It's been a while since I've seen this episode - so much so that I think it was a two parter but don't trust my memory. And of course what I remember most are the scenes between Patrick Stewart and David Warner, and the scene at the end..."I saw four lights". Or five lights. Whichever.
I seem to remember however a scene in which Troi told Riker that Jellicoe was not the confident captain that he projected to everyone, that he was consumed by doubt (not her words, probably).
So I see Jellicoe as someone who feels he's in over his head, and needs to have everything go his way, as a way of keeping control of the situation. This kind of captain would probably have changed the Enterprise from 3 watch to 4 watch, instead of from 4 watch to 3 watch, just to make the point that he's in command.
If I were in command of a military unit (or even quasi-military unit) where sometimes lives depend on decisions, I'd want my XO to point out flaws in my plans, possible bad results of my decisions, etc. Which Riker does, but which Jellicoe, especially on first taking command, can't tolerate. If Riker had busted his butt to get everything switched over, he might have earned Jellicoe's trust and been able to trade on that later with a "But, Captain, have you considered..."
Bottom line, Riker and Jellicoe were both too stubborn.
"Having is not so pleasurable a thing as wanting. It is not logical, but it is often true."