The Expert Intuition Trap

The Central Error of Modern Leadership

Featuring an interview with William Duggan, Senior Lecturer at Columbia Business School and author of Napoleon's Glance, Strategic Intuition, and The Seventh Sense

Last week delivered the kind of clarity that only arrives when several things go wrong at once, in public, at the highest levels, simultaneously.

On Wednesday night, President Trump addressed the nation on a war entering its second month and declared that core strategic objectives were “nearing completion”, a formulation that raises the question of how you complete objectives you never articulated, in a war you never defined, against an enemy that has not agreed to lose.

A month in, with no stated endgame, oil markets in convulsion, and the Strait of Hormuz closed like a fist, the president offered the country what he has always offered: the performance of certainty in the total absence of its architecture. Meanwhile, The Economistreported from Beijing that Chinese elites see no grand strategy behind any of it — not Iran, not Venezuela, not the tariffs — just transactional improvisation by a leader they study the way sailors study weather: dangerous, unavoidable, and fundamentally ungovernable.

On Wednesday morning, Nike hit an 11-year stock low — shares down 45% since Elliott Hill took over as CEO — after Hill convened an all-hands meeting and offered his employees less a novel vision than a confession: “I'm so tired, and I know you are too, of talking about fixing this business.” Three Wall Street banks downgraded the stock before lunch. Hill has been in the job since October 2024. He inherited a strategy vacuum and has filled it with effort, sincerity, and the kind of operational focus that looks like leadership until the stock price tells you it isn't. “I want to move to inspiring and driving growth and having fun,” he told his employees, a sentence that contains its own diagnosis, because a leader who has to announce that he'd like to start having fun has already told you everything about the conditions under which he's been operating.

And five days earlier, Takeshi Sano had addressed Dentsu's global workforce for the first time as CEO. Dentsu is the world's fourth-largest advertising holding company, the Japanese counterpart to WPP, Omnicom, and Publicis; Sano was stepping into the role after a $2.18 billion write down, a failed attempt to sell the international business, and organic revenue declines across every region outside Japan. His message was execution, client-centricity, cross-capability collaboration. His description of the company's future could have been delivered by the CEO of any holding company on earth. It was a competent address that answered every question except the one that matters: execution of what? Dentsu had just posted the largest loss in its history not because it lacked the ability to execute, but because no individual mind inside it had produced a strategic narrative worth executing against, and no organizational process, however disciplined, can substitute for that.

Three different arenas. Three sets of leaders making consequential decisions at the point of maximum complexity, where all the forces bearing down on a system converge simultaneously and the old maps go blank. And an entire global commentariat of pundits, analysts and journalists confidently interpreting those decisions as evidence of strategic thinking or its absence. Every one of those interpretations is built on the same unexamined assumption: that we can tell, from the outside, whether a leader is operating on genuine strategic insight or something else entirely.

William Duggan says we can’t. And he has spent two decades at Columbia Business School explaining why.

The Art of the Recombination

Duggan is the author of Napoleon’s Glance, Strategic Intuition, and The Seventh Sense, a body of work that mapsthe cognitive mechanism behind strategic breakthroughs, from Napoleon’s battlefield victories to the founding of Google.

In 2007, Strategy+Business named Strategic Intuition the best strategy book of the year. He’s taught the subject to MBA students, executive education cohorts, and thousands of corporate leaders around the world. His foundational claim is that neuroscience has understood how strategic thinking actually works since the 1990s, and that virtually every field that depends on it — business strategy, military planning, political decision-making, the entire apparatus of leadership development — has failed to update.

I reached out to Duggan because I thought his framework might be the sharpest available tool for making sense of the current moment. He initially declined, not out of sensitivity, but on methodological grounds that turned out to be more interesting than the interview I’d originally proposed. He can’t assess anyone’s strategic thinking, he said, without deep access to their internal cognitive record. Public statements are PR. Presidential addresses are PR. CEO earnings calls are PR. None of it constitutes evidence of what a leader was actually thinking.

What he could do was explain how the mechanism works. The preconditions. The failure modes. The difference between what looks like strategic insight and what actually is. And then let readers apply the framework to whatever they're watching.

What follows is the result of that conversation.

The starting point is a revolution that most decision-makers missed. “Improved brain scan technology led to a revolution in neuroscience in the 1990s,” Duggan told me, “that various decision sciences have failed to take into account. They remain anchored in outdated notions of how the human brain works.”

The updated model is simpler than you’d expect, and more consequential. The brain operates on learning and memory. Learning puts elements on the shelves of your mind. Memory recombines them as thoughts to suit the situations you encounter. That’s it. That’s the mechanism behind every strategic decision anyone has ever made.

