Wizard of Ads Monday Morning Memo

Is Your Planning Gestalt or Structural?


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Michael Dell and Shaquille O’Neal planned their work and worked their plans.

Dell understood the formulas, and followed the rules, of efficiency.

O’Neal understood the formulas and followed the rules of basketball.

Each of them faithfully followed a Structural plan.

Michael Dell invented nothing, improvised nothing, and innovated only once. But that single innovation made him a billionaire. Dell’s innovation was to bring tested, reliable, proven methods of cost-cutting to the manufacturing and distribution of computers. When all his competitors were selling through retailers, Dell sold direct to consumer. This made his costs lower and his profits higher.

Michael Dell’s strengths are discipline, professionalism, and Structural thinking.

Likewise, Shaq says, “I didn’t invent basketball, but I am really good at executing the plays.” Discipline, professionalism, and Structural thinking made Shaq an extraordinary basketball player. These same characteristics also made him an amazing operator of fast-food franchises.

“The most Shaq ever made playing in the NBA was $29.5 million per year. Now, it’s estimated that the big man is bringing in roughly $60 million per year, much of which is coming from his portfolio of fast-food businesses around the U.S.”

– 24/7wallst.com

Shaq didn’t invent car washes or Five Guys Burgers and Fries, but he owns more than 150 of each.

Michael Dell and Shaquille O’Neal are masters of Structural planning and thinking.

Structural thinking relies on proven elements and best practices. “Gather the best pieces and processes and connect them together like LEGO blocks. What could possibly go wrong?”

Structural planning and thinking:

Invent, Improvise, Innovate?

“NO, because those things are untested. We want to avoid mistakes.”

Reliable, Tested, Proven?

“YES!”

Steve Jobs and Michael Jordon are masters of Gestalt planning and thinking.

Gestalt planning and thinking:

Invent, Improvise, Innovate?

“YES!“

Reliable, Tested, Proven?

“NO, because those things are predictable. We want to be different.“

The fundamental idea of Gestalt thinking is that the behavior of the whole is not determined by its individual elements; but rather that the behavior of the individual elements are determined by the intrinsic nature of the whole.

It is the goal of Gestalt thinking to determine the nature of the whole, the finished product.

Gestalt thinkers who can fund their experiments and survive their mistakes often become paradigm shifters and world-changers.

Steve Jobs got off to a slow start because he refused to use MS-DOS, the operating system that everyone else was using. But he was sensitive to the needs and hungers of the marketplace. When Steve Jobs had a crystal-clear vision of the things that people would purchase if those things existed, he brought those things into existence.

Structural thinkers rely on planning and execution. Gestalt thinkers rely on poise and flexibility, often deciding on small details at the last split-second. Ask a Gestalt thinker why they do this and most of them will tell you, “I decide at the last minute because that is when I have the most information.”

The reason you never knew what Michael Jordan was going to do is because Michael Jordan had not yet decided. Michael’s internal vision was simple and clear: “Put the basketball through the hoop.” With the clarity of that crystal vision shining brightly in his mind, Michael could figure out everything else along the way.

Gestalt thinkers like Steve Jobs and Michael Jordan always “begin with the end in mind.”

When a Gestalt thinker has a crystal-clear vision, they have everything they need need to create all the little bits and pieces that will be required to bring that vision into reality.

Gestalt thinkers cannot give you the details of their process in advance, because they have not yet invented the process. But when a Gestalt thinker has achieved the hard clarity of a crystal-sharp vision, they are often perceived as being an “uncompromising perfectionist.”

Steve Jobs, Brian Scudamore, Jeff Bezos, Elon Muskrat.

Good News: Structural Thinkers and Gestalt Thinkers are equally likely to become successful.

The bad news is that I don’t believe we get to choose which one we will be. I think that “details first” Structural people and “details last” Gestalt people are both born that way.

Structural and Gestalt need each other.

A Gestalt ad writer needs a Structural business owner to deliver what his Gestalt ads will promise. And a Structural business owner needs a Gestalt ad writer to envision a way for his products and services to be more highly desired than those of his competitors.

Separately, Structural and Gestalt will both struggle.

But together, they can take over the world.

That’s the money, right there.

Roy H. Williams

Talya Rotbart is shepherding our roving reporter and his deputy, Maxwell, this week in Cortina d’Ampezzo, Italy, that lovely city where the 2026 Winter Olympics will be held. The Rotbarts are being escorted by Maxwell’s sister, Avital, and her husband Ben, who live in vivacious Vicenza, Italy, just two hours away.


The roving Reporter and deputy Maxwell will return with a new episode of MondayMorningRadio on Monday, May 5th. – Aroo, Indy Beagle

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Wizard of Ads Monday Morning MemoBy Roy H. Williams

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