The word 'strategy' is doing a lot of work it was never designed to do. It appears in job titles, deck headings, workshop agendas, and annual reports. It’s attached to things that are, on closer inspection, plans. And sometimes tactics. Occasionally it’s just a list of activities with a confident font and a timeline.
Strategy has become the label we lazily slap on to thinking we want to sound serious about. That is a problem, because conflating strategy with planning produces a very specific kind of expensive mistake: the mistake of executing beautifully in the wrong direction.
My most recent MA focused on military and political strategy from ancient Greece and Rome, which is a subject most marketing people would find rather disconnected from our day-to-day jobs, yet I would argue that most marketing people should really be thinking about it a lot more. Not because warfare and brand-building share obvious mechanics, but because the strategic thinkers of antiquity were grappling with the same fundamental problems we face today: how do you make decisions under uncertainty, with incomplete information, in environments that resist your attempts to control them? This is not a military problem. It is the only problem strategy ever really addresses.
Thucydides, writing about the Peloponnesian War between Athens and Sparta, understood something that most strategy documents and decks miss entirely. Strategy is not about knowing what you will do. It is about understanding the conditions in which you are operating so clearly, that you can adapt when those conditions change. Which they always do. The plan is not the strategy. The plan is what you do while the strategy is working. When conditions shift, the plan changes. The strategy, if it's any good, tells you how to think about what to do next.
The Athenians had a plan at Syracuse in 415 BC. One with brilliant generals, naval superiority, numerical advantage and detailed logistics. They also had a fundamental misreading of the political environment they were entering, a refusal to interrogate their own assumptions about Sicilian and Syracusan belligerence when under attack, and a public debate back in Athens that had confused enthusiasm for analysis. This was the foundational weakness of direct democracy. The result was the worst military disaster in Athenian history.
The plan was, by most accounts, operationally sound. Yet the strategy was absent. And here we are, nearly two and a half thousand years later, watching the same mistakes being made in marketing via detailed channel plans, precise budget allocations, immaculately crafted creative briefs.
And a total failure to ask what actually has to be true and intimately understood about the competitive landscape, the customer, and the category for any of this to actually work.
Real strategy starts with knowing the terrain, not creating a plan. It starts with the honest questions that tend to be skipped in planning meetings because they are uncomfortable and may not fit neatly into a slide.
What do your competitors actually believe about this market? and where specifically are they going wrong? What are customers doing that they haven't yet found language for? What assumptions are you holding that the evidence no longer supports? What would have to change in the next eighteen months to make your current strategy irrelevant? These are not questions you answer in a two-day planning offsite. They are the questions that determine whether the plan you build is pointing at anything real.
The strongest strategies I've been involved in were written to be tested, not defended. They held a clear hypothesis about the world, named the assumptions sitting beneath it, and built in the mechanisms to identify when those assumptions were failing before the failure became beyond rescue. This is deliberately uncomfortable work; and it requires a leadership team more interested in being right eventually, rather than being right just when everyone’s present in the room — and willing to revisit conclusions when new evidence comes to light.
Sadly, most organisations are not built for this. They are built for consensus, for quarterly reporting cycles, and for the comfort of a document that looks like certainty. Thucydides (or Sun Tzu or von Clausewitz) would have recognised the problem immediately. History’s first proper historian spent twenty-seven years watching what happens when capable and even talented people confuse the quality of their plan for the quality of their thinking. The plan is never the point.
Understanding why it might fail, and what you will do when it does, is where the strategy actually lives.
