I spoke to the 'weakling' fella and found out he wanted me to get everybody to be nicer to each other. I walked over and talked to everybody else and my dialog choices with all of them were as if I'd had my initial conversation with them. As if they had already given me their suggestions for improving the squad.

I couldn't get this one to work either, now I'm trying to buff up my explosives level so that I can just talk to Mags and get the quest done that way instead.

I had to ask the misfits what they thought about the team again to get the speech check to show up. Slightly ass-backwards way of doing it, but it's there.