Karl Weick: “life is understood backwards but lived forwards.”

The Art of Sensemaking

Your organisation has a learning strategy, it has post-implementation reviews, lessons-learned in confluence (good luck finding it), communities of practice, and maybe a “knowledge management” platform. It believes, fundamentally, that learning is something that should happen before you act. So you can act ‘better’.

Karl Weick spent his career demonstrating that this is backwards. We do not think and then act. We act, and then we make sense of what we did. Learning is not the precursor to action, it is the retrospective interpretation of action that has already occurred. The organisation that waits until it has “learned enough” before acting on AI will never act at all, because most likely some of the learning it needs can only come from action it has not yet taken.

Weick’s body of work is vast, spanning sensemaking theory, enactment, organising processes, high reliability, and a philosophically rich account of how meaning is constructed in organisations. His collaboration with Kathleen Sutcliffe on mindful organising alone could fill a series. This short post focuses on the core insights most directly relevant to anyone leading organisational change today, particularly in the context of AI adoption.

1. The Great Reversal: Action Precedes Understanding

As we have discussed, traditional management logic assumes a linear sequence: Analysis → Strategy → Execution. Gather the data, formulate the plan, implement the solution. Weick argues this is a fallacy. In complex environments, you cannot analyse your way to the truth because the truth is emerging from your actions.

Weick summarised this with the phrase:

“How can I know what I think until I see what I say?”

It is, in my view, a description of how cognition works in practice (wait for when we discuss Wittgenstein). You discover what you believe by observing what you do — and what you do changes the situation you are trying to understand. Thought and action are not sequential phases. They are interrelated and mutually constitutive.

This is the cognitive mechanism behind Snowden’s Cynefin “Probe-Sense-Respond” loop. See a brief discussion of this in the link below.

Dave Snowden, Cynefin, and the Table Napkin Test

You must act (probe) to generate the reality that you can then interpret (sense). Ralph Stacey argues that a strategic plan is a “gesture” made from within a web of interaction. Weick explains what happens next though —> the meaning of that gesture is only discovered retrospectively, based on the responses it elicits. You do not know what your AI strategy means until you see how the organisation responds to it.

For transformation leaders, this reversal has an immediate practical consequence. The organisation that commissions a twelve-month AI readiness assessment before taking any action is not being prudent. It is performing the appearance of learning while systematically preventing the only kind of learning that matters: the learning that comes from doing something and paying close attention to what happens.

2. Enactment: You Create the Environment You Complain About

Most organisations treat their environment (the market, the competitive landscape, the regulatory context, the “culture” ) as an external reality they must analyse and adapt to. Weick argues that this is a fundamental misunderstanding. We enact our environments. We create the constraints we face through our own actions, attention, and language.

Consider the organisation that approaches AI adoption through extensive governance. It creates an AI approval board, a risk assessment framework, a mandatory review process for every use case. These structures were designed to manage risk, but they enact a particular environment; one in which AI is possibly dangerous, experimentation is suspect, and the default answer is likely “not yet.” The leadership team then surveys the organisation and finds that people are cautious, resistant, and slow to adopt. They conclude that the culture is the problem. Weick would say, “you created that culture.” The governance apparatus enacted the very resistance it was supposed to overcome. To be clear, that doesn’t mean you don’t need any governance. The idea is that the governance framework needs to evolve as we respond.

Chris Argyris: The Trap of “Skilled Incompetence"

This directly extends Chris Argyris’s analysis of defensive routines. If a leadership team acts with secrecy and defensiveness, what Argyris calls Model I behaviour, they enact an environment of mistrust. Anthony Giddens would describe this as the duality of structure where, for instance, a governance framework both constrains and enables action, and the people who created it are simultaneously constrained by the very structures they produced.

The implication for transformation is clear: stop treating “culture” as an external obstacle to be overcome. You are co-creating that culture in every meeting, every policy decision, every communication. If you want to change the environment, you must change your own gestures because, as Stacey would remind us, those gestures are all you have.

3. Retrospective Coherence: The Trap of the Clean Narrative

Weick warned that,

“life is understood backwards but lived forwards.”

When we look at a successful transformation we usually strip away the confusion, the luck, the wrong turns, and the failed experiments to create a clean, linear narrative. First we did A, which led to B, which enabled C. The story is compelling. It is also largely fictional.

This is the mechanism by which “best practice” becomes dangerous. What looks like a brilliant strategy in hindsight was likely a series of messy probes and sensemaking moments in real-time. The people involved perhaps didn’t know it would work. They were acting under uncertainty, interpreting ambiguous signals, and adjusting as they went. Whatever their powerpoints said.

Your “lessons learned” are also contaminated by outcome knowledge - knowing how it all turned out. The post-implementation review that identifies “what went right” is constructing a retrospectively coherent narrative, not recovering the actual process of discovery. Be deeply suspicious of AI transformation case studies. The vendor who presents a seamless adoption journey is selling you a retrospective narrative, not a methodology you can replicate.

4. Dropping Your Tools: Identity as a Barrier to Learning

In his famous analysis of the 1949 Mann Gulch fire disaster, Weick noted that firefighters died because they refused to drop their heavy tools to run faster from an advancing blaze. Why? Because without their tools, they were no longer firefighters. Their identity was bound to their equipment. To drop the tools was to lose not just weight but self.

