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Guest 6801328
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Very true. I was thinking particularly of situations where the potential observer is itself hidden (or otherwise unobserved), but I didn't emphasize that in my post.
As an example, if a PC is trying to move through a crowded riot without being identified by anyone who is looking for her, she will likely need to make a stealth check. If you wait until there is someone looking for her nearby to call for the stealth check, you reveal such a person is nearby. Whether that's better or worse than the player knowing in advance whether the character is doing a good or a bad job is definitely a matter of opinion.
Maybe use "passive" Stealth? (Or, really, Deception or Disguise Kit in this case, perhaps?)
On a related note, the other day I wanted to forge some documents for a ruse, and the DM had me roll Forgery Kit. I rolled a 22 and we went with that, but I was thinking to myself, "And why wouldn't I just keep trying until I got it right?"