Running into something in our sessions that I'm not sure how to regulate.

For example, lets say one of my players asks if they can try and convince an NPC of something and I have them roll a Persuasion Check, they fail the check but another player asks if they can try and convince the NPC of the same exact thing and roll their own Persuasion Check immediately after.

Is that against the rules somewhere? I can't really find what I'm looking for.