To further agree with what you are saying...
In many sports: people put work in to run their OODA loop faster even they don't call it that. People watch videos of their opponents to learn how to more quickly orient their opponents actions with the context of the sport.
In engineering: unittests, debuggers and IDEs are all designed to provide information that allows a faster OODA loop.
The idea of rapid iteration is based on the idea in exploratory settings with low information a faster OODA loop is often better than a smarter but slower OODA loop.
It was pretty awesome hearing my son's team making this type of observation on the field as the opposition repeated the same offensive play, and adapt their response.
This is insightful. Each node in the chain is a self-correcting loop. The trick is to make sure that information is sent up the chain more rapidly so that each node can use it to act on its own within the broader objective. Note that "information loss" is a function of both the number of nodes in the chain and time.
[1] https://erikbern.com/2019/10/16/buffet-lines-are-terrible.ht...
I don't think that's necessarily true. Information going up the chain of command will always be a bit outdated, distorted, and incomplete (unless you can just live-stream video with sound to your command center). So with properly trained soldiers decisions made at lower level can actually be better than those made by higher-ups.
In the context of the military, there are ways of reorganizing your command structure to enable faster OODA loop cycling. For example, a major driver of the "slowness" of traditional armies is their centralization of command. Propagating new intel up the chain and orders down to the troops takes a lot of time, especially when intermediate nodes keep dropping out. If you can delegate your decision making to the lowest possible level, this will make the average decision slightly worse, but because you can make each decision much faster you can still come out ahead overall. This is one of the ways an organization can "practice" the loop. (And coincidentally, one that growing startups often struggle with since it is very difficult to transition from direct command to delegation based command)
I also don't agree with your claim that you can't "practice" the loop on an individual level. Anyone who suffers from indecision in the face of uncertainty and overwhelming options ("analysis paralysis") should know that it is something you get better at over time, especially when you need to be doing it under time pressure.
Source: Was a Navy officer for 14 years, we had tons of discussions of "how to get into the opponents loop" during briefings and trainings. Note that in the military it is sometimes possible to actively slow down the opponents OODA looping, something that is probably illegal for most civilian companies. (Though see https://www.joelonsoftware.com/2002/01/06/fire-and-motion/ for a legal example)