On the Risk of Making Every Judgment With Your Own Eyes Alone — Trust Only Your Own Sight, and the Organization Closes Its Eyes
The third post in Part Two of The Startup Prince. A founder's judgment is the asset that carried the company this far — but the moment it becomes the only standard for every decision, it shuts the organization's eyes. We look at why Machiavelli made the choice of ministers the first measure of a ruler's ability.
The previous post was about moving an organization through understanding rather than orders — handing over context, sharing the standards of judgment, getting people to move even where the founder isn’t watching. But there’s a next gate that founders who make it this far often trip over. They share context diligently, and yet every decision is still made with their own eyes alone.
A founder’s judgment is an asset. The company exists because they saw an opportunity nobody else did, and it got this far because at countless forks their call was the right one. The trouble is that this very record of success breeds a dangerous conviction: “In the end, my judgment turns out to be the most accurate.” The moment that sentence becomes the only standard inside the organization, the company can no longer grow beyond the size of one person’s field of vision.
The Company Where Every Decision Passes Through One Person
The symptom usually shows up as intervention. What the person responsible decided, the founder overturns. The final pick among design drafts, the last word on a hire, even the wording of a single line — everything ends up passing through the founder’s hands. And the founder reads this as diligence. They’re accountable for everything in the company, so of course they do it.
But here’s what happens in an organization when this repeats. Instead of making their own calls, people gradually start guessing at what the founder would think. Rather than using their expertise to build the best proposal, they build the proposal that will clear the founder’s taste. In meetings, they watch the founder’s face instead of voicing an opinion. On the surface the organization looks quiet and efficient. In reality, everyone has closed their eyes, and only the founder’s are open.
The most painful part is that the people the founder hired usually know their field better than the founder does. The company pays dearly to bring in experts, then overwrites that expertise with its own judgment at precisely the moments it was meant to be used. The company could have had ten pairs of eyes. It still runs on one.
How Machiavelli Sizes Up a Ruler by His Ministers
In The Prince, Machiavelli takes the first measure of a ruler’s ability to be who he has chosen to keep around him. If the ministers are capable and loyal, the ruler can be judged wise, because he recognized their ability and kept it intact. If the people around him are incompetent, the verdict is already in — that choice was itself the first blunder.
What deserves attention is his division of minds into three kinds: the mind that understands on its own, the mind that recognizes what others have understood, and the mind that understands neither by itself nor through others. The first, he says, is excellent; the second, good; the third, useless. The point worth holding onto is that the second belongs to the category of excellence, not incompetence. Even if you cannot see through everything alone, if you can recognize when someone else has seen correctly and adopt it, you are a capable ruler.
The question this puts to a founder is this. In straining to be the first kind of mind, am I closing off even the chance to exercise the second? The compulsion to see everything best oneself often makes it impossible to recognize when someone else has seen better.
Judgment Is an Asset — and a Liability When It’s the Only Standard
Let’s avoid a misreading. None of this means the founder should set judgment down and put everything to a vote. The company’s direction, what it will refuse to do, where it will place its bets — those remain the founder’s to decide. Just as a company that leans on borrowed strength is precarious (post 3), a company whose founder has abandoned their own judgment loses its heading.
The distinction to draw is not about the authority to decide but the material the decision is made from. What’s dangerous is not that the founder decides; it’s that the decision is assembled only from material their own eyes gathered. A company where the founder’s judgment is the sole input knows only what the founder knows and looks only where the founder looks. On the day the founder is wrong, there is not a single mechanism inside the organization to catch it.
And conviction hardens with time. If the founder’s calls keep getting adopted and the outcomes aren’t bad, that looks like proof the founder was right. But if no other judgment was ever tried in the first place, that record is not evidence that the founder’s eye was correct — only a record that no other eye ever got a turn.
Opening a Second Pair of Eyes
The method isn’t grand. It starts with not saying your own judgment first. The moment the founder leads with a conclusion, the discussion narrows into a review of the founder’s proposal. Hear the responsible person’s proposal first, ask why they judged that way, and then weigh whether their reasoning beats yours.
Separating reversible decisions from irreversible ones helps too. If a thing can be undone, it’s better to let the responsible person’s call stand even when it differs from yours. If an organization never accumulates the experience of deciding by its own judgment and then seeing the result, the number of people who can actually judge will never grow. The decisions where the founder’s eye absolutely must prevail are fewer than you’d think.
Above all, what’s required is not fearing the experience of finding your own judgment wrong. Show one flash of discomfort in a room where your proposal lost, and the organization reads it exactly and closes its eyes again. Conversely, let people see the founder say once, “that call is better than mine,” and from then on they begin looking with their own eyes. In Machiavelli’s terms, that is the moment the second kind of mind — the ability to recognize when another has seen correctly — starts working inside the organization.
The question to check yourself against is simple. Over the past month, how many decisions went the way a team member judged rather than the way you did? If nothing comes to mind, the organization has its eyes closed right now.
The next post takes on the other face of this problem. However hard a founder tries to borrow other people’s eyes, what if the information reaching them has already been filtered and smoothed? It’s about the organization where bad news never makes it across the founder’s threshold.