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You can't advance that quest if Hancock is a companion since he won't speak the dialogue that advances the quest. Just dismiss him, and speak to him then. It should solve your problem and you'll be able to continue the quest.
Well, when my options are just the standard talk options... what am I supposed to do?
"Hancock will stop progression of the quest with a Deal with Bobbi loop if the player character spared or killed Bobbi after The Big Dig quest and refused Hancock to be a companion on "Meet with Hancock as the Shroud". This can be fixed by adding Hancock as a companion, and then talking to him as the companion." (Wiki)
What I did and it worked for me was:
Have Hancock as a companion, Talk to him while you're dressed as the Silver Shroud and listening the Silver Shroud radio station on that aimless spot (objective) on Goodneighbor.
He did talked about the subject (being a silver shroud) and so on, more dialog appear until the objective changed to kill Northy and Smiling Kate.
Hope it helps.