Creativity

Starting With A Diagram

Jon Kolko

May 8, 2023

5 minute read

A simple diagram can define a problem and set the stage for innovation.

Years ago, I was interviewing for a job at a startup called MyEdu. I was in a conference room talking with the main product leader, Frank Lyman, about the startup's goals. He got up and drew three circles on the whiteboard.

Frank labeled the first circle Academic. He described startup's already-developed free tools that help students with college. We talked through these tools that hundreds of thousands of students were using each day. Although the tools were massively successful, being free, they weren't generating any revenue for the company.

The second circle was labeled Employer. It represented the startup's tools for recruiters, who could sift through students to find attractive job candidates. That was to be the business model of the company—to help students get jobs.

In the middle of the third circle, which connected the other two, Frank wrote a big question mark. He explained that the startup lacked a way to help students persuade an employer to hire them, and that was the next step in the evolution of the company.

Over time, the question got an answer, something we called a “rich profile”—a tool like LinkedIn but designed specifically for college students.

Students didn't need to build their profile because the system would do it for them. The more they used our free academic tools, the richer their profile would become, and the more enticing the student would appear to recruiters. Ultimately, the development of this tool was the innovation that led directly to our acquisition. But at the time, it was just a sketch of an incomplete story, poorly drawn, on a whiteboard. It was what you might call a “stupid-simple” sketch.

Frank later taught me a basic principle that I remember and teach my students. He called it “simplicity on the other side of complexity.” Here's how he explained it.

Draw a basic bell curve. From left to right is understanding, and up and down is complexity. At the left of the diagram, the beginning of taking on a complex problem, you are blissfully naïve. Your descriptions are overly simplistic and reductive. They are based on assumptions stacked on top of guesses, so they are likely wrong and incomplete. Because you don't know what you don't know, your arguments sound poorly thought out, and hard to believe.

As you start to experience more and more, gaining knowledge and insight, you move toward the right of the diagram. You see things from different perspectives, and you start to form an integrative picture of the problem space. At the midpoint—the peak—of the curve, you're seeing the meaning in the data and forming an opinion about it. This means that, to some extent, you own the information—it's meaningful to you, so you can act on it.

You can't necessarily communicate that information, though. You've integrated it for yourself, but that doesn't mean you've distilled it to a meaningful, concise story for someone who's still at the left of the curve. But it's at the midpoint in the curve that people typically try to explain complex ideas. Because they have all of the data, they think other people need all of the data, so they distribute a massive document or spreadsheet or orate an endless meeting. They describe everything they know, and everything they know is overwhelming. The audience often leaves more confused than they started.

Avoid inflicting information overload by continuing to experience things, find that meaning in the data, and revise and recast your opinion. As you do, you'll move beyond the midpoint toward the far right on the curve where informed simplicity lives. It's where you'll be able to not only synthesize the content into your worldview, but also discern the idea's essence in a way that you can communicate to other people. And you'll be able to communicate it so simply and directly that you can also move people with little or no knowledge of the content to the right of the curve.

The place you land on the right—the simplicity on the other side of complexity—is often obvious in retrospect. That's sort of the point: You've made it obvious to others because you did the heavy lifting of getting through the mess.

Frank borrowed the idea from Oliver Wendell Holmes, the Supreme Court justice who said:

“For the simplicity that lies this side of complexity, I would not give a fig, but for the simplicity that lies on the other side of complexity, I would give my life.”

Frank's three-circle diagram was simplicity on the other side of complexity. He had been living with an academic suite of products for close to a year, making no money but accumulating tons of users. He had no business model around those products, but over time—through trial, error, conversation, and meaningful reflection, Frank had worked his way towards a simple framework that represented the direction of the entire company.

When, later, I found myself noodling on the diagram, I realized that in its simplicity was power. Frank had transferred complex ideas to me in such a simple container. As I drew the diagram, I gained ownership over the knowledge and the problem itself. I realized I actually had a pretty good understanding of the business goal, and I could start to imagine the product suite that would get there.

More important, I saw the opportunity that Frank saw. His diagram provoked meaning for me because its simplicity was a placeholder for a large, important, and well-considered vision. Frank hadn't solved the problem; he had synthesized it into a strong, simple, powerful frame.