It was around 15 years ago that I first came across a line by Professor Robert Spillane, long-time philosopher at Macquarie Graduate School of Management, that stayed with me long after I had forgotten most of the context in which I read it. He said, “I teach philosophy in the hope that it will be applied to management and psychology, and in the hope that it will not.” It is the sort of paradox that, if you allow proper time to think about it, begins to unveil something elegant. Spillane I think is alerting managers to resist rushing into reducing complex philosophical concepts into ‘ready to go’ management tools. Instead, philosophical constructs should guide how we think about our work. 

That line found its way from back of my mind recently when I was helping a client elevate their strategic processes.  More specifically, the curious truth that behind every business failure lies a strategy. Not one designed to fail, but one once embraced with optimism and confidence. When things go wrong, most post-mortems focus on what happened in the immediate past, perhaps in the last plan or two. Rarely do we look further back. The unspoken assumption is that strategies from fifteen or twenty years ago are too remote to be relevant. The markets were different, the technology was different, the leadership was different. That was then; this is now. That’s the conventional wisdoms mantra.

But this assumption may be the first sign of shallow strategic thinking. An anthropologist learns early to resist the lure of the “now” as the only reality worth studying. Cultures carry their past within them. Patterns of thought, the metaphors that shape our stories, the values that determine what we ignore and what we celebrate. These change far more slowly than market conditions. The same is true in organisations. Beneath the fresh branding and the new strategic frameworks, much of the underlying thinking is amazingly persistent. What changes most is the language in which it is dressed.

I sometimes think of this as strategic archaeology, that is, the work of digging down through layers of past strategies to see what still lies there, embedded in the organisation’s cognitive soil. And from there, perhaps, to what we could call a kind of ‘strategic autopsy’. Laying out a series of plans from across two or three decades and asking not simply why they succeeded or failed, but what enduring assumptions they reveal. Which metaphors keep reappearing? Which blind spots survive every leadership change? Which cultural drivers seem immune to the urgency of the present moment? Complexity thinking teaches us that systems carry memory. The past is not dead matter but a living pattern, shaping what is possible in the future.

It is tempting to believe that the past is a foreign country whose customs we have outgrown. This belief is comforting because it absolves us from confronting the possibility that our present thinking is not so different from the thinking that shaped decisions long ago. Yet time and again, when we look closely, we are likely to detect similar gravitational pull at work. Familiar ways of framing problems, recurring patterns in how we assign faults or credit. There is almost instinctive return to certain strategic paradigm and habit when the pressure is on.

A strategy, in this sense, is more than a document; it is an artefact of thought. Like any artefact, it carries the marks of the people and the culture that produced it. In twenty years, a business might produce four or five major strategic plans, each shaped by different circumstances, but all sharing a certain resemblance. The leadership may not notice this resemblance, and may even prefer not to, because it disrupts the comforting narrative of progress. Or as the case often is, leaders want to create a distance between past and present they are mandated to steer. And so, the real opportunity for learning is lost in the rush to be seen to act.

The idea of what I’d call “20-year strategic autopsy” is grounded in that observation. It is not about getting bogged down in the details of outdated objectives or obsolete market data. It is about laying these past strategies side by side and asking: what do they reveal about how we think?  Which patterns persist despite the seemingly infinite churn of events? Where did our strategic imagination narrow over time, and where did it open? This is less a forensic investigation than a slow reading of our own intellectual and cultural history. It asks us to pause and apply what philosopher Martin Heidegger named ‘Gellasenheit’. Roughly translated, allowing things to show themselves before we impose our frameworks or seemingly logical solutions.  By doing that we are more likely to glean some of the drivers of past failures may still be quietly shaping our decisions today.

Complexity thinking makes this work both necessary and humbling. In a complex system, change is not simply a matter of input and output. History matters. Initial conditions matter, the system has memory. Organisations, just like ecosystems, carry the imprint of past seasons in their structure. Strategies are part of that imprint. A new plan drawn without a deep reading of its predecessors’ risks becoming another layer of sediment that future leaders will dig through, wondering why so little really changed.

There is something anthropological in this approach. In the field, an anthropologist learns to pay attention to the layers beneath the obvious. The ways customs, beliefs, and metaphors endure beneath the noise of daily events. Applied to strategy, this becomes a discipline of patient excavation. It is not nostalgia, nor is it about dwelling on mistakes. It is about understanding the cultural and cognitive DNA that keeps resurfacing in different guises, shaping what we see as possible or impossible.

A strategic autopsy of this kind is not a comfortable exercise. It demands that we move beyond the reflex to forget and replace. But instead cultivate a habit of reflective continuity. It is an act of intellectual humility I think makes us better thinkers. The kind of strategic thinkers ready to admit that the problems we face today may not be entirely new  and that we may have been rehearsing our responses for decades without fully realising it. It’s worth remembering that organisations are cultures. And every new set of leaders come into an existing culture and are shaped by it.  This in turn creates a cultural continuity that is subtle, even undetectable at times, but very real nonetheless.  If this kind of approach is done with care and patience it can become a source of resilience, helping leaders recognise when they are about to walk an old path with new shoes.

Perhaps this is where Spillane’s paradox finds its practical expression. Philosophy, when it seeps into the way we think about strategy, can deepen our awareness of the choices we make and the assumptions we carry. But it resists being reduced to a checklist or a tool in a manager’s kit. It is there in the questions we dare to ask, the patterns we allow ourselves to see, and the histories we are willing to acknowledge as still alive in the present. A “20-year strategic autopsy” is, in that sense, less about the past than about creating the conditions for a future we can approach with clearer eyes.