Permissiveness in RPGs
I have this impulse sometimes, I think you might too: whenever a player can get away with something having rolled not one dice, a part of me thinks "this is too easy, we need the element of luck here, otherwise it won't feel satisfactory".
Even now I want to say that this can be true, that a situation can feel unsatisfactory because the player didn't roll a die to get where they are, and yet I can't think of a single moment where I, as a player, would have felt more satisfied about how an event turned out had it been randomly assigned to me by a plastic polyhedron. But you know what has happened before? Me, as a player, thinking through a nice plan, executing it, and then having it come apart because of a bad dice roll.
Still, doesn't it feel weird to be too permissive? To always be trying to say "yeah I think you can get away with this"? I thought so initially, but then I realised that every GM I played with and enjoyed it was very permissive. They would just let stuff fly, work together with the player to fit it into the framework of our invisible rulebook, and not stress too much about something being allowed or not. And yet, I never felt like they were too permissive, why is that?
My working theory is that this is because a "no" is "heavier" than a "yes". When you tell a player they can't do that, their plan doesn't work, or that the dice says no, this will weigh more in their mind than all the times you've said "yes". Whereas when you tell a player they can do that, the situation moves forward, you reinforce the tactical infinity and confirms that the player has the right idea about what is and isn't possible inside the game world - and therefore you can avoid dice in the future.
This isn't for everyone though. Some people, for some reason that I don't understand, actually enjoy rolling dice and don't enjoy "just talking" about it, so a GM being too permissive and not requiring too many die rolls could make them feel like they're not "playing a game". But as to myself, I find that ignoring the little voice that says it "won't be a real challenge unless luck is involved" leads to better games.
For context, this thought came to me at the tail end of last session of Hearts Aglow. The players obtained a magical item that miniaturised them, came up with a plan on how to get inside the fort where the ogres they had to kill were, snuck around it and smartly got around a posted guard by thinking to go through the ledge on the window, climbed upon his canopy bed and stabbed one of the ogres in the neck.
At every step of the way I kept thinking "oh man, if this goes off without a hitch, it will be really boring", but then I thought about it as a player and realised that they had just spent almost half an hour thinking the plan through, debating it, they even compromised morally to get the miniaturising item. If I were in their shoes and the DM went "well the plan won't work exactly as intended because I rolled a negative reaction roll, the guards will now investigate the basket you're in, find you, and take you inside for questioning", I'd be a bit deflated. Notice that the plan would still have worked: from a DM perspective, this was a "yes, but", since you put them inside the fort, just in a less advantageous situation. But from a player perspective, this feels like a "no, and" because the plan didn't work.
Ultimately, not every plan should work, and I won't be saying "yes" to everything the players do, but I don't think a perfectly acceptable plan requires anything else to make it feel satisfactory either. As the DM, introducing a fictional obstacle and having it be surpassed fictionally, through conversation and maybe with a rule here or there if it comes up, is the ideal on how these games should operate. And if the players outsmart you, then it's also fine for them to feel like they're getting away with something they shouldn't every so often.