Have you been involved in a situation where you had to confront a superior about their conduct?

Happens to O's too. I was a flying squadron commander and my group commander planned to take a mission trip with one of my crews, just happened the destination was DC where his family lived. As we approached the mission date, I asked him if he had submitted the leave paperwork (twice) and he shut me down, twice. Then as he stepped to the jet I asked him again, and he said, "I told you not to worry about it!" Only he didn't file leave paperwork, didn't get leave in conjunction with TDY approved, took my crew's rental vehicle to visit his family, and then attempted to charge it all on the travel voucher. Once the crew returned and I got the debrief and the vouchers, I took them to the Vice Wing CC. He called in the PACAF JAG, swore me in, and the formal process started. In the end, he was relieved of command and transferred, my record was protected, and everyone in that Ops Group was a little better off.

Ah confronting a superior, been there done that got the T-Shirt and the favorable actions blockade. The biggest problem with confronting a senior Officer or NCO is the delivery in some way that also translates the other way when you talk to peers and subordinates. Keeping in mind this is me talking and I can only offer my opinion, the biggest issue is checking and double checking to see if your observation is right or without context. If I had a nickel for every time I was approached and given the 50 question and personal opinion about the way I performed my duties or lead I would be a rich retired old fart. With the advent of the internet and social media many find it easier to blast accusations and unit business out there like a mini gun with an infinity belt. A good leader that you approach correctly will listen, evaluate your observations and make adjustments if needed and you have no fear of repercussions a bad leader AKA a TOXIC leader will stop you mid sentence lose their temper and either outright threaten you or blind side you in evaluations promotions or a transfer regardless if you are right or wrong.
*********EVERYTHING BELOW THIS IS JUST RAMBLING DON'T WASTE YOUR TIME********
I became very confrontational when I hit SSG the first time, I lacked tact, proportional response and people skills. I would say I had about a 10% success rate then. But I think it had to do with the leaders I was dealing with an not my asshole ways. Later in life and service and closer to retirement, I developed people skills,a modicum of tact and minimal proportional response but I was still an asshole but my success rate at discussing alleged inappropriate behavior or actions shot up to 70%. I once developed a non stop campaign to stop a COL from destroying a unit in which I was assigned. His toxicity was worthy of Superfund status and I approached him daily offering advice, examples and recruiting CSM's and other SNCO's in a major attempt to get him on track before he destroyed the unit. I was respectful, I offered sound advice that was easy to verify and the constant barrage of great leaders in the unit caused him to do a hold my beer moment and conduct a HELMET INSPECTION (YOUTUBE VIDEO) of which I had ZERO to do with other than being in it, which in the end caused him to retire.

It's all a throw of the dice, if you are lucky you will get a good leader who will listen and thank you for your views. If you get a bad one then you may find a bumpy road ahead if not a short enlistment.

You will have your good leaders and your shitty ones. The hardass ones were my biggest pain because they were trying to teach a hardheaded ass (me) what needs to be done, either by doing it to me, or forcing my hand when dealing with others. If I could do it again, I wouldn't have changed anything. My good leaders were just that....mentored you, encouraged you, and they are something you get to take for granted after awhile. You KNOW they're good. But the dickhead leaders are usually the ones you remember especially when you look back and wonder were they dickheads due to personality issues, or were they dickheads trying to use hard love to teach you a hard lesson now, that you can use as a tool later? Looking at mine, I had both, but the hard love leaders who pissed me off daily, who counseled me using "choice words" and "exercise with louder choice words", threatened me with Art15 (co and field), and took me down a peg, were the ones I wanted to remember later. I'd buy them all a shot of whatever they'd want if I could now. I see who was at fault, and it wasn't always them. Know yourself and seek self improvement. The first check starts with you before you go to them.