In 1967, a Maltese physician and psychologist named Edward de Bono published a book titled New Think: The Use of Lateral Thinking. He had recently coined the term “lateral thinking” — a phrase that would, over the next half-century, become one of the most quoted pieces of management vocabulary in the English language.
The Oxford English Dictionary added it. Business schools built curricula around it. Thousands of corporate training programs used it.
Most of them missed the point.
De Bono spent the rest of his life — he died on June 9, 2021, at the age of 88 — trying to explain what he actually meant. He wrote more than 60 books. He consulted with governments and corporations across forty countries. He developed the Six Thinking Hats methodology, the Po provocation technique, and dozens of other tools.
But the core idea, the one that mattered, can be compressed into a single sentence he repeated in interviews and books for fifty years:
“You cannot dig a hole in a different place by digging the same hole deeper.”
This piece is about why that sentence is, in my opinion, the single most useful piece of career advice available to any senior leader navigating AI transformation in 2026 — and why almost nobody is actually applying it.
What de Bono was actually saying
The standard reading of de Bono is that “lateral thinking” means creative problem-solving. Think outside the box. Try unconventional approaches.
That reading is true but shallow. The deeper insight is about how the human mind works.
De Bono’s central claim was that the brain is, fundamentally, a pattern-recognition and pattern-following system. When you encounter a problem, your mind doesn’t reason from first principles. It rapidly retrieves the most familiar framework for dealing with similar problems and routes your thinking along that established pathway.
This is enormously efficient. It is also enormously limiting. Because the most familiar pathway is not always the most productive one.
De Bono called the conventional logical approach vertical thinking. It moves step by step from one premise to the next, deeper along an established pathway. It is the dominant mode of analytical reasoning that schools, professions, and corporations have been training for centuries. It is excellent for problems where the right pathway has already been identified.
He contrasted this with lateral thinking. Rather than digging deeper along the established pathway, lateral thinking deliberately steps off it and approaches the problem from a different angle, generating alternative entry points that vertical thinking would never encounter because they lie outside its trajectory.
The famous quote — “you cannot dig a hole in a different place by digging the same hole deeper” — is the compressed expression of this distinction. If the gold isn’t where you’re digging, no amount of additional vertical effort will produce gold. The only useful move is to stop digging and start somewhere else.
The five-feet-of-dirt problem
The analogy de Bono used to make this land with non-academic audiences was specific and visual.
Imagine you’re digging for gold. You’ve gone five feet down. No gold.
What do you do?
The intuitive answer for almost everyone — and especially for anyone trained in American business culture — is to dig faster. To intensify the effort. To bring in more shovels. To work the night shift. To execute relentlessly.
Sometimes this is right. If you have good reason to believe the gold is at ten feet, dig faster. If you’re in the right hole, the answer is more depth.
But sometimes — and de Bono argued, more often than people are willing to admit — the trouble isn’t that you’re digging too slowly.
The trouble is that you’re digging in the wrong place.
The instinct to dig faster, when you’re in the wrong place, is not just useless. It is structurally counterproductive. It uses up the energy, attention, and capital you would need to dig somewhere else. It deepens your investment in a location that isn’t going to pay out. It produces the appearance of progress without any of the substance.
This is the problem de Bono spent five decades trying to surface for executive audiences.
His repeated diagnosis: in business, in politics, in personal life, the dominant failure mode is not laziness or insufficient effort. It is highly competent vertical thinking applied to the wrong hole.
The personal observation that surfaces the framework
There is an observation about senior leadership that I think is one of the most underexamined experiences in modern executive life.
When I’m in the right context, I feel incredibly smart and capable. When I’m in the wrong context, that feeling disappears.
This is one of the sharpest articulations of an executive insight available, and it points directly at the de Bono framework.
The implicit promise of senior leadership, the way most executives have been taught to think about themselves, is that competence is portable. You are smart, or you aren’t. You are capable, or you aren’t. The capability travels with you across contexts because the capability is yours.
De Bono’s framework, supported by half a century of cognitive research that has confirmed his original intuition, says this isn’t true.
