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Originally Posted by Jovus
I'd use the rule of three that tends to get used unofficially in extended Contests for cases such as poison and stuff in certain worldbooks.
Have the would-be assassin have three contests with the target. After the third contest is won, the assassin is considered to be in position. If any are failed, the target notices. If the assassin makes a critical success, that voids the necessity for the next (or for all subsequent) rolls.
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My problem is that it artificially deflates their skill level. Having them roll several times on a "fail a roll and you're in trouble" task effectively lowers their skill, so for some reason, characters need a higher stealth skill than what the normal bell curve + modifiers would actually suggest. It twists probability such that it's harder to instinctively calculate your chances for success. Rolling once for sneaking right up behind them allows you to tell how close they CAN get before getting caught by looking at their margin of failure. And it only takes one roll.