Oooh, I’m actually interested in seeing this thread, hope it’ll get a good discussion going!
For me, whenever I either give feedback or plan and DM events myself, the most important thing is to allow the characters to shine. The worst thing a DM can do is force rolls where they shouldn’t be and make a player say “But my character would never fail at that”.
Now, the one exception for this is combat, of course, you can roll low and not hit any enemies. It’s up to you to make a believable emote for what your character is doing. If you’re salty about your low roll and emote your character being incompetent, that’s solely your fault, not the DM’s.
But, say, a character is throwing a dagger at an unmoving target. The DM makes the player roll, for some reason, despite the character having previously been established as competent at throwing daggers. This, in my opinion is a mistake.
Rolls are great, for as long as they represent luck, and not the skill of the character.
Once we get that down, we can move on to actually planning events. For me, I prefer planning only loosely and making very few notes. I don’t plan combat at all, for example, because I never really know how many people show up to my event (it’s a bit of a wild card in who can and cannot attend) and I’m fast thinking enough to be able to tweak numbers according to how well people do and how many attend.
If I see them ploughing through everything effortlessly (when that’s not supposed to happen), I just make the enemies hit a bit harder and take more damage before going down, or even get them reinforcements if the plot allows for it.
I also don’t overly plan out the plot and only write opening dialogues.
Of course, I have an idea on what’s supposed to go down and check out locations beforehand, but I always want to let the players feel like they can influence it. If they want to spare a hostile NPC after defeating them or talk their way through a group of enemies, I give them the opportunity to do that.
I’ve never liked any of those events that where the DM is just looking to tell a story and you either have to get insanely high rolls to try influencing it or you were just told OOCly that you cannot do what you were about to do.
I never tell my players “you can’t do that.” Ever. If their characters are going to do that, then they should do that.
I might punish them hard for it, granted, if they do something stupid, but I’m also usually willing to skip entire sections if they’re smart and find a way to bypass them. So it balances out nicely.
EDIT:
Typos.
Also, another good example for a DM’s poor judgement about asking for rolls is spellcasters. Say, you’re playing a demonologist and your character has previously been very well established to be a skilled summoner. The likelihood of them failing at summoning a demon which they regularly do is quite frankly, null. But the DM makes them roll for it anyway and they roll low. How does that happen then? As I’ve previously stated, that’s a roll determining character skill instead of player luck.
Which I find to be poor DMing.
Also, another good example would be basic actions, such as climbing up a cliffside. It’s okay if people want to make personal rolls for it, because their characters aren’t skilled rock climbers, but if there’s a rogue, hunter, monk, demon hunter or whatever other character that’s supposed to be agile and would perform the action effortlessly, then they should not, under any circimstances roll.
Although this example can be bypassed by just making a minor rockslide and making them roll for dodging rocks, the general point is still there, I think.