Sentences like “Can I roll for persuasion?” or worse “I perception the room” are one of my biggest pet peeves coming from players. Tell me what you want to accomplish, I will tell you whether and what you need to roll. I’ve mostly managed to train that behavior out of my players, thankfully. As a newbie DM I used to use die rolls as a crutch – “this is a dice rolling game, so the more dice we roll the more fun we’re having, right?” I thought. I also hated saying no to my players, so stupidly high DCs were a way to shift the blame onto the dice for my players’ failures. As I’ve gained experience, I run a much less dice-heavy game. I very often just let my PCs succeed with no roll required.

The one case where I don’t mind the players asking to roll is when they ask to “INSIGHT CHECK” à la critical role; it’s always fun to see the players so passionately engaging with NPCs.