My single biggest failure as a Divo was the time I sat on a Sailor's leave chit because I was literally afraid to route it up to the XO and CO, the delay in doing so ended up costing my Sailor $1,500 (was traveling w/ wife and two kids).
Long story short, I'm not a coward per se, but the command climate was so toxic where all leave chits were routed to the CO and many were not approved, and there was a guarantee that both the XO and CO would rain down hell upon you for even bringing one to them in the first place. I was an unqualified Ensign at the time, and I definitely acted cowardly in that situation.
As hard as I thought getting the chit through the CO was, it was way fucking harder to admit to my Sailor what I had done. I sat down with him 1-on-1 to apologize and I was very fortunate in that he accepted and it did not ruin our working relationship.
Ultimately, I was lucky in that my Sailor was an E-6, pretty well aware of the command climate, and a solid guy all around. I wish I could have learned that lesson in a less costly way, but I'll be damned if it didn't give me strength to endure the CO and XO shenanigans when it came to matters involving my people.