I think this is not a good explanation. “Get on the hill” is a bad order. “We want to get on that hill to gain fire control on that road” is much better. Because that means the on the ground troops can achieve the objective through an entirely different means if the hill is not viable.
Critically, and this is why military analogies don’t work with most large orgs, the on the ground folks don’t need to confirm with top leadership that an alternative tactic is sufficient. In messy business orgs, middle managers play it way too conservatively and try to get their bosses to green light every decision by presenting them a synthesized and watered down view (“the hill is well defended, the other hill is better”). But this is slower, error prone, and at risk of compromise to minor communication failures because the condensed time and attention for the synthesized logic won’t capture the full reasoning (“I don’t get why the second hill is better. Just do the first one”).
You're right on expanding get on the hill. I didn't want to get too much in the weeds, but thank you for explaining it better.
I would push back a bit on your second point and say that there are many decisions around tactics made in business that are not confirmed with higher ups. This is why your expanded first point is so important. People at all levels of the org are making decisions all the time and you want them to have the most complete picture possible when doing so.
Critically, and this is why military analogies don’t work with most large orgs, the on the ground folks don’t need to confirm with top leadership that an alternative tactic is sufficient. In messy business orgs, middle managers play it way too conservatively and try to get their bosses to green light every decision by presenting them a synthesized and watered down view (“the hill is well defended, the other hill is better”). But this is slower, error prone, and at risk of compromise to minor communication failures because the condensed time and attention for the synthesized logic won’t capture the full reasoning (“I don’t get why the second hill is better. Just do the first one”).