Bear with me.

There are times, particularly in the art of war and diplomacy when losing as an objective is just as important as winning. There are examples of intentionally losing battles in the short term in order to win the overall war, such as enabling enemies to capture false information or acting as a Trojan Horse to support the success of a final goal at some point in the future. Either way, such strategic thinking while extreme is still an essential part of the job but to do it effectively and convincingly is an entirely different matter. Starfleet often encourages it's officers to "think outside the box" so it seems plausible to me that their may well be training scenarios where victory may be all but assured but needs to be averted at any cost as a part of a bigger plan. With this in mind what form might such a training program take and which officers specifically might have to take such a test to learn what is arguably the much harder lesson than learning how to deal with failure, but rather sacrifice?

Update: /u/toasters_are_great actually cited the specific clip from another franchise that highlights the kind of scenario I am attempting to explain here, credit to them and giving us the link as follows:

Ranger Cranston being ordered to lose on purpose, but to make it look like it's not on purpose.