Book Two · The Art of War

Laying Plans

On the five factors Sun Tzu insists you weigh before you commit to anything.

This is the first chapter-length entry in a series applying Sun Tzu’s Art of War to marketing and search strategy.

He opens the entire text with a claim that sounds almost dramatic out of context — that war is a matter of such consequence to the state that it demands the most careful deliberation before it’s ever undertaken. Then, instead of moving straight into tactics, he spends the whole first chapter on assessment. Five factors. A short list of comparative questions. Nothing about execution yet. He seems to be making a deliberate point: most campaigns are decided before the first move is made, by whether the assessment was done honestly.

I think this is the most commonly skipped step in marketing, and the one whose absence is hardest to diagnose afterward, because a badly assessed campaign and a well-assessed campaign that simply had bad luck look identical from the outside once they’ve both failed.

The five factors

Sun Tzu names five things worth weighing honestly before committing resources to any campaign. Translated loosely out of their original military framing:

The moral law — whether the cause commands genuine, shared conviction, not just compliance. In his framing, this is about whether those following you actually believe in the same aim closely enough to hold together under pressure. In marketing terms, this is closer to internal alignment and belief in the positioning itself. A content strategy nobody on the team actually believes in — the messaging everyone privately thinks is a stretch — tends to fail in ways that are hard to trace back to the actual cause, because it shows up as inconsistent execution rather than a stated disagreement.

Heaven — timing, and forces outside your control that still shape the outcome. Seasons, weather, the passage of time in the original text. In a marketing context, this is closer to market timing: whether the category is ready for the claim you’re making, whether a platform’s algorithm or an AI system’s retrieval behavior is in a state where your strategy actually has room to work, whether you’re early enough to shape a category or late enough that the position is already taken.

Earth — terrain, distances, danger and safety, narrow passes and open ground. This is the actual competitive and structural landscape you’re operating in. Which channels are contested, which are open, where the natural chokepoints are — the handful of search terms or AI-retrieval contexts that actually decide visibility in your category, versus the wide-open ground where competing barely matters because almost nobody’s looking there anyway.

The commander — wisdom, sincerity, benevolence, courage, and strictness, in Sun Tzu’s list. Leadership quality, in short — the judgment and discipline of whoever is actually making the calls. This one translates almost without adjustment. A sound strategy under weak leadership tends to degrade in execution regardless of how correct the plan was on paper, and a mediocre strategy under strong, honest leadership often gets corrected fast enough to still work.

Method and discipline — organization, the chain of responsibility, the management of resources and supply. This is operational reality: whether the team, the process, and the budget can actually sustain the campaign being planned, or whether the plan assumes a level of consistent execution the organization has no track record of actually delivering.

Why these five, and not a tactical checklist

What’s notable is that none of the five factors are tactics. None of them are “which keywords to target” or “what format to publish in.” They’re closer to conditions — the underlying state of things that determines whether any tactic layered on top has a chance of working at all.

This maps onto something I keep seeing in marketing planning: teams jump straight to tactics — the content calendar, the channel mix, the specific campaign ideas — without ever honestly interrogating the five conditions underneath. You can have an excellent tactical plan sitting on top of an assessment nobody actually did. It’s the content-and-Earth problem from the Five Rings series, one layer further back: before you even get to technical foundations, there’s a strategic foundation, and skipping it produces the same kind of invisible failure — a plan that looks sound and quietly can’t work because a condition underneath it was never actually true.

The seven comparative questions

After the five factors, Sun Tzu narrows to something sharper: a set of comparative questions meant to be asked honestly against a rival, not in the abstract. Which side has the more capable leadership. Which has the advantages of climate and terrain. Which enforces discipline more consistently. Which has the stronger forces. Which has the better-trained officers and men. Which administers reward and punishment more consistently.

The point of the exercise isn’t flattery or wishful thinking — it’s a forecast built from comparison, not from confidence. This is worth sitting with, because it’s the opposite of how most competitive assessment in marketing actually gets done. The instinct is usually to catalogue your own strengths and hope they’re sufficient, rather than to genuinely compare, category by category, against whoever you’re actually competing with for attention. A category assessment done honestly might reveal that a competitor’s execution discipline is simply better than yours, even if your positioning is stronger — and that’s exactly the kind of asymmetry worth knowing before committing resources, not after.

Deception, reframed

Sun Tzu makes a claim in this chapter that tends to get quoted out of context — that all warfare is based on deception. It’s tempting to import this directly into marketing as license for exaggeration, but I think that reading misses what he’s actually doing with the idea in context. The deception he describes is about concealing your actual state and intentions from a rival while accurately understanding theirs — appearing weak when strong, appearing near when far — not about misleading the people you’re trying to serve.

The marketing equivalent isn’t lying to your audience. It’s not telegraphing your actual strategy to competitors, not over-explaining your positioning in public before it’s defensible, keeping genuine competitive advantage quiet rather than narrating it in real time. There’s a difference between honesty toward a buyer and transparency toward a competitor, and this chapter is really about the second one.

Calculations made before the campaign

Sun Tzu closes the chapter with an image worth holding onto: that victories are decided in the temple, through calculation, before the armies ever meet — and that the side which makes the most complete assessment beforehand wins, largely independent of what happens once the fighting starts.

I don’t think this is an overstatement. A campaign whose assessment was honest and thorough tends to survive contact with reality reasonably intact, adjusting tactically without needing to abandon the whole premise. A campaign whose assessment was skipped, or done to confirm an answer the team had already decided on, tends to collapse the moment reality diverges even slightly from the plan — because there was no real foundation underneath the plan to begin with, just confidence standing in for one.

What this asks of you before anything else in this series

Every later chapter in this arc — resource discipline, indirect strategy, positioning, momentum, terrain, intelligence — assumes this first one has actually been done. Sun Tzu isn’t being rhetorical when he puts assessment before every other topic. He’s making a structural claim: none of what follows works as compensation for skipping this step.

Practically, this means resisting the urge to jump straight to the exciting part — the campaign idea, the content angle, the channel strategy — before genuinely, uncomfortably answering the five-factor and seven-question versions of: do we actually believe in this positioning, is the timing right, do we understand the actual competitive terrain, is our leadership and judgment sound enough to execute this well, and can our operation actually sustain what we’re about to commit to. Skipping straight past that isn’t confidence. It’s a plan built without having checked whether the ground underneath it can hold it.

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