Under transformation, organisations cling to their own “heavy tools” - legacy reports, obsolete metrics, governance rituals, architectural review boards - even when these tools actively impede survival. I really love this concept of us all having heavy tools we feel we need to carry. The weekly status report that nobody reads. The stage-gate process designed for a world where code was written by hand. The architecture review that adds three weeks to every initiative. Everyone knows they are obstacles. Nobody stops them. Because stopping them would require someone to say: “This thing I have spent my career perfecting is no longer necessary.” And that is an identity loss, not a process change. Or rather, when they do try to stop them, the owner of the process fights back hard. As if they are fighting for their very identity.

This connects to Stacey’s insight that anxiety is at the centre of why transformations stall. The question people are actually asking is not “Is this new approach better?” but

“Am I still competent?” and “Do I still belong here?”

When you tell a senior architect that their role is evolving from designing systems to writing specifications for AI agents, you are asking them to drop their tools. The resistance that follows is not irrational, it is the entirely predictable response to having your professional identity disrupted.

5. Small Wins: The Strategy of Plausible Progress

Weick proposed the concept of small wins as a strategy for tackling problems that feel overwhelming. The idea is deceptively simple; instead of framing the challenge as a massive transformation programme, recast it as a series of achievable experiments. Each small win is concrete, visible, and within reach. Each one changes the conditions for the next. This is well explained and used by Snowden too. It is grounded in Weick’s sensemaking theory. People cannot make sense of abstractions so they ‘make sense’ of events that are specific, tangible things. A forty-page AI strategy document does not create sensemaking, it creates anxiety. But a team that used an AI agent to generate a working prototype in an afternoon IS an event. People can see it, talk about it, argue about it, and learn from it. It changes what feels possible.

Seligman’s research on learned helplessness reinforces why this matters. When people repeatedly experience a lack of control - when transformation programmes are imposed, when their input is ignored, when they see no connection between their effort and any outcome - they stop trying. Small wins restore the connection between effort and outcome. They are the antidote to the learned helplessness that accumulates from years of failed change initiatives.

6. High Reliability: Learning by Preoccupation with Failure

Weick’s study of High Reliability Organisations (HRO’s) like aircraft carriers, nuclear plants and wildfire crews, revealed that they do not succeed because they have better plans. They succeed because they have a preoccupation with failure. They treat every small anomaly, every weak signal, as a potential symptom of a systemic issue. They do not explain away near-misses; they investigate them.

Weick identified five principles of mindful organising:

• Preoccupation with failure,

• Reluctance to simplify interpretations,

• Sensitivity to operations,

• Commitment to resilience,

• Deference to expertise.

All of these are relevant to transformation. But deference to expertise is key. In HROs, when a crisis occurs, decision authority migrates to the person with the most relevant expertise, regardless of rank. The admiral defers to the petty officer who understands the specific system that is failing. Hierarchy is maintained in routine operations but relaxed when expertise matters more than authority.

This is the operational heartbeat of what Westrum (coming soon!) calls a Generative Culture. In pathological cultures, weak signals are ignored or punished. In bureaucratic cultures, they are processed through channels. In generative cultures, they are amplified and anyone who notices something wrong is empowered to raise it, and the organisation treats the signal as a gift.

For AI transformation, the HRO principles offer a diagnostic: when a team discovers that their AI-generated code contains an error, what happens? In a pathological culture, the error is used as evidence that AI is dangerous and should be restricted. In a bureaucratic culture, it triggers a new governance requirement. In a generative culture, it triggers curiosity. “What does this tell us about our specifications? What did we fail to make explicit? How do we improve the feedback loop?”

Response to an anomaly reveals the culture. And the culture determines whether the organisation learns or merely reacts.

---

(An Organisational Prompt is something you can do now…)

Organisational Prompt

Weick argues that in times of uncertainty, plausibility is more important than accuracy. You do not need a map that is perfectly accurate; you need a map that is good enough to get the team moving, because movement generates the data you need to correct the map.

Identify one AI use case in your organisation where the team is waiting for “more information” before proceeding. Write a one-paragraph story - not a business case, not a specification, just a story - of what success might look like in three months. Make it plausible, not precise. Then ask two questions: “What is the smallest thing we could do this week to test whether this story is heading in the right direction?” and “What signal would tell us the story needs to change?”

The point is not to get the story right. The point is to get the team acting. Because action is the only thing that generates the sensemaking data you need. A plausible story that produces movement is worth more than an accurate analysis that produces paralysis.

---

Further Reading

Karl Weick: Sensemaking in Organizations - The foundational text on how organisations construct meaning. Dense but essential. Every page rewards careful reading.

Karl Weick: The Social Psychology of Organizing - Where the enactment theory is developed most fully. Weick’s argument that organising is a verb, not a noun, starts here.

Karl Weick and Kathleen Sutcliffe: Managing the Unexpected - The practical application of high reliability principles to everyday organisations. The most accessible entry point to Weick’s work.

Karl Weick: “The Collapse of Sensemaking in Organizations: The Mann Gulch Disaster” - The essay on dropping your tools. One of the most cited papers in organisational studies, and one of the most readable.

Disclaimer

I write about the industry and its approach in general. None of the opinions or examples in my articles necessarily relate to present or past employers. I draw on conversations with many practitioners and all views are my own.