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You can indeed speak to a guard with character A, causing the guard to turn around, then switch to character B mid-discussion and use stealth to your heart's content.
The simplest solution is to cast Fog Cloud / Darkness / use an Arrow of Darkness and then pickpocket or lockpick whatever it is you need.
Or, you can summon a creature ( like elementals or undead ) or have a Druid turn into a creature, and it will make most NPCs run away.
Another thing you can try is casting cloud over your target, and robbing them inside of it. Again, use the shift key to be sure, but no one should be able to see inside the cloud if you want to pickpocket.
Turning invisible works as well. Get creative! I'm sure there are other ways to achieve this as well.
Make sure to ungroup the character doing the stealing from the one doing the talking. Bonus for this strategy: your target won't go looking for the thief until they're out of dialogue, and as long as the thief is far away when that happens, they'll accuse the other party members of theft but because they're technically innocent, nothing will come of it.