But the recombination happens in two fundamentally different ways. And confusing them is, in Duggan’s framework, the central error of modern leadership.

Two Kinds of Intuition

The first kind Duggan calls expert intuition.

You encounter a situation that’s similar to one you’ve faced before, and your brain repeats a previous thought in its entirety. This happens so fast that people call it “instinct.” It feels automatic because, cognitively, it is — your brain has already solved this problem and is running the same solution again. For a nurse in an emergency room, a firefighter entering a burning building, or a trader reading a familiar market pattern, expert intuition is essential. Speed is everything, and the situation is genuinely familiar.

The second kind Duggan calls strategic intuition.

The situation is new. Genuinely new, not superficially new. And your brain needs to search more widely across its stored experience, pulling elements from different domains, different time periods, different contexts, and combining them in a configuration you've never assembled before. That recombination arrives as a flash of insight. The military calls it coup d'oeil, a stroke of the eye, Napoleon's glance. In Duggan's research, it is the cognitive event behind every genuine strategic breakthrough in history.

Here is the critical distinction: expert intuition feels exactly like strategic intuition.

Both arrive as a flash. Both feel like insight. Both produce confidence. But one is a repetition of the past and the other is a creative recombination for the future. And the leader experiencing them often cannot tell the difference in the moment. “The biggest obstacle to strategic intuition is expert intuition,” Duggan told me. “You think a situation is similar to one you encountered before and rely on expert intuition, but in reality there are enough new elements that you need to slow down and let your brain search your memory more widely for elements to combine.”

This is the expert intuition trap. And if there is a defining leadership failure mode for 2026, this is it. Not incompetence, not cowardice, not corruption, but the wrong kind of pattern recognition applied at the wrong level of complexity by people who feel more certain than they have any right to feel. Hunter Thompson, writing in a different era of American vertigo, put it in terms that have aged into prophecy: “We are living in dangerously weird times now. Smart people just shrug and admit they're dazed and confused. The only ones left with any confidence at all are the New Dumb.”

Duggan's framework gives Thompson's observation a cognitive architecture: the New Dumb are not stupid. They are operating on expert intuition — pattern-matching the present to a past that no longer applies — and the confidence they project is not a performance. They believe it. The mechanism is doing exactly what it evolved to do. It is just doing it in the wrong conditions.

How Patton Worked

If the trap is mistaking a new situation for a familiar one, the escape is a specific discipline: knowing where your thoughts come from.

Most leaders cannot do this. Not because they lack intelligence, but because they have spent entire careers inside a single bounded market, absorbing the same precedents as every competitor, reading the same analysts, attending the same conferences, running the same playbooks. The shelves of their memory are stocked with the same inventory as everyone else's. And when the situation changes, they reach for the same wrong answer at the same time, with the same confidence, and call it strategy. (This is the problem Hardcore Zen was designed to address.)

Duggan pointed me to General George Patton, the best battlefield general on the Allied side in World War II, who addressed this directly in his memoirs. Patton wrote that he was often accused of making snap judgments. But they were actually based on years of thought and study. After such a “snap judgment,” if you asked him where it came from, he could cite quite clearly the precedents he studied that fit the current situation.

This is not instinct. This is the opposite of instinct.

It’s a discipline of deep, deliberate study that becomes so internalized it mimics instinct, producing rapid, confident decisions that look impulsive from the outside but are grounded in a vast library of precedent. Duggan describes Patton as a rare case of someone studying past examples so thoroughly that they become a form of personal experience, resulting in a combination of expert and strategic intuition.

Warren Buffett, Duggan noted, uses the same method — intense study of examples — with similar results. What looks from the outside like an uncanny feel for markets is, from the inside, a disciplined recombination of deeply studied precedent applied to new situations.

The implication is uncomfortable: you cannot tell, by watching someone make a rapid, confident decision, whether they are operating like Patton or operating on autopilot. Both look the same. The difference is entirely internal, and it turns on whether the leader can, if pressed, identify the specific precedents that produced the decision.

When the Glance Stops Working

Napoleon is Duggan’s foundational case. He’s also a leader who had the glance, used it to extraordinary effect, and then lost.

I asked Duggan what his framework says about the failure mode. His answer was precise and, I think, important: “Strategic intuition does not guarantee success. It simply gives you an idea with the best chance of success in the circumstances you face.”

