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When Iceberg Is Melting Meets Sisyphus And the Failure Mode of AI Strategy

When Iceberg Is Melting Meets Sisyphus And the Failure Mode of AI Strategy

A Simple Story That Is Not Simple at All

On the face of it, John Kotter’s Our Iceberg Is Melting is a simple tale of a group of penguins who are scared about losing their home, their iceberg, and yes, even more scared of the changes that could entail. But through that simple story and their struggle to find a new home, it delivers a far more powerful message, one that feels increasingly relevant for companies today as they set strategies that no longer align with changing market and internal realities.

The Story and the Cast of Characters

Fred: The story begins with Fred, an unusually observant, curious, and creative penguin. Fred, using his powers, notices that their iceberg, their home, is melting. Not one to simply wait for his daily quota of squid, he speaks to one person in the leadership council who he feels might actually listen.

Alice: Enter Alice, one of the leaders of the colony, practical and tough. Of course, Alice initially wonders whether Fred perhaps missed his morning fish meal. But she gives him a patient hearing, which rapidly turns to alarm when she sees the data for herself, the cracks and fissures spreading across their iceberg. Alice brings Fred’s concern to the leadership council, and this is where the rest of the cast enters.

Louis: Formal colony leader, well respected and deeply conservative. Possibly the senior leader of any company, not just a colony of penguins.

NoNo: One of the colony leaders who keeps trying to poke holes in Fred’s theory. We do not need to look far for the NoNos. They are typically conspicuous by their alarming presence and doomsday predictions, usually while sipping coffee at the office watering hole.

Buddy: Well liked, influential, but not very powerful.

The Professor: The intellectual influencer.

Scout: Helpful, excited, and part of the change. Sally Ann Equally excited and supportive of moving forward.

The unlikely team of penguins eventually waddles its way to a solution, enjoying quite a few squids along the way, while showing the real lessons on the long road from strategy to change to execution. Now let's enter today's boardrooms, keeping this story in mind:

Strategy in the Age of AI and the Danger of Prompt Strategy

Strategy has always been about making the right choices, no matter how uncertain the future might be. In the age of AI, however, strategy continuity carries a new risk, particularly when strategy starts getting generated and regenerated through independent prompts by different teams. Planning cycles begin to resemble ten-minute deliveries. The danger here is twofold.

The First Danger: Lost Organizational Memory

Organizations run the risk of accumulating faster outputs while losing the narrative. Strategy depends on operational memory, on teams understanding why something was decided, what choice points made it critical, and how those choices remain relevant or need to adapt as markets, technologies, and operating environments change.

Without this, everything becomes more disparate. OKRs drift from team priorities. Priorities drift from reviews. Over time, the breakdown in narrative alignment shows up as busy work without direction.

The Second Danger: Strategy Stops Feeling Real

Second, and even more critically, strategy has to transcend multiple levels of the organization to feel real. This means more than aligning on goals. This is where strategy becomes story. Not story as language or narrative flair, but story as structure. A structure that allows reasoning to survive time, turnover, and uncertainty.

Imagine telling the story of Iceberg Is Melting to a team on the cusp of a merger and then aligning them around the new strategy and the changes that must be made, individually and collectively. That is where strategy moves from the boardroom to the trenches of real growth and action.

Why This Is Becoming Urgent Now

One of the most enduring images from Greek mythology, at least for me, is that of Sisyphus, condemned to push a boulder up a hill forever. Each time he nearly reaches the top, the rock rolls back down and he has to start all over again. This image is often shared as an example of resilience and grit.

But in the context of organizational strategy and growth, a different meaning emerges. The punishment Sisyphus faced went deeper than effort. It was the fact that nothing accumulated and every push reset the starting point back to zero. This detail matters.

At stotio , we call this the Sisyphian strategy failure mode, where decisions get made but the logic that produced them fades, and teams inherit outcomes without context. That is the danger of prompt driven strategy in the age of AI.

And this iceberg again needs Freds who can spot what is melting and how to save it.