Essay · April 2026

When they want A and you want B

Curiosity as an operator move.

You walk into a meeting; they want one thing and you want another. Two paths from here.

The first path is easy: decide they are wrong, or shortsighted, or missing the obvious. Make your case louder, show your logic harder, assume they will come around if you explain it well enough. This path is expensive; it costs you the rest of the meeting, the quality of the decision, and usually the relationship.

The second path starts from a harder assumption: they are not crazy. Whatever position they are defending, it is sitting on top of an iceberg you cannot see: their knowledge, their experience, their constraints, their view of what went wrong the last time you tried something like this. Ninety percent of it is below the surface. The same is true of your own position; they cannot see what is holding yours up.

McKinsey's long-running research on organizational transformations finds that fewer than a third of them deliver on their objectives; the execution layer is the most common point of failure, more than strategy or talent. Kaplan and Norton's research on strategic execution found that ninety-five percent of employees in the companies they studied could not articulate their own organization's strategy. The gap between what a leader believes was decided and what the rest of the organization understood they should do is not a rare event. In complex organizations, it is the default.

The move is curiosity, not argument. The four magic questions do most of the work.

Help me understand. Opens them up; signals you are trying to see what they see, not prepare your counter. People share context when they feel curiosity behind the question, not a trap.

Why not? Surfaces the assumption. When someone shuts down an option, there is always a reason; it may be a real constraint, or it may be a leftover from something that happened in a previous role five years ago. Until you ask, you cannot tell the difference.

What if? Creates space for alternatives without forcing anyone to concede. Hypotheticals are cheap; they let both sides explore a third option without losing face on the first two.

What would it take to? Turns an objection into a list. Sometimes the list is short and doable; sometimes it reveals the real blocker. Either way you have moved from position to mechanism.

You walk out of the meeting one of three ways. You changed your mind, because they had information you did not. They changed theirs, because you had information they did not. Or you both landed on option C, which neither of you walked in with but which is better than either of the things you brought.

All three are wins. The only losing outcome is the one where you spent an hour arguing positions and neither of you learned anything about the iceberg.

The close matters. At the end of any meeting that mattered, the person with the highest clarity is the one who plays it back: let me recap what we just agreed; I will do X by Tuesday, you will do Y by Thursday, checkpoint on Friday. Not because anyone asked. Because that is how you find out, in the same ten seconds, whether your understanding and theirs are actually the same.

If it is not the same, you find out now, not in two weeks. If it is the same, you walk out of the room with a plan, and everyone knows who is doing what. That is the discipline. The meeting itself is the cheap part.