The Law of Role-Playing (See Through People’s Masks)

This is the third post in my series on applying mental models from Robert Greene’s The Laws of Human Nature to the real, messy world of building a business. I’ve already covered Irrationality and Narcissism.

Today, I am moving to Chapter 3 — The Law of Role-Playing.

Greene’s insight is sharp and practical: everyone wears a mask. You see it in the polite smile, the reassuring “everything is fine,” even when it’s not. People rarely voice their true doubts or objections, but they almost always reveal them through subtle “leaks” — their tone, gestures, or disengagement.

When we sense we’re losing someone’s confidence, our instinct is to try harder to win them over. But in business, that isn’t always possible or wise. It’s often better to build a system that protects you from the chaos their unspoken emotions might create later.

I learned this lesson in 2013, right after my MBA. I was working with an architect friend, and we pitched to a client looking to renovate his home. After several discussions, my friend and his team delivered a detailed presentation to the client and his wife.

The husband was thrilled, nodding with excitement and praising the design. His wife, however, told a different story. She smiled politely and said, “It’s lovely,” but spent most of the meeting on her phone, calling for their child, completely disengaged.

In that moment, I realized the truth: while the husband was sold, the wife, the other key person who would live with the result — wasn’t. I could already see what would follow: constant changes, delays, frustration, and financial loss once the project began.

So instead of trying to convince her, I decided to build protection into our engagement. It was a simple system, a structure designed to safeguard us from the emotional chaos we could see coming. After discussing it with my friend, we adopted a three-step approach used across such projects.

• First, the Freeze Email. We sent the final design brief and wrote, “Please confirm the design brief. Any future changes will be charged extra.” The couple made a few minor edits and approved it.
• Second, the Risk-Shift Contract. We recommended that the client hire the contractor directly. Our scope was limited to design, with an optional project management fee if they wanted us involved during execution. This ensured that any construction-related disputes wouldn’t fall on us.
• Third, the Front-Loaded Payment. We structured our design fee so that 90% was paid before final delivery. The remaining 10% was treated as a buffer, essentially the amount we were ready to lose if things went south.

Two weeks after work began, everything unfolded exactly as expected. The wife began requesting changes almost daily, driving the contractor to quit within two months. Soon after, the clients started calling us for redesigns and to help onboard a new contractor.

Luckily, we were protected. Our work was complete, our engagement terms were clear, and ninety percent of our payment was already in the bank.

We never got our final 10% payment and later heard that the 3 months long work took over a year to be completed at 5X our initial estimate.

That experience reinforced a powerful truth from Greene’s law. It’s not enough to read people, you must design systems that act on what you see. Observing human behavior matters only when it translates into structure, clarity, and protection.

See the real person behind the performance. Then, build a system strong enough to handle them.