In 2014, you could only roll CHA once. No retries.@Minigiant
Actually in the rules glossary you can see that duplicates are useful, as you can't use the same approach again. So having 5 skill to use with the influcence action allows for 5 tries.
That was the point of Skill challenges. So everyone at the table rolls in social and exploration challenges.
Fighter rolls Intimidate: Success
Rogue rolls Deception: Failure
Bard rolls Persuasion: Success
Wizard rolls History: Buff
Cleric rolls Buffed Persuasion: Success