I think the con prep mentioned here was John Harper's, but I might be wrong. It was two questions: "Who's in charge?" and "who's the thorn in his side"?
Based on that setup, here's my take on distributing the first two playbooks.
Who's in charge? [to that player] Why? Is it because you own the place (Maestro D')? The whole town, maybe (Hardholder)? Is it because you can offer people hope (Touchstone)? Cash (Operator)? Protection from your thugs (Chopper)?
If they chose the Maestro D':
So you've got this place, sure, and you have people working for you. One of them you can't bear to be without, but damn if you trust him. Who is it? [to that player] Is it because you're just too sexy for his own good (Skinner)? Too tough to give a damn (Gunlugger)? Way too freaky (Brainer), or carrying way too many freaks around him (Hocus)?
If they chose the Hardholder:
So it's your town, and you call the shots. But it's never so simple. Who's the biggest thorn in your side? [to that player] Is it because you don't take orders and you don't take shit (Battlebabe)? Is it because you always want what others have (Hoarder)? Or are you full of too much ambition, always working your own angle (Operator)?
If they chose the Touchstone:
So you've got the vision, but that's never enough, is it? You depend on someone else to make your vision come true, and you don't like it one bit. Who is it? [to that player] Is it because the people who follow him listen to you instead (Hocus)? Because the world speaks to you in ways that he can never hear (Brainer)? Because you're the only one who can build and understand the tech that'll make it all work (Savvyhead)? Or are you simply the one with the guns, who won't be afraid to shoot anyone for the sake of the vision, not even him (Gunlugger)?
If they chose the Operator:
You've got this operation, and it keeps you afloat. You've also got this team [points at the group] working for you. Who's your right-hand man, and why does he scare you shitless? [to that player] Is it because scary is the only word that describes you (Faceless)? Because you don't take orders, and you don't take shit (Battlebabe)? Because your only real loyalty is to the road (Driver)? Or is it because your body is the real bread-winner, and without you he'll be nothing (Skinner)?
If they chose the Chopper:
Okay, so you're big and scary and everybody [points at the group] knows you're the boss. One of them has a problem with it, though. Who is it? [to that player] Is it because you're bigger and scarier than him (Faceless)? Smarter (Savvyhead)? Is it because you're the one who has to clean up after his violent shit (Angel)? Or are you taking your orders from a higher authority (Hocus)?
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Afterwards, spread out the rest of the playbooks before the other players and ask, "what about you? what's your story?".