Source: I'm a trained sailor.
Engineers below the upper senior levels typically operate with an "infinite" mindset in making these choices. We all laugh at the relevant XKCD[0] because there's a grain of truth in there. This isn't a knock on engineering, it's just the nature of operating at the lowest levels. You become involved in the problem and you solve for local maxima.
Leadership done well is going to offering transparency to the people on the ground level, communicating timelines and strategy in a way that is relevant to the problem at hand, so people know, for example, how long they can spend solving a particular problem.
Where this sometimes goes wrong is, the higher you go in leadership, the lesser certainty there is. There are no "right" answers, there isn't perfect information, and yet, decisions must be made. If engineering is operating on different base assumptions, those decisions will look wrong (and they might be). And yet, someone needs to get people aligned and moving forward, because moving fast in the wrong direction is typically better than moving too slow, even in the right direction.