Former U.S. ambassador to Israel Dan Shapiro on Thursday observed that President Donald Trump has an “instinct for ‘one and done’ “: a single, decisive strike to accomplish one’s aim and then move along. This makes sense in geopolitics. It aims to shock, reset the balance of power, and avoid prolonged entanglement. A single sharp move is meant to close a chapter.
The trouble starts when this mindset is brought into the world of business.
Business is not a one-off confrontation. It is a repeated game, played over time, with memory, reputation, and consequences that accumulate. In such an environment, “one and done” is rarely a sophisticated strategy. More often, it is an illusion of control – mistaking a decisive move for a final one.
Decisiveness matters in negotiations. Leaders are supposed to offer clarity, minimize uncertainty and move with confidence. A bold decision can spark a movement and establish leadership. But decisiveness is not the same as certainty. In business, almost no deal really signifies the end of the transaction. Markets respond, partners adapt, employees translate, and adversaries plan the next move. A judgment is enacted once, but its consequences are served up at the table over and over.
This is where the “one and done” mindset becomes risky.
Executives who are confident that they can secure a deal with just one aggressive play typically underestimate the system in which they are operating: Commercial relationships do not begin or end with any single deal, but rather develop over time. Supply chains are interdependent. Clients don’t forget how they’ve been treated. A staff also remembers how decisions were made. Competitors also learn from what they see. The field is not cleared after the move – it re-forms around it.
And that’s the thing about power in repeated games: it is not a function of how hard you push to close the deal; instead, any power you might have comes from sealing a good one. A contract signed under duress may crumple at the first stress test. A reorganization announced in the middle of the night may sound bold on a PowerPoint slide but flounder in implementation. A public ultimatum may win the day, but at the lonely price of weakening trust.
The irony, of course, is that leaders who try to exert control through “one and done” often find themselves with less of it. By declaring the interaction finished, they cease controlling the aftermath. By stating that it’s over, they refocus attention away from where the real action is taking place. And in business, it is the aftermath that really matters because it will determine whether value is preserved or eroded over time.
There isn’t much space for “one and done” in business, because the playing field can sour on you. Who you call on today may be the strategic partner, regulator, supplier or board member of tomorrow. Leverage shifts. Context changes. What feels like power in one quarter begin to feel like weakness in the next. The story of how a decision was made often matters more than the decision itself.
Strong negotiators understand this instinctively. They are not concerned with bringing the talks to a close; they are concerned with shaping the next stage. They’re not focused on closing statements, but future optionality. They wonder not just how anyone will sign a deal, but also how it will work when conditions change.
There are situations where speed and decisiveness are essential: ontaining a crisis, drawing a clear ethical line, or walking away from a partnership that no longer serves its purpose. But even in those moments, success is not determined by how forcefully the move is made, but by how well it holds once the moment has passed. Decisions that are clear but disconnected from what comes next rarely endure.
“One and done” may certainly sound strong, confident and like it comes from a place of leadership. But in business, where relationships repeat and power shifts, certainty is rarely final. More often, it is a temporary pause in a longer game: one that continues whether leaders acknowledge it or not.