Napoleon, as Duggan notes, won 55 out of 60 battles. His worst loss was the Russian campaign, a failure of strategic intuition through overconfidence. His other famous loss was Waterloo, and that was a close call where he did nothing wrong and almost won. The critical point: “A person does not ‘have’ strategic intuition the way someone has 20/20 eyesight or a good musical ear. The same person can have a good idea through strategic intuition that succeeds, and then a good idea through strategic intuition that fails, and then a bad idea that fails, and even a bad idea that succeeds.”

For the last category — a bad idea that succeeds — Duggan offered Columbus.

By the late fifteenth century, scientists knew the circumference of the earth and accurately calculated that the “isles of the Indies” were more than twenty weeks away by ship, while a ship could only hold nine weeks of supplies. Columbus somehow convinced the Spanish crown to back him anyway. In the ninth week, with his sailors ready to rebel, he hit land. To his dying day he refused to admit that what he’d found was not the destination he’d set out to reach.

Strategic intuition, in other words, is not a character trait. It is not a permanent capacity. It is a cognitive event that depends on conditions, and those conditions can be present one day and absent the next in the same leader.

Presence of Mind and Its Enemies

I asked Duggan about those conditions, specifically about “presence of mind,” which his research identifies as a necessary precondition for strategic intuition to fire. His answer was disarmingly practical.

“I often ask: When you get your best ideas, where are you? Almost everyone replies that it’s when their mind is relaxed in some way — walking, falling asleep, driving, or most famously, in the shower.” Presence of mind, in Duggan’s framework, is the state in which your brain isfree to wander across its stored memory, searching for new combinations that fit a situation you care about. It’s not meditation. It’s not mindfulness in the popular sense. It’s a cognitive openness that allows the recombination process to operate.

And there are exactly three things that shut it down.

Too much focus. Your mind never wanders because you're locked onto a single frame, a single problem definition, a single way of seeing the situation. The shelves of memory that contain the novel elements you need are never visited because your attention never drifts toward them. This is, incidentally, the strongest case for the humanities ever made by a neuroscientist who isn't one — because the shelves that Duggan's framework describes are only as rich as what you've put on them. A leader who has read only strategy decks and earnings calls has a memory stocked with strategy decks and earnings calls. The novel combination that constitutes genuine strategic intuition cannot emerge from a library that contains only one genre. Patton read military history obsessively, yes, but also classical literature, philosophy, poetry. Buffett reads annual reports, but also biography, economic history, and anything that tells him how people have behaved under conditions he hasn't yet encountered. The search can only find what the shelves hold. And the shelves are stocked by what you were curious about before you needed the answer.

Distraction. Your attention is fragmented, not focused, and the sustained cognitive wandering that produces insight never gets the uninterrupted time it requires. This has always been true. What's new is that we've built an entire information architecture designed to prevent the very cognitive state that strategic intuition depends on. The phone in your pocket is an expert intuition machine: it delivers the familiar, the algorithmic, the already-known, at a pace that forecloses the slow, open search through which genuine strategic recombination occurs. And now generative AI promises to do your thinking for you, which means it will do your pattern-matching for you, brilliantly, at superhuman speed, drawing on the largest library of precedent ever assembled. But pattern-matching is expert intuition. It is the recombination of what has already been thought. AI can search the shelves faster than any human mind. What it cannot do is stock them with the lived, cross-domain, emotionally textured experience from which genuinely new combinations emerge. A leader who outsources the search to AI gets back the average of everything that's been tried before, assembled with breathtaking fluency, and mistakes it for insight. The tool is extraordinary. The danger is that it makes the expert intuition trap feel like strategic intuition, at scale, with footnotes.

Negative emotions of all kinds. When you are, as Duggan put it, “literally too upset to think.” Fear, anger, anxiety, defensiveness — any of these can lock the brain into a reactive mode that forecloses the open search strategic intuition requires. Recall what Nike’s Hill told his own employees this week: I'm so tired. That is not a complaint. It is a clinical description of a mind in which the conditions for strategic intuition have collapsed. A leader who is exhausted by the narrative of his own turnaround is a leader whose cognitive resources have been consumed by the effort of sustaining a story that isn't working.

Three obstacles. Read them again. And then consider the operating environment of virtually every consequential leader in the world right now.

The Humility Problem

Perhaps the most consequential thing Duggan said had to do with complexity, the condition of facing a situation so new, so weird and so multidimensional that no single person’s stored experience can contain all the elements needed to address it. I asked what happens when a leader is operating in a domain where they lack the depth of precedent that strategic intuition draws on.

“This question reveals the trap of expert intuition,” he said. “You cannot possibly have in your current memory all the elements that fit a new complex situation. You have to have the humility to say, ‘I don’t know the answer, but I can find out.’ And the method is: search.”

