Scrap 'initiating' on someone.
Create a fun roleplay scenario, make up the context (you need it to fund an ill siblings medicine/you've an obsession with socks etc) and then ask them to comply with your demands. If they're unarmed, you can state that you'll 'cap' them in their knees if they don't follow suite, or that you'll simply shoot them in the chest and they'll be history!
Ask them to put hands up (which is Shift J for them)
If they comply, run up and scroll wheel for the option to steal wallet.
If they don't comply, K.O them with your gun (shift G) and steal wallet that way.
if you want to be more elaborate and steal more, either shift G them or get them to shift J and restrain them, alternatively make them lay down (with 15k zip ties) and rifle through their pockets.
if they're compliant, simply ask them to drop item X Y Z and then run