Rosencrantz and Guildenstern Are Dead (But Your CRO and SEO Strategy Shouldn't Be)

One of my literary heroes, Tom Stoppard, passed away recently. His work has thrilled me since my introduction to Rosencrantz and Gildenstern at fourteen, and then Arcadia in my early twenties. A person who can weave romantic literature, the second law of thermodynamics and the school of English landscape design, all into the wild romp that is Arcadia, is forever my hero.

Then last week I found myself in a Slack thread with the team from One of One Brands (who I believe to be one of the best brand strategy, design and stewardship teams in the business) where we somehow managed to philosophically evolve "no custom development but fully custom design", into an extended meditation/mediation on tautology. It happens.

This is exactly the kind of conversation that makes me think, and this blog is all about stuff that makes me think.

So here I am: re-reading Stoppard, debating impossible design specifications, and suddenly I'm seeing tautological pairs everywhere I look in ecommerce.

Stoppard spent his entire career writing about people who exist entirely in relationship to each other. His characters don't just complement each other, they define each other. Remove one and the other ceases to make sense. They're locked in interdependent systems whether they like it or not, which Stoppard found both hilarious and tragic. (Though if we're being honest, The 15-Minute Hamlet is possibly my favorite play ever, both to read and to perform. Stoppard understood that sometimes the best way to reveal tautology is to speed it up until it becomes absurd.)

Which brings me to ecommerce, where I keep watching teams fight battles that Stoppard already explained were unwinnable.

There's a certain kind of ecommerce meeting I've sat through too many times. The SEO team wants to add more content to category pages. The CRO team wants to remove content to reduce friction. SEO wants longer product descriptions for keyword density. CRO wants shorter ones for scannability. The two teams present their cases, backed by data, glaring at each other across the conference table like they're locked in mortal combat.

They're not opponents. They're Rosencrantz and Guildenstern, Vladimir and Estragon, Harry Potter and Voldemort. They're tautological pairs: defined entirely by their relationship to each other, unable to exist independently, locked in a dance that looks like conflict but is actually codependence.

The sooner you accept this, the sooner you stop wasting time trying to "win" arguments that have no winner.

The Tautology Problem (Or: Why Vladimir Needs Estragon)

In Samuel Beckett's Waiting for Godot, Vladimir and Estragon spend two acts waiting for someone who never arrives, bickering about whose fault it is that they're still waiting. They threaten to leave each other. They insult each other. They're utterly miserable together.

They never actually leave. Because neither one has any meaning without the other. They're not two separate people who happen to be friends. They're a tautological pair: Vladimir exists to wait with Estragon, Estragon exists to wait with Vladimir. The waiting defines them both. Remove one, and the other ceases to make sense.

Your ecommerce teams are doing the same thing. Design wants beautiful, minimal interfaces. Development wants maintainable, scalable code. They present these as conflicting goals, as if one must be sacrificed for the other. But beautiful interfaces that can't be maintained collapse into technical debt. Maintainable code that produces ugly interfaces drives customers away. You can't have one without the other, not if you want something that actually works.

SEO and CRO are the same. You can't optimize conversion rates on traffic you don't have. You can't benefit from traffic if it bounces immediately. The two disciplines define each other: SEO exists to bring people who CRO can convert, CRO exists to convert people that SEO brings. Treating them as separate functions is like trying to stage Waiting for Godot with only Vladimir.

The play doesn't work. Neither does your strategy.

Rosencrantz and Guildenstern Are Dead (And So Is Your Org Chart)

In Stoppard's masterpiece, Rosencrantz and Guildenstern are minor characters from Hamlet elevated to protagonists. They spend the entire play trying to figure out what's happening, what their role is, whether they have any agency at all. They're interchangeable (even Stoppard couldn't consistently remember which was which, which was rather the point). They're defined entirely by their relationship to Hamlet and to each other.

And in the end, they die offstage, killed by a plot they never understood.

The brilliance of the play is that Stoppard shows us two characters who think they're making independent choices, who think they have separate identities and goals, but who are actually just two faces of the same function in someone else's story. They can't escape their tautological relationship. They can't individuate. The harder they try to assert independence, the more obvious it becomes that they only exist in relation to each other.

Your ecommerce org chart has Rosencrantz and Guildenstern too. They're usually called "Marketing" and "Product," or "Creative" and "Tech," or "Brand" and "Performance."

They attend the same meetings. They work on the same projects. They have completely different OKRs and completely different success metrics and absolutely no shared understanding of what they're trying to accomplish together.

One team optimizes for brand consistency. The other optimizes for conversion. These aren't opposing goals, they're tautologically linked: brand consistency that kills conversion destroys the brand, conversion tactics that undermine brand trust kill conversion. But because they're measured separately, managed separately, rewarded separately, they fight each other like they're enemies instead of recognizing they're two sides of the same coin.

The tragedy isn't that they disagree. The tragedy is that they think they're having separate conversations when they're actually in the same play, just like Rosencrantz and Guildenstern. And like Rosencrantz and Guildenstern, they'll die offstage, killed by forces they never understood, wondering what went wrong.

Harry Potter and Voldemort (Or: The One Cannot Live While The Other Survives)

The prophecy in Harry Potter says "neither can live while the other survives." Harry and Voldemort are locked in a tautological relationship: Voldemort exists to be Harry's nemesis, Harry exists to defeat Voldemort. Neither one has meaning without the other.

(Yes, I'm citing Harry Potter. This is a tactical choice. If I'm going to tell you that your entire organizational structure is predicated on a fundamental misunderstanding of tautological relationships, I need at least one reference that softens the blow for people who have not yet been thrilled by Stoppard, Beckett or even Ionesco.)

This is design and development in ecommerce.

