AI and getting trapped inside the box

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New tools raise the bar on the need for creative thinking.

Geoff Wilson

A recent essay from AI Snake Oil (here) made a surprising claim: that artificial intelligence might slow down science. Not because it’s inaccurate, but because it’s too good at being accurate–within the wrong frame.

The author points to the centuries-long dominance of the geocentric model of the universe. At one point, predictions of planetary motion based on Earth being the center of the universe were astonishingly precise. But they were also deeply wrong. The math worked. The understanding didn’t.

The essay poses an unsettling idea: if AI had existed then–and been trained on those models–we might have clung to the wrong theory even longer. The system would optimize the pattern, not question the premise.

That idea should raise eyebrows in business, too.

Because if AI has the potential to reinforce flawed scientific models under the guise of precision, what could it do to our strategic and operational models in the business world? Could the efficiency of the tool blind us to the fragility of the box it lives in?

Let’s rewind to the 1990s.

Long-Term Capital Management (LTCM) was an elite hedge fund run by some of the most decorated minds in finance — including two Nobel Prize winners. Their trading strategy was based on elegant models, airtight math, and decades of data. They had accounted for everything — except what had never happened.

When the Asian financial crisis hit, and then the Russian debt default followed, the market behavior fell outside the box. LTCM’s models didn’t break–they simply didn’t apply. Within months, the fund teetered on the edge of collapse, threatening to drag the global financial system down with it.

That story wasn’t about incompetence. It was about conviction–conviction in a model that worked, until it didn’t. A belief in historical precision, at the cost of hypothetical imagination.

Which brings us back to AI.

Artificial intelligence excels at pattern recognition. It’s built to identify structure, predict based on precedent, and optimize for success–all within the observed dataset. But what happens when the next critical insight lives outside the dataset? Or when the market moves in a way it never has before? Or when a first-principles challenge is needed, not a predictive output?

What happens to outside-the-box thinking when the most powerful tools we use only look inside the box?

That’s not a knock on the technology. AI can enhance insight, increase productivity, and surface connections humans might miss. But it’s also a mirror–reflecting what’s been done, not necessarily what should be done next.

In that way, AI can become like the geocentric model: precise in the wrong direction.

Or like LTCM: confidently accelerating toward the edge of a cliff because the GPS has never seen a cliff before.

Strategic leaders–the real kind, the ones who hold the long arc of value creation and risk–can’t afford to outsource the act of questioning. AI can suggest. It can support. But it cannot wonder. It cannot imagine the inverse, the anomaly, the edge case that no one has seen but everyone should fear.

The job of leadership–now more than ever–is to ask: what if the model is wrong?

What if the future doesn’t look like the past?

What if we are right about everything, except the thing that matters most?

Outside-the-box thinking is not a luxury. It is, increasingly, the only kind of thinking that will matter. Because as the boxes get smarter, the need for human insight–uncomfortable, abstract, imperfect insight–only grows.

We should use AI. But we should also stay skeptical. Every model has a boundary. Every dataset has a blind spot. And every organization that overfits to efficiency risks underfitting to reality.

So yes, use the tool.

But keep one eye on the horizon–and one foot out of the box.

What do you think?  How do we keep a foot outside the box?

Michael Collins? Who’s That?

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The spotlight doesn’t reach everyone — but success does.

Geoff Wilson

I was swinging golf clubs with a younger professional recently — a sharp, curious guy early in his career. Somewhere around the 11th hole of virtual golf we faced a Par 5 and discussion of an “eagle” came up.  Since I had just chunked my umteenth shot of the game, I made an offhand comment: “I’m so far away from an eagle, you might as well call me Michael Collins.”

He laughed, politely. But then he asked, “Who’s Michael Collins?”

The question stopped me. Because while it was a reasonable question…it was telling.

Michael Collins, as you may or may not recall, was the third astronaut on Apollo 11. While Neil Armstrong and Buzz Aldrin made history in the Eagle lander on the lunar surface, Collins stayed in orbit, piloting the command module (Columbia, for the record) solo for over 21 hours. He never touched the moon. Never took a famous step. Never delivered a line that would echo through time.

