is being made. Every strategy is still part analysis, part guess, and part bet.

Strategic thinkers know this. They treat a strategy as a working proposition. It holds as long as its assumptions hold, and they revise it when those change. They make a contained move, treat it as a hypothesis, watch what it teaches them, and adjust. They hold the plan lightly and the purpose firmly.

Strategy as an iterative leadership practice

To think more strategically is to diagnose before you decide, and to keep testing your read as the situation moves.

It means seeing the challenge in front of you while noticing the system around it, and remembering that people will respond to your interventions out of their own interests and histories.

Strategic thinking is the discipline of making better bets about an uncertain future while creating enough coherence for people to act in the present.