On the Risk of Dominating Instead of Leading — Obedience Reaches Only as Far as the Order; Understanding Goes Beyond It
The second post in Part Two of The Startup Prince. Extracting obedience through the power of the office is not the same as leading people. We look at why an organization that runs on compelled obedience alone moves only while the founder is watching, borrowing Machiavelli's distinction between two kinds of power.
The previous post was about choosing a battlefield you can win. Once you’ve chosen it, the next question is how to get people to move on it. And here a leader falls into one of the most common illusions there is: treating getting people to move and leading people as the same thing.
The office of the founder comes with power. The authority to set salaries and reviews, to decide who is hired and fired, to make the final call. Use that power and getting people to move isn’t hard. Give an order and it usually gets done. The trouble is that what you’ve extracted that way is not leadership but obedience.
The Organization That Moves Only While the Founder Is Watching
An organization run by domination has clear symptoms. When the founder isn’t in the meeting, decisions stall. Even trivial matters travel upward on the words “we’ll have to ask the founder.” During the few days the founder is away, the organization defers its judgment until they return rather than starting anything new. On the surface the founder’s authority looks unshakable, but in reality the entire organization is confined inside the processing capacity of one person.
An organization like this does the work it’s told to do well. It’s just that in the face of work it wasn’t told to do — the unexpected situation, the problem the founder never anticipated — it comes to a halt. Obedience only functions as far as the order reaches. What lies beyond it — moving in the right direction on your own when no one has told you to — is never produced by obedience.
Power Built by Force and Power Built by Support
In The Prince, Machiavelli distinguishes two paths to power. One is to rise by borrowing the strength of the powerful few or through force; the other is to rise by winning the support of the people. He saw the stability of the two as sharply different. A ruler raised by a powerful few stands as their equal, is therefore always kept in check, and collapses when adversity strikes if the people’s goodwill isn’t there. A ruler standing on the people’s support, by contrast, he judged to have a solid foundation.
The point is where the source of the power lies. Power built by force holds only while that force is still being applied. The moment the force stops — the moment the ruler steps away or their strength weakens — the power wavers with it. Power built on support, because people follow of their own accord, holds even when the ruler doesn’t compel them one by one. It’s the same logic as the fortune of the previous post: when the source of strength lies outside, it collapses when those conditions vanish; when it lies within, it lasts.
Obedience Reaches Only as Far as the Order; Understanding Goes Beyond It
Translated to an organization, it goes like this. Obedience won through the power of the office functions only within the range that power reaches — as far as the founder’s eyes fall, the items the founder specified, the metrics that show up in reviews. The moment it crosses that boundary — a situation no one is watching, a problem not in the rulebook, a point where the instruction and reality diverge — obedience loses its force. Work that wasn’t ordered goes undone, and where judgment is called for, judgment gets deferred.
Understanding works differently. If a member genuinely understands what we are doing and why, they move in the right direction even where there’s no instruction. Meeting an unforeseen problem, they reason out for themselves how the founder would have judged it and decide accordingly. This is what fills the beyond that obedience can’t reach. Machiavelli also said that ruling through fear can be the safer course — but fear only makes people pull back from a particular action; it doesn’t manufacture initiative where there was none. Fear is useful for preventing what shouldn’t be done, but making someone do a good thing no one ordered takes understanding.
Why Domination Is Easier
And yet many founders lean toward domination. The reason is simple: domination is faster and easier. Explaining why a task has to be done this way, sharing the criteria for judgment, and waiting until a member has absorbed it is slow and takes effort. Saying “just do it this way,” by contrast, produces an immediate result. In an early-stage startup where every day is urgent, that difference in speed is enormously tempting.
The problem is that the bill for that convenience arrives later. An organization that has run on instruction alone grows larger while the number of people who can actually judge stays at one — the founder. If the organization has reached a hundred people but a hundred people’s worth of judgment all has to pass through a single person, that person is the bottleneck. The effort spared on planting understanding early comes back, once the organization has grown, as a ceiling on how far it can scale.
The Work of Planting Understanding
Leading isn’t cutting back on instructions and leaving people to fend for themselves. It’s conveying context alongside the instruction instead of the instruction alone. When you pass along not just what to do but why it matters and by what criteria to judge it, a member gains the raw material to decide for themselves the next time a similar situation arises. Treating a decision made while the founder was away — even one whose outcome was disappointing — not as something to punish outright but as a chance to sharpen the criteria of judgment is the same work. Punish an act of independent judgment once, and the organization goes right back to waiting to be told.
This isn’t the founder giving up power; it’s moving the source of that power from outside the office into the organization itself. An organization that moves only under compulsion stops the moment the founder stops compelling it, while an organization that moves through understanding moves even when the founder isn’t watching. To borrow Machiavelli’s terms, it is power standing on its own foundation rather than power standing on borrowed strength.
The next post takes up the risk of that understanding flowing in one direction only. The founder has come as far as handing context to members — but still insists on making every judgment through their own eyes alone. It’s about how, the moment a leader overtrusts their own eye, the organization’s eyes fall shut.