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I don't trust that CTOs are trained for situations where retreat isn't an option.

Executives can always quit or declare bankruptcy if they screw up a company. Can't do that when you screw up a country.

Lol, pretty sure you can. See Afghanistan withdrawal, Iraq, Vietnam etc etc

Resigning as a bad government is a thing you can do.

In the middle of a conflict?

That is usually the end of the conflict.