iserith
Magic Wordsmith
As an example, the rogue attempted to hide behind a pillar with a roll of a 13 on one round and a 15 on the second round. The NPC the character was hiding from was a umberhulk, which has tremor sense. After the first round the player thought the umberhulk may have a high perception. After the second round, the player came to the conclusion that the umberhulk has tremor sense. Now that the player was aware of this I indicated that additional detail on the hide attempt to conceal from the tremor sense could make the attempt successful. The player suggested there wasn't a way to do this, so we moved on.
The way I would handle a situation like this is to telegraph that the umber hulk has tremorsense when describing the environment. Perhaps how its head snapped left and right to unerringly focus its scintillating compound eyes on anything that traversed the ground or something like that. Attempts to hide from it while remaining on the ground would not result in an ability check - the character simply fails. Asking a player to roll when the only possible outcome is automatic failure is a little misleading in my view because it gives the impression that there's a chance of success. This can result in subsequent, fruitless attempts by the player and additional failure.