We live and lead in a world that resists prediction. Markets shift. Teams fracture. Strategies are disrupted by unexpected events that, in hindsight, seem obvious. So why do smart, experienced leaders still get caught off guard?

The Problem Isn’t the Information

New research from Stanford GSB[1] offers insight into this question — and the answer has less to do with the quality of our information than with how we’re processing it.

Researchers studied what they call “strategic surprises” and found that our thinking style creates predictable blind spots. When we think too abstractly — engrossed with the “why” behind an issue — we rely on broad mental models and historical patterns. This can cause us to misjudge threats, overlook nuance, or assume others will behave in predictable, stereotypical ways. When we think too concretely about challenges — fixated on the “how” — we get absorbed in the immediate details. We can miss the larger patterns unfolding around us.

Neither approach, on its own, is sufficient.

Recognizing the Signal

I have observed similar outcomes in organizations. Leaders who work primarily above the tree line — always in “why” mode — often miss the friction accumulating at ground level. Those who operate in the weeds — heads-down in execution, always in “how” mode — are often the last to sense a cultural or strategic shift coming. Both are capable. Both are informed. And yet both can be genuinely surprised as unexpected events arise.

Here’s an example that isn’t that unusual. A senior leader notices one of her direct reports has gone quiet in meetings — shorter answers, less engagement. She checks in directly. He says everything’s fine. She moves on. Six months later, she learns the entire team has been quietly frustrated for over a year about unclear decision-making authority. The silence wasn’t personal. It was a signal she missed, because she was looking at the individual, not the system.

A Different Kind of Readiness

What the Stanford researchers propose is simple, but not necessarily easy: toggle between the “why” and the “how.” It requires intention to deliberately shift from the abstract to the concrete and back again. You might ask not just why a competitor might move in a certain direction, but what they’ll likely do tomorrow — and what they’ll likely do next year. Consider not just why a team dynamic feels strained, but where the points of tension exist. What specific interactions are producing that strain?

I think of this discipline as systemic intelligence — the ability to hold both the pattern and the particulars simultaneously. Systemic intelligence recognizes that what shows up as an interpersonal conflict, a communication breakdown, or resistance to change is rarely just that. It’s often a signal of something larger.

Take the VP who rolls out a reorganization his leadership team has been planning for months. The announcement lands with a thud. He’s baffled. The strategy was thoroughly vetted. It was sound. However, he missed that two teams have a long-standing, unspoken rivalry that the new structure just amplified. The “why” was solid. Anticipating “how” it would land required a different perspective entirely.

Leaders who navigate uncertainty most effectively aren’t necessarily those with the most information. They’re the ones who can shift their lens — strategically and fluidly — between the forest and the trees.

The human brain is constantly trying to predict what lies ahead. The question isn’t whether we’ll form expectations. We will. The question is whether we’re consciously and intentionally assessing those expectations from more than one vantage point.

That’s not a one-time exercise. It’s an ongoing practice.

What’s one situation you’re dealing with right now where a shift in thinking — from the forest to the trees, or vice versa — might reveal something you’re missing?

What does this outcome tell me about the other options I haven’t tried?