Have you ever been straight forward with your leadership regarding a bad idea or decision?

I recall during a battalion staff meeting (I was the company operations sgt) the battalion commander made a decision to put all of the MPs on duty on 12 hr shifts in full body armor during the dog days of summer. His purpose for this was to free up a squad for (training) since he mistakenly told a superior officer that he had MPs in training which was not the case. All of the leadership in the room seemed to be supportive of the decision. I on the other hand did not. At the time I was also the unit safety officer, master fitness trainer among other additional duties. All of the available MP were already tasked with missions and this was an untenable order. I couldn't help myself and without hesitation or more accurately after a quick assessment about how what I was about to do was gonna affect my Commander and my 1SG I opened my mouth. I stood up and suggested that everyone in the room which equaled a squad should dust of their gear and personally stand in the place of our soldiers to assess the effect this decision would have on our soldiers to save face for the Bn Cdr. The glares I received from the leadership in the room was priceless. Except for another Sgt Morales Club member who happened to be the S3 operations Sgt everyone else was not supportive of my recommendation. The short of is the order was rescinded until I retired. I was sad when I saw a lone MP standing a gate the following year in full body armor on a gate which hits cat 5 heat by 9am. Hmm new army?

I've always had trouble sugar coating things. It was an aweful triat for an E4, but has served me well since. Besides, I need to practice up for my future career as a curmudgeon.

YUP. The reply was that an E8 said "I looked at your record, you were recommended because you know your stuff and will tell it like it is. The E7 then told me if "I ever question anyone E7 or up, I will get an Article 15".

Wrong thing to tell me with just weeks left on my contract. I gave up my career at 10 years. Got a great job at a big corporation for 17 more years.

I posted my most egregious example in another of your threads, I think. I refused a helm order from a harbor pilot, once, that had the potential to end badly.

Command Master Chief = Salty

I used to be far more outspoken that I am now (can you believe it's possible?).

I often wondered whether the chain of command had any appreciation for it. When I left he Army, I joined the LAARNG. At the end of my service, the CO took me for a walk. He advised me that I would regret leaving (NOT!). He also expressed his appreciation that I was honest with him, because most people tell commanders what they want to hear rather than the truth. Until that moment, in all the 3 years I knew him he had never shared that perspective with me. We probably would have gotten along better if he had. I didn't tell him many things, but when I went to him I was ALWAYS honest.

He also offered me a promotion if I would stay.

During my 20, I often questioned my COC. Whether I was right or wrong, I often paid the consequences. Sometimes, I was rewarded. Now, 21 years AFTER my retirement, I've had plenty of time to reflect and learn from those experiences. Some thoughts:
In your particular job, you must be the expert, and be decisive. But on all other issues, remember that the admirals, captains, and large ship commanders are about a million times more experienced and more well informed on the socio/political and strategic issues. Plus, they did not get to their level of responsibility by allowing someone to put a chink in their reputation for leadership. So before you question/suggest or just get involved in an issue, ask yourself Is it MY responsibility to be involved? If you decide that the ship is sinking (figuratively) and you feel you MUST get involved, decide what you want your reputation to be as a result of your involvement: Are you going to be the hero who helped solve a mission-critical problem or are you going to end up as the guy who distracted the COC from their priorities, just to satisfy your need for validation?