Search. Not instinct. Not decisiveness. Not gut feel. Search — the deliberate, systematic pursuit of examples beyond your own experience that might contain elements relevant to the problem you face.

Duggan pointed to Colin Powell as Secretary of State, facing North Korea, a closed society with opaque decision-making. Powell sent his staff to collect and analyze every past agreement and treaty the regime had made since its founding in the 1950s. That gave him the best possible basis for the next round of negotiations. Not certainty. Not a guarantee. The best possible basis, assembled through disciplined search, not personal intuition.

The implication for anyone watching the current landscape of leadership decisions — in geopolitics, in corporate turnarounds, in institutional strategy of any kind — is straightforward. The leaders most likely to be caught in the expert intuition trap are the ones most confident that they already know the answer. The ones most likely to produce genuine strategic intuition are the ones willing to admit they don’t know, and to search.

What the Pundits Are Actually Doing

I asked Duggan about the media environment, the thing that constitutes the background noise of modern existence — the fact that literally everyone, from the intelligence services in Beijing to the cable news panelist killing time between commercial breaks to the bond trader pricing sovereign risk at three in the morning, is engaged in the same activity: watching leaders move and claiming to know what the movement means.

His answer reframed the entire activity.

In competitive environments, he said, you have to try to put yourself in the shoes of your adversary or other important players, to predict their next moves, “usually in the absence of strong evidence of what they are thinking.” It’s to do what Powell did: find whatever evidence you can, as systematically as you can, and build your best assessment from that, while acknowledging the limits of what you know.

What the analyst class is mostly doing, in Duggan's framework, is something different. They're applying expert intuition to a situation that requires strategic intuition. They're pattern-matching the current moment to historical templates — this is Vietnam, this is Iraq, this is the Nike playbook, this is the turnaround that worked at Apple — and producing confident assessments based on analogies that may not fit. But here is the subtlety: the analogy is not wrong. It's partial. Vietnam explains some of what's happening in Iran. It doesn't explain the rest. Strategic intuition would take the elements that fit from Vietnam, combine them with elements from other precedents that address the parts Vietnam doesn't cover, and produce a new combination. Expert intuition stops at the first analogy that feels right. The situation feels familiar because elements of it resemble the past. But the combination of elements is new, which means the confident analysis is, at best, a starting point and, at worst, a trap.

I asked Duggan what he most wishes the general public understood about strategic intuition.

“The difference between expert and strategic intuition,” he said. “The persistence of the language of ‘instinct’ as a form of decision-making is a sign that the new science of the mind has not yet spread beyond neuroscience.”

We are, in other words, running the most consequential leadership decisions of the century through a frameworkof instinct, gut feel, good judgment, decisiveness that neuroscience abandoned thirty years ago. The science says there are two different cognitive processes that both feel like “instinct,” and one of them is a trap when the situation is genuinely new. The public conversation doesn’t have this distinction. The leaders making the decisions may not have it either.

Organizations Don’t Think

There is a corollary to all of this that applies to organizations. I asked Duggan whether strategic intuition can operate at the institutional level, whether a company or a government can develop it collectively. His answer was five words: ‘Organizations don’t think. Only people do.’

An organization can adopt a method that makes strategic intuition more likely. But the flash itself, the recombination, the glance, happens in a single mind or it doesn’t happen at all. No restructuring, no turnaround playbook, no all-hands address can produce it. Which may be the most precise diagnosis available of what went wrong at Dentsu, and what is going wrong at Nike: not a failure of execution, but the absence of the cognitive event that execution is supposed to serve.

Duggan can’t tell us whether any specific leader is operating on expert intuition or strategic intuition. He was clear about that from the start. But he can tell us what the conditions for strategic intuition look like. And he can tell us what the trap looks like. And he can give us a framework for asking better questions about the leadership decisions shaping the world right now. Not ‘Is this leader a genius or an idiot?’ but ‘Is this leader operating in conditions where strategic intuition can function? Do they have the depth of precedent the mechanism requires? Are they searching, or are they relying on what they already think they know? Can they identify the specific examples that produced their decisions?’

Those are better questions. And the answers, when they come, will not arrive as instinct. They will arrive as search.

Because the most dangerous thing in leadership isn't bad strategy. It's the wrong kind of good instinct.

/ jgs

John G. Singer is the founder and Executive Director of Blue Spoon and the author of When Burning Man Comes to Washington: A Field Manual for Riding Chaos. Hardcore Zen is published weekly on Substack.