Capability is largely a function of context.
When the context matches the patterns your mind has been trained on, you appear — and feel — extraordinarily capable. The pattern-recognition system retrieves the right framework, the right vocabulary, the right judgment, the right examples, and routes your thinking productively. You make good decisions. You see things others miss. You feel sharp.
When the context shifts — when the problem doesn’t match the patterns you’ve trained on — the same brain that felt sharp now feels slow. You hesitate. You second-guess. You feel obsolete or out of your depth.
This is not a failure of intelligence. It is a structural feature of how the brain works.
For senior leaders, the implication is enormously liberating if you’re willing to accept it: when you feel less capable than you used to, you are not necessarily becoming less capable. You may simply be in the wrong context. The capability hasn’t gone anywhere. The patterns you trained for thirty years are mismatched with the patterns the new context demands.
The de Bono move, in this situation, is not to work harder at being capable in the wrong context.
The move is to change context.
Why this matters specifically in 2026
The reason I think this framework is the single most useful piece of career advice for senior leaders in 2026 is that the AI transformation is, for almost every senior executive I work with, a context shift.
The patterns they trained for thirty years — the patterns that made them feel incredibly capable in 2018, 2019, 2020 — are mismatched with the patterns the AI-augmented world demands.
The CMO who spent twenty years mastering brand strategy is sitting in meetings where AI is producing brand strategy in seconds.
The senior consultant who built her career on synthesizing complex client situations into clear strategic decks is watching clients use AI to produce equivalent decks in 90 seconds.
The CIO who spent his career mastering enterprise architecture decisions is being second-guessed by junior engineers using AI tools he doesn’t fully understand.
The CFO whose value was built on producing financial analysis from scarce data is operating in a world where data is infinite and analysis is automated, and the constraint has shifted to judgment, which is exactly the part of his role he most assumed would always be his.
Every one of these leaders has, by every objective measure, retained their underlying capability. They are not less intelligent than they were five years ago. They have not lost their experience, their judgment, their networks, their credentials.
They are digging in the wrong hole.
And every instinct trained by thirty years of corporate culture — the lean-in instinct, the execute-relentlessly instinct, the double-down instinct — is telling them to dig faster.
The de Bono diagnosis says this is precisely the wrong move.
The right move is to stop digging where they’ve been digging and move to a different location.
The sunk cost of the deep hole
The reason this is so hard to do, in practice, is that the hole you’ve been digging is deep. It represents twenty or thirty years of accumulated expertise. Credentials. Network. Identity.
When de Bono says “move to a different hole,” he is asking executives to walk away from a hole that took them their entire career to dig.
That feels, viscerally, like wasted effort.
It isn’t.
The capability that produced the depth of the old hole — the discipline, the pattern recognition, the judgment, the willingness to work hard at something for years — is the same capability that will produce the new hole. Faster. In a better location.
But you have to be willing to leave the depth behind.
This is, in my coaching experience, the hardest single conversation a senior leader has to have with themselves. Because the sunk cost feels enormous. The identity is bound up with the depth. The professional reputation rests on the depth. And the new hole, by definition, is shallow.
Most senior leaders, faced with this choice, choose to dig their existing hole deeper. They tell themselves the gold must be at fifteen feet, or twenty feet, or thirty. They redouble. They lean in. They execute relentlessly.
They produce, in some cases, the deepest hole in their industry.
And they fail anyway, because there is no gold there.
The de Bono framework is the diagnostic that surfaces this failure mode before it becomes terminal. Not by criticizing the depth of the hole — the depth was real, the effort was real, the expertise is real. But by asking the question that vertical thinking is structurally unable to ask:
Is this the right hole?
What the lateral move actually looks like
The misreading of “lateral thinking” that has dominated business culture is that it means radical creative reinvention. Quit your career. Start a band. Move to Bali.
That’s not what de Bono meant, and it’s not what the framework requires.
A lateral move, in the de Bono sense, is a sideways shift that preserves the underlying capability while changing the location of the work.
The CFO doesn’t quit finance. She shifts from producing analysis to designing the AI-augmented decision architecture that produces analysis. Same financial judgment, different hole.