But without him, no one would have come home (coincidentally, the return trip from the moon started on July 21, 1969…exactly 56 years ago).

Collins–orbiting the moon as the loneliest human in the universe–was the one who kept the mission alive while the rest of the world watched the main event. He was critical, and yet largely forgotten.

The moment made me think about how often this happens in business, in leadership, in life.

We celebrate the keynote speaker, not the team that built the deck. We remember the CEO who closed the deal, not the analyst who first spotted the opportunity. We quote the founder, not the engineer who debugged the product the night before launch.

We tend to build monuments to moonwalkers. And we forget about the people who kept the orbit steady.

But if you’ve ever led anything big–a transformation, a turnaround, a product launch, a merger–you know that success is rarely the result of marquee moves alone. It’s the result of many people doing their job well, quietly, persistently, without fanfare. Often, without being asked.

Every great outcome has a few people whose names will never make it into the press release. But take one of them away, and the whole thing wobbles.

I’ve seen executive teams spend months on strategy–and then watched a mid-level operations lead execute the plan better than the leadership ever imagined. I’ve seen project managers, schedulers, executive assistants, even interns, step into chaos and bring order. And I’ve seen those same people go home at the end of the day, not looking for credit–just knowing they helped get it done.

These are the Michael Collinses of our organizations.

They don’t need a statue. But they do deserve recognition.

Leaders look for talent that shines. They also look for talent that supports. They understand that success is not only driven by visionaries, but by role players who turn vision into reality. They know that someone has to keep the engine running while others plant the flag.

And they make sure those people know they’re seen.

So here’s a simple challenge: look around your team. Ask yourself: Who is tending the command module? Who is holding the line while others step onto the stage? And what are you doing to celebrate them?

Because the truth is: Not everyone needs to walk on the moon.

Some people bring you home.

What do you think?  How do unsung heroes factor into your organization’s success?  How do you recognize them?

Recent disasters show the importance of keeping your head on a swivel

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Recent flooding disasters provide grim insight into the importance of remaining risk aware in life and work.

Geoff Wilson

First, an author’s note:  My heart aches for the lives lost and families forever changed by the recent flooding in Kerr County and across Central Texas. These reflections are not a critique of those who paid the ultimate price. They are offered with humility — a reminder that even as we grieve, we can reflect on the role of self-leadership when facing risk, uncertainty, and the unexpected.

Earlier this month, flash floods swept through Kerr County and neighboring parts of Texas. Rivers surged, bridges disappeared, and lives were lost — more than anyone even still yet knows, as recovery crews continue their efforts.

In the aftermath, the questions are surfacing. Could this have been prevented? Was there a breakdown in emergency response? Were there gaps in communication, in leadership, in planning?

Probably yes — to all of the above.

But even as we examine the failures in systems and structures, there’s a quieter, harder truth emerging: some of the deaths came down to risk decisions made at the individual level. Sleeping or camping near a river known for flash flooding. Ignoring the rumble of rain upstream. Trusting the past to be a guide for what the next night would bring. Or, importantly, thinking that somebody else would warn of major life-threatening risks.

It’s easy to point fingers when institutions fail. Harder to wrestle with the reality that self-leadership is the last line of defense. That no matter how well a system is designed — or how poorly — you are ultimately responsible for the risks you take with your own life, or with the lives of young people in your charge.

That’s not victim-blaming. It’s a recognition of agency. And it’s a principle that applies far beyond emergency response.

In organizational life, we often fool ourselves into thinking that risk is someone else’s job. We assume that someone — a finance lead, a risk officer, a committee, a consultant — is modeling the downside. Running the scenarios. Watching the flood gauges.

And then the waters rise.

When strategy falters, when markets shift, when the “one in a thousand” hits — the question isn’t who owned the spreadsheet. It’s who owned the decision. More often than not, the person who feels the full force of a risk realized is the same one who delegated the risk management in the first place.

There’s a lesson here. A call to self-leadership, even in the most structured organizations.

Keep your head on a swivel.

Look beyond the dashboard someone else built. Ask where the floodplain is. Know the signs upstream. And remember that just because a risk is being managed, doesn’t mean it’s being avoided.

