Blades in the Dark has a pretty fascinating approach that comes from the unique way is resolves actions in general.
If you sneak as a group, it is done as a group action. Everyone rolls, and the best roll in the whole group is the result for the entire group. Sneaking with several PCs actually makes it more likely to succeed than going at it alone. (Which of course makes more sense with most other actions, though perhaps seems a bit weird with sneaking specifically.) However, as a downside, every PC in the group whose roll is a failure causes the character leading the group to take 1 point of stress. Stress is a pretty unique mechanic in Blades in the Dark (and other Forged in the Dark Game). In these games, players can at any time declare that the bad outcome of a roll is actually not as bad as the dice made it look, and the consequence can be shrugged off and the character is fine. But that always costs you stress. And once a character's stress reaches the limit, things get bad. The character is out for the rest of the adventure and will suffer a permanent mental mark for the rest of the campaign.
For a character who is leading the party in an attempt to sneak past guards, you have a pretty high certainty that you will get past the guards undetected. But he's the one who is probably going to have to pay for that by not being able to avert other disasters later in the adventure.