The Croquet Match: What Alice in Wonderland reveals about dysfunctional cultures

Change Kind
Jan 9
3 min read

Lewis Carroll's Alice's Adventures in Wonderland is often seen as delightful nonsense. However, beneath the rich symbolism there is a linkage to chaos, arbitrary authority, and the dysfunctional systems people navigate daily.

Nowhere is this clearer than in the surreal croquet match: flamingos as mallets, hedgehogs as balls, hoops that wander around the lawn, and a Queen whose rulings depend entirely on mood.

Many professionals recognise this scene not as fiction, but as their workday.

As organisations race to adopt artificial intelligence (AI), believing it will somehow correct inefficiencies and sharpen decisions, it’s worth remembering the lesson of Wonderland: dysfunction is not solved by tools, instead, it is amplified by them. AI introduced into chaos does not produce order. It produces larger, faster, more inscrutable chaos.

Ironically, Carroll himself explores this contrast in the sequel Through the Looking-Glass, a book built on the exact opposite principles. Unlike Wonderland’s randomness, Looking-Glass World runs on rules, logic, and chessboard precision. My next personal goal is to read it specifically because of this contrast: it offers a systems-oriented worldview that serves as a powerful metaphor for what organisations should look like before introducing AI.

But first, let's return to the croquet lawn.

Wonderland's Croquet Match: A perfect metaphor for dysfunction

Carroll's croquet match is system failure made visible. Nothing aligns. Nothing stabilises. Nothing is predictable. And what makes matters worse is that everyone pretends like this is normal! So, let's break this down some more:

Flamingos as mallets: Bent, unpredictable tools

The player's mallets are live flamingos that refuse to cooperate. In dysfunctional organisations, tools behave in the same way in that there is misalignment, constant change, variation by team and workarounds requiring heroic effort.

Introducing AI here only adds another flamingo and this time it is more opaque, expensive and connected to core workflows. And, are the core workflows aligned to what is actually happening?

Hedgehogs as balls: Inputs that behave erratically

In the croquet match, the hedgehogs scurry off, or roll up in the wrong direction. Workplaces do this too as priorities shift mid-sprint, requirements are reinterpreted, datasets contradict each other and decisions reverse depending on who is in the room.

AI cannot stabilise this. It simply internalises the inconsistency and masks it with confident-sounding output. So, the hedgehog or AI runs the risk of still running in the wrong direction.

Moving hoops: Ever-changing goals

The hoops walk around the field, making the concept of "scoring" meaningless. Organisations do this by redefining KPIs, shifting success criteria, altering OKRs to suit a narrative rather than reality.

AI systems rely on stable definitions of success. When these shift, the model trains to the wrong signals, optimises the wrong behaviours, and reinforces the wrong culture.

The Queen of Hearts: Power that overrides process

The Queen's favourite phrase is "Off with their heads!" and this in essence captures her leadership style. Ruling on a whim. In the corporate setting, this represents selective enforcement of rules, political decision-making, unpredictable escalations and fear-driven culture.

AI introduced into a fear-based culture does not democratise decision-making. It becomes another instrument of control. Another way to look at it is "well the model says so" which risks crushing debate.

We can see that through the croquet match truly is a metaphor for dysfunction and adding AI into a workspace has a certain allure to it. However, remember AI pulls dysfunction out of the shadows and into the spotlight at rapid pace.

Shortly we will publish an article where you can learn more about how AI may accelerate the collapse of a dysfunctional organisation.