This isn’t about paranoia. It’s about presence. Strategic leaders don’t live in a state of fear, but they do live in a state of alertness — especially in domains where the downside lands squarely on their shoulders.

If you’re going to sleep by a river — in Texas or in business — make it a conscious choice. Know the history. Understand the margins. Have a plan.

Because no matter how good the systems are around you, there’s no substitute for awareness.

And when the water starts to rise, you’ll want to be the one who saw it coming — not the one waiting for someone else to sound the alarm.

As of this writing, relief is still needed in the flood-ravaged areas.  WGP has made a donation to the Kerr County Flood Relief Fund, and I hope you will consider doing the same.  Here is a link.

What do you think?  Are there ways to keep your head on a swivel when it comes to business and career risk that deserve discussion?

Pain / Management

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The organizational flinch!

Geoff Wilson

This one comes from reflections over the past year I spent recovering from a total knee replacement.  The procedure and the recovery has been a revelation in not only the true miracles of modern orthopedic technology, but also the slow loss of function that we don’t even notice as we age.

Just two weeks ago, my wife and I hiked 65 miles along the Coast Path in Cornwall, England.  That would simply not have been possible for me a year ago.

For more than 20 years, I’ve dealt with the progressive degradation of a knee that I injured badly in 1996.  I’ve written about that injury and the learning that came with it in a prior blog post here.  The long degradation proceeded to a point last May where a simple 10-step stroll was a puzzle of pain and motion…and to a point where I experienced a prison of pain where sitting or lying still hurt as badly as moving. So, I have experience to share in my recovery from that: once the pain was gone, I had to re-learn how to move in ways my body had “blocked” over the past three decades.

I think there’s leadership learning in that process…

To wit: walk behind an older person in a grocery store and you might notice the pattern: the careful steps, the limited turns, the subtle guarding of motion. It’s not just age at play. It’s memory — the memory of pain. A stiff back, a knee that needs replacement like mine, a hip that talks back after a long day. Over time, the body learns to move around the pain. To manage it. And in managing it, it also limits itself.

What begins as protection becomes pattern. Eventually, the body isn’t moving to avoid pain — it’s simply not moving.

Organizations behave the same way.

Pain, in a business context, rarely arrives as a torn ligament. It comes as a failed initiative. A reorganization that went sideways. A strategy that fell flat. A leader who pushed too hard. An innovation that drained resources without results.

And like the aging body, the organization remembers.

People stop suggesting bold moves. Teams become careful. Risk assessments grow longer. Reviews grow heavier. The organization doesn’t say, “We can’t do this.” It says, “Let’s revisit that in Q4,” or “This feels like a distraction,” or the classic: “We tried something like this a few years ago…”

The organizational flinch is rarely loud. It’s quiet. Respectable. Even rational. But over time, it becomes rigid.

In physical therapy, clinicians often help patients relearn movements they’ve been avoiding — not because the body can’t do them, but because it’s been trained not to. The process is slow, deliberate, and occasionally uncomfortable. It requires the patient to trust the process — and the therapist to know when a movement is worth reintroducing.

Organizations need a similar kind of therapy.

Avoidance can’t be the long-term answer. Avoiding difficult conversations, complex initiatives, or once-burned strategic paths may feel prudent. But prudence can harden into paralysis. And agility — the ability to move, pivot, try, and adapt — fades.

This isn’t to say that pain should be ignored. Quite the opposite. Pain is a signal. It points to stress, imbalance, or real risk. But pain also presents a choice: recover and reengage, or protect and retreat. The latter feels safer in the short term. The former builds resilience over time.

Leaders must become attuned to their organization’s flinches. Not just the big ones — the failed product line or the ghost of a bad acquisition — but the smaller ones, too: ideas that never make it to the meeting, suggestions dismissed with a glance, initiatives that quietly die on the vine.

Ask: Where are we guarding movement? What pain are we protecting ourselves from? And is that protection still necessary?

Because over time, what we avoid becomes what we can no longer do.

And if we want to stay agile — as leaders, as teams, as organizations — we have to be willing to move through the pain. Thoughtfully. Carefully. But decisively.

What do you think?