The most useful question in any conversation is some version of, what makes that important to you? It sounds simple, and that is the point. It moves the talk from surface facts to the thing the other person actually cares about.
Most people never ask it. We hear a need, assume we understand it, and jump to our answer. The one question slows that down for a beat and almost always surfaces something you would have missed, the real reason behind the request.
It works everywhere. In a meeting it finds the decision that matters. In an interview it shows genuine curiosity. In a one on one it turns a status update into a real talk.
Wingman listens for the moments where that question would land and reminds you to ask it, so the habit sticks until it becomes yours.