2nd Base - Reach Product Market Fit

When AI Gave Me 500 Book Covers and My Designer Gave Me One

Master the art of syntropy in design by moving beyond AI-generated noise to human-crafted clarity. Learn to manage designers who create order and meaning from chaos.


Get monthly GTM frameworks in your inbox.

Three hours. Five hundred variations. That's what it took for AI to fail at designing the cover for my new book, Syntropy. Lighthouses, fiber optic cables, Morse code, even David stars and Christian symbols I never asked for. Pure chaos multiplying into more chaos.

Thirty minutes with Guilherme, my designer at Kalungi. Six options. Problem solved.

This experience crystallized something I've been observing for years about design, creativity, and what I call syntropy: the human ability to create order from chaos, meaning from noise, value from void. It's the core concept of my upcoming book, and ironically, the cover design process became the perfect demonstration of why syntropy matters.

The Three Levels of Design Excellence

Through managing designers across dozens of companies, I've identified three distinct levels where great design operates. Most designers plateau at level one. The exceptional ones reach level two. But level three? That's where syntropy happens.

Level One: Following the Rules

At the foundational level, professional designers master the basics. They choose appropriate colors, maintain visual consistency, follow brand guidelines. They understand spacing, typography, hierarchy. This is table stakes.

When I prompted AI for my book cover, it operated entirely at this level. It followed rules. It combined existing patterns. It checked boxes. The results looked professional but felt hollow. Like a technically perfect meal with no soul.

I've learned to spot level-one work immediately. It's safe. It's correct. It's forgettable. When managing designers at this level, you're essentially quality control. Is the logo breathing? Are the fonts consistent? Is the hierarchy clear?

If you want to develop your eye for this level, I recommend reading "Design for Non-Designers." It'll teach you the vocabulary to articulate what you're seeing and guide designers past basic execution errors.

Level Two: Breaking Rules with Purpose

The second level separates competent from compelling. Here, designers don't just follow rules. They break them strategically. They introduce tension. They create moments of surprise. They make you slightly uncomfortable, then win you over.

This is where I've seen many managers stumble. They want immediate comfort. They reject designs that challenge them. But here's what I've learned: designs that feel perfect on first viewing rarely last. The ones that become iconic? They often feel wrong initially, then grow on you, then become indispensable.

When Linda suggested the bitmap effect for my cover, she was operating at level two. It wasn't the obvious choice. It introduced grain and imperfection into something that could have been smooth. But that imperfection told the story better than perfection ever could.

Managing at this level requires courage. You have to tolerate discomfort. You have to trust the designer's instinct even when your immediate reaction is resistance. You have to remember that your first impression is often wrong.

Level Three: Creating Syntropy

The third level transcends aesthetics entirely. It's where design becomes strategy, where every choice serves a singular purpose, where complexity transforms into clarity.

Guillerm reached this level when he asked, "What do you think about the idea of the book?" He wasn't asking about color preferences or font choices. He was building a mental model of the deeper purpose. When he said, "I was thinking about convergence," he'd extracted a theme I hadn't even articulated.

This is syntropy in action. Not adding more options, but finding the pattern hidden in the chaos. Not following rules or breaking them, but transcending them entirely to serve the core purpose.

At this level, the conversation shifts from "make it pop" to "what must this achieve?" The designer becomes a strategic partner, not a service provider. The work becomes about subtraction, not addition. Every element either serves the core purpose or gets cut.

The Syntropy Test

Here's how I now evaluate design work through the syntropy lens:

First, does it create order from chaos, or does it add to the noise? Five hundred AI variations added noise. Six thoughtful options created clarity.

Second, does it demonstrate understanding or just execution? When I asked AI for "human touch," it gave me fingerprints. When Guilherme heard "human touch," he understood warmth, personality, imperfection.

Third, does it make the next decision easier or harder? Each AI iteration made choosing more difficult. Guilherme's work made every subsequent decision obvious.

Managing Designers in the Age of AI

The traditional model of design management is dying. AI can handle level one. It's getting better at level two. But level three? That requires something AI cannot provide: the ability to extract meaning from context, to understand what's not being said, to create order that didn't exist before.

Here's what I've learned about managing designers who can create syntropy:

Stop asking for more options. Start asking for deeper understanding. The designer who shows you three thoughtful directions beats the one who shows you thirty variations.

Stop evaluating first impressions. Start living with designs for days before deciding. I've approved too many safe designs that felt good immediately and rejected too many great ones that challenged me initially.

Stop managing tasks. Start managing understanding. The brief isn't the job. Understanding the job is the job. When designers truly understand the purpose, the execution often manages itself.

The Conversation That Changed Everything

During that thirty-minute call with Guilherme, he revealed something profound. He'd had the same brainstorming session I'd had with AI: radio waves, signals, galaxies organizing into planets. But instead of generating hundreds of executions, he'd sat with the concepts until patterns emerged.

"It's really hard to come up with a visual solution," he said. Not because he lacked skills, but because he understood the complexity of what we were trying to communicate. AI never struggled. It just kept producing variations without understanding.

This is the difference between entropy and syntropy. Between noise and signal. Between AI and human creativity at its best.

Questions for Your Design Process

When did you last choose the designer who showed you the most options over the one who demonstrated the deepest understanding?

How many design decisions in your organization are made based on first impressions versus lived experience?

Which of your designers operates at level three, creating syntropy rather than variations?

What would change if you managed for understanding rather than output?

The Path Forward

Syntropy isn't just a concept for my book. It's the lens through which I now see all creative work. In a world where AI can generate infinite variations, the scarcest resource isn't creativity. It's the ability to create order from chaos, meaning from noise, clarity from confusion.

The designers who thrive won't be those who can produce the most options fastest. They'll be those who can look at chaos and see the convergence pattern hiding underneath. Who can extract principles from briefs. Who can create understanding, not just execution.

That's syntropy. That's level three. That's where your designers need to be.

The question isn't whether AI will change design. It's whether your designers will evolve from executing briefs to creating syntropy. The tools have changed. The levels remain. The choice is yours.


Check out my new book "Syntropy: How Humans Create Value in the Age of AI Entropy" for more frameworks on building exceptional marketing and product teams, explore T2D3.pro

Similar posts