Looking on Dulfy's site, like Ahrngrim suggested, at http://dulfy.net/2015/10/21/swtor-alliance-specialists-and-companion-recruitment-guide/#The_Forgotten_Trophy_Major_PierceM1-4X, suggests choice #1 is for completing 20 warzones, choice #2 is for having 40 valor, and choice #3 is "still working on it," if you want to try a workaround.
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At least for the valor way you need to talk to him twice.
Getting the Quest I think, and then recruting him.