Design wants pixel-perfect interfaces. Development wants to ship quickly. They present this as a tradeoff: you can have it beautiful or you can have it fast, pick one. But beautiful designs that take six months to implement miss market opportunities. Fast implementations that look terrible drive customers away. The real question isn't "design or development," it's "how do we make these tautologically linked functions work together instead of against each other?"

The answer, as with most tautological pairs, is to stop treating them as separate variables to be optimized independently and start treating them as a system.

In macroeconomics, this is why the Phillips Curve exists: it describes the relationship between inflation and unemployment. For decades, economists thought you could pick a point on the curve, trade off a little more inflation for a little less unemployment, or vice versa. Then the 1970s happened, and we learned that the curve itself shifts based on expectations, that you can't optimize one variable while holding the other constant, that the system is more complex than a simple tradeoff.

Ecommerce is the same. You can't optimize CRO while holding SEO constant. You can't improve user experience while freezing development capacity. You can't reduce site speed while maintaining conversion rates. The variables are linked, and when you try to optimize one in isolation, the whole system shifts under you.

The Coordination Problem (Or: Why Godot Never Shows Up)

Here's the thing about Waiting for Godot: Godot never shows up. Vladimir and Estragon wait through two entire acts, having the same conversations, making the same plans, threatening the same departures. The play ends exactly where it began, except now they've wasted two acts worth of time.

The play is about the futility of waiting for external salvation when the problem is internal coordination. Vladimir and Estragon don't need Godot. They need to figure out how to exist together without making each other miserable. But they can't, because they're locked in patterns they can't see past, waiting for someone else to solve a problem only they can solve.

Your ecommerce teams are waiting for Godot too. SEO is waiting for CRO to stop ruining their rankings. CRO is waiting for SEO to stop prioritizing keywords over conversion. Design is waiting for Development to care about aesthetics. Development is waiting for Design to care about feasibility. Everyone is waiting for someone else to change, to compromise, to finally understand.

Godot never shows up. The coordination problem doesn't solve itself.

Your teams are trying to optimize the same business. SEO brings traffic. CRO converts it. Design makes it beautiful. Development makes it functional. Customer service keeps people happy. Finance makes sure it's profitable. These aren't separate businesses, they're separate functions trying to optimize the same system.

When they work at cross purposes (SEO stuffing keywords that CRO says reduce conversion, CRO pushing pop-ups that SEO says hurt rankings, Design creating interfaces that Development can't maintain, Development building features that Design says are ugly), they cancel each other out. You get Vladimir and Estragon, having the same argument they had yesterday, waiting for something to change.

How to Stop Waiting and Start Coordinating

Both Stoppard's and Beckett's characters are tragic because they can't escape their tautological relationships. They're stuck in their plays, locked in their patterns, unable to see that the conflict is built into the structure.

Your ecommerce teams aren't stuck in a play. You can actually change the structure. You just have to stop pretending that SEO and CRO are separate optimization problems, that Design and Development are opposing forces, that Brand and Performance can succeed independently.

Here's what that looks like in practice:

SEO and CRO sit in the same room and define success together. Not "SEO success" and "CRO success." Success. Which probably looks like "qualified traffic that converts" rather than "maximum traffic" or "maximum conversion rate." When you measure them as a system instead of as competing functions, the tradeoffs become obvious: yes, the pop-up hurts SEO rankings, but does it hurt qualified traffic? Yes, the long product descriptions help keyword density, but do they help conversions? You can't answer these questions separately.

Design and Development plan together from the beginning. Not "design throws it over the wall and development figures out how to build it." Both disciplines in the room, talking about what's feasible and what's important and where the constraints are. Beautiful interfaces that can't be maintained aren't beautiful. Maintainable code that produces ugly interfaces isn't maintainable (because no one will want to keep using it). Vladimir needs Estragon. Design needs Development. Stop pretending otherwise.

Brand and Performance acknowledge they're Harry and Voldemort. Neither can live while the other survives, but also, neither can survive without the other. Brand builds the trust that performance monetizes. Performance generates the revenue that funds brand building. You can't optimize one while destroying the other. You have to optimize the system.

This is not a call for consensus or compromise. Vladimir and Estragon don't need to agree on everything. They just need to recognize that they're in the same play, that their fates are linked, that optimizing their individual positions while ignoring each other is futile.

Rosencrantz and Guildenstern don't need to understand Hamlet's entire plot. They just need to stop acting like they're in separate plots, stop waiting for someone else to tell them what to do, and start coordinating with the reality they're actually in.

The Uncomfortable Truth About Tautology

Tautological relationships are uncomfortable because they resist simple optimization. You can't just "maximize X" when X is tautologically linked to Y. You have to optimize the system, which is harder and messier and requires coordination.

Stoppard understood this. His plays are full of characters who think they're independent agents making independent choices, only to discover they're defined entirely by their relationships to each other. The tragedy isn't that they're dependent. The tragedy is that they don't realize it until it's too late.

Your ecommerce teams don't have to be tragic. You can recognize the tautological relationships before you waste years fighting them. SEO and CRO are Vladimir and Estragon. Design and Development are Rosencrantz and Guildenstern. Brand and Performance are Harry and Voldemort.

The teams fighting about this aren't wrong to care about their metrics. They're wrong to think their metrics are independent variables. They're wrong to wait for someone else to solve a coordination problem that only they can solve.

The question isn't how to win the fight. The question is how to recognize you're in the same play and start acting like it.

Stop waiting for Godot. Start coordinating.

Tom Stoppard spent decades showing us that the most profound conflicts aren't between opposing forces, they're between interdependent forces that refuse to acknowledge their interdependence. Ecommerce is still learning this lesson.

Don't die offstage, killed by a plot you never understood. Figure out which play you're in, recognize your tautological pairs, and start optimizing the system instead of the parts.