Taking risks to learn how to lead, fight, and win should be something our officers are encouraged to do:
Failure in training is vital in unconventional and conventional warfare environments. Battalion and higher staff must fail in training and then correct their mistakes. The battalion staff must complete the failure cycle-- failing and then adapting to prevent the failure in the future. Create mitigating mechanisms to reduce negative results -- in any exercise, without repercussion. Leaders must foster an environment that encourages honest mistakes.
One of the reasons I wanted to expand the number of divisions in the Army by integrating the Guard in a two-brigade division (with fire support for a three-brigade division) structure that provided a continuum of options from immediate deployment to mobilization to building new divisions (See "The Path of the Future Army") was the hope that by expanding the division command slots that the Army would combat the intense competition for those slots and thus reduce the zero-defects mentality that values lack of mistakes over all else in getting the jobs.
[The Army is brigade-based now with self-contained brigade combat teams, so my divisional organization is past the debate, but my concern about mistake aversion remains.]
Mistakes in COIN are more forgiving because the enemy can't exploit mistakes with the same speed or consequences as conventional enemies can exploit mistakes.
I'd rather have our officers make mistakes in training so they can avoid and recover from them in an actual campaign.
I don't know enough to know how to encourage an environment of honest mistakes. I guess I know enough to know I want that.