How to Navigate a Fallible World

Learn how to move from blind execution to the "Inquiry Loop," creating a safe-to-fail culture where errors are treated as valuable data for the next experiment.

So far in this series of posts we have discussed the following:

  • Our organisation is an entangled mesh of people and things (apparatus).

  • We shape it by cutting reality with constraints.

  • We are morally responsible for the reality we create.

However, the cuts we design are often clumsy and we get it wrong. Our constraints are often too tight or too loose. We build an apparatus designed for efficiency and accidentally create burnout. We design for innovation and get chaos.

How do we survive our own fallibility? We can turn to the philosophy of Pragmatism.

The End of the ‘God Complex’

Traditional management behaves like a religion. The Leader (High Priest) receives a Vision (Strategy) from above. They hand down Commandments (Policies) to the believers. If the plan fails, it is because the believers lacked faith (or ‘execution discipline’).

Pragmatism, rooted in the work of Dewey, James, and Peirce, demands we burn this church down. In Pragmatism, there are no absolute truths. There are only hypotheses.

  • Your strategy is a guess.

  • Your org chart is a bet.

  • Your new software is an experiment.

The organisation is not a machine to be driven or directed; it is a Community of Inquiry. It is a giant laboratory where everyone’s job is to test whether the apparatus is working and whether the outcomes we want are materialising.

Truth is Consequence

How do we know if our apparatus is ‘true’? Pragmatism gives us the maxim: Truth is what works.

You can have the most beautiful, eloquent, expensive strategy deck in the world. But if the consequence of that strategy is that customers leave and employees quit, the strategy is false. Conversely, if a messy, ugly, unwritten habit in the warehouse solves the shipping problem every time, that habit is true. This shifts us from ‘compliance’ (did you follow the rule?) to ‘consequence’ (did the rule produce value?).

The Pragmatic Cycle

If the organisation is a lab, how do we run it? We stop executing blindly and start inquiring. When we face a problem or an indeterminate situation we run the inquiry loop:

Observe the phenomenon (Agential Realism)

Look at the entanglement. Do you know who/what is involved?

Observation: "The decision stalls because the ‘Approval Form’ (Material) requires 4 signatures (Constraint)."

Hypothesise a New Constraint (Juarrero)

Based on the observation, how could we change the constraint regime and the apparatus to improve the situation?

Hypothesis: "If we remove the form and replace it with a ‘Spending Cap’ (Governing Constraint) of £500, speed will increase without breaking the budget."

Run the Experiment (Action):

We treat the experiment as a probe.

A probe is the smallest, most direct action you can take to begin transforming an uncertain situation into one that is more determinate. It’s not meant to be a comprehensive experiment aimed at uncovering universal truths. Instead, a probe is a deliberate, operational step designed to elicit a response from the environment, providing the first tangible insight on which to build understanding. Think of it as sending a small drone into foggy terrain to map the landscape, test the wind, and find stable ground rather than ploughing ahead and building a bridge.

For example, "Team A will try this new constraint for 2 weeks."

Measure the Consequence (Inquiry)

Did speed go up? Did fraud occur?

If it worked, the new constraint becomes the new ‘Habit’. If it failed, we adapt or discard it.

The Culture of ‘Safe-to-Fail’

This only works if you have psychological safety. In a ‘God Complex’ organisation, reporting failure is heresy. In a ‘Community of Inquiry’, reporting failure is data. If a team runs an experiment and it fails, they have generated knowledge. They have proven that this specific arrangement of the apparatus is false. That is valuable.

The leader becomes the Head Scientist (or Gardener) tending to a complex, evolving system. You build the apparatus. You watch what it produces. You measure the consequence. And you repeat, forever.

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Previous

The Apparatus Audit

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Next

The Ethics of Entanglement