The CMO doesn’t abandon brand work. He shifts from producing brand strategy to orchestrating an AI-augmented creative process that produces brand strategy. Same taste, different hole.
The senior consultant doesn’t leave consulting. She shifts from being the analyst who builds the decks to being the orchestrator of AI-assisted client engagement. Same client intuition, different hole.
The CIO doesn’t abandon technical leadership. He shifts from architecting systems to architecting the integration of AI into systems. Same architectural judgment, different hole.
In every case, the capability that produced the depth of the old hole transfers. The new hole isn’t a betrayal of the career — it’s a continuation of it, in a location where the underlying capability can still compound.
The leaders who recognize this in 2026 will be the leaders who define the next decade.
The leaders who keep digging the old hole, however deep, will spend the next decade wondering why their effort is producing diminishing returns while less talented peers seem to be effortlessly moving ahead.
The less talented peers aren’t more talented. They’re in a different hole.
Three practical questions
If you want to actually apply the de Bono framework to your own career in 2026, three questions are worth sitting with.
One: what is the central pattern around which your senior career has been built?
Not “leadership” or “strategy” — these are too abstract to be useful. The actual concrete pattern. The specific kind of problem you have spent the last decade getting good at solving. The recurring situation in which you feel most capable, most confident, most valuable.
That pattern is your hole. Identify it precisely.
Two: has the value of that pattern changed in your industry in the last three years?
Be honest. Not whether you still find the pattern useful — whether the market still rewards that pattern at the price it used to. In some industries the pattern is still valuable. In many, the price has quietly collapsed because AI now produces the same pattern at a fraction of the cost.
If the answer is “the price has collapsed,” you are still digging at five feet. The gold has moved.
Three: what lateral move preserves your underlying capability while changing the location of the work?
Not a complete career reinvention. A sideways shift. The same expertise applied to a different problem, where the value is still compounding. Where the pattern you’ve trained on is still rare and useful.
That’s the lateral move. It will feel uncomfortable. The new hole will be shallow for a few years. The depth will take time to rebuild.
But the alternative is digging the old hole deeper, in a location where there is no longer any gold.
The closing thought
There is a phrase from de Bono’s later work that I want to close with, because it captures something his motivational-poster admirers usually miss.
He wrote, in I Am Right, You Are Wrong (1990), that the deepest problem with conventional intelligence is not that it produces wrong answers. It is that it produces highly competent answers to questions that should have been asked differently.
“It is not enough to do your best; you must know what to do, and then do your best.”
That is the framework, compressed.
The American business culture of the last forty years has been overwhelmingly focused on the second half of that sentence. Do your best. Execute relentlessly. Work harder. Lean in. Double down.
The first half — know what to do — has been quietly underweighted, because it is harder to teach, harder to measure, and harder to perform publicly.
You can show effort. You can’t easily show that you’ve correctly identified which hole to dig.
The AI transformation is forcing the first half back into the center of executive practice. Because in 2026, executing relentlessly on the wrong hole produces nothing. The pattern that worked five years ago has, in many domains, no longer the right pattern to be reinforcing.
The leaders who will define the next decade are the ones who, right now, are asking the harder question.
Am I in the right hole?
If the answer is yes, dig harder. Use every ounce of accumulated capability to go deeper.
If the answer is no, stop.
Move sideways. Start a new hole. Trust that the capability that produced the depth of the old hole will produce the new one, in a better location, with the years you have left.
De Bono spent fifty years teaching this. Most people who quoted him missed the point.
In 2026, with AI rewriting the location of value in almost every senior career, the point is no longer optional.
You will not feel as capable in the new hole, at first. The shallow depth will feel like regression. The familiar patterns of the old hole will keep pulling at you.
That feeling — the wrong-context feeling — is the most important piece of executive information available to you right now. It is the signal that the hole has changed.
The discipline is to read the signal honestly, to stop digging, and to start somewhere else, while you still have the energy to make the depth count.
The world has changed. The leaders who notice will be the ones the next decade is built around.
