Maven - Use a Rabbinical response every time except when talking to Rajshree Lauder (Note that you may have to use the Rabbinical response the first time when she asks whether you know Jack. I am not entirely sure whether this is required for the achievement but I got it when I did that.)
Meshugga - Kill Joe Demarco
Mensch - Spare Joe Demarco
Kemfer - Don't get hit during the fights with Joe Demarco and Amos Zelig
Heflekh - Don't use Rabbinical response with Rajshree Lauder
Mutshe - Question Amos Zelig about his involvement with Ethan Goldberg and Jack Lauder's deaths
Klug - Combine two clues
Shonda for the Goyim - Kill Joe Demarco and Spare Amos Zelig
Ubermensch - Spare Joe Demarco and Amos Zelig
Shmulky - Kill Amos Zelig

I think I used the rabbinical response only sparingly until the end. First on the subway station I answered Joe DeMarco with a question every time (this being the only way you can get through the whole sequence without him swiping the knife at you), and then did the same with Zelig when I got to his place before being led to the balcony. After this I got the achievement. So I guess it only matters if you do this by end game, or in some lengthy sequential fashion? Hmm...

Oh yeah, and spoilers aplenty here, obviously.

Thanks. I want to go back and snag these. Loved this brief, but totally entertaining game!

That could be the case, since the description of the achievement is "The best at what you do".

Just for further documentation, I was able to get Shonda for the Goyim by allowing Amos to kill Raj, but then sparing Amos. Joe DeMarco was still alive, but never entered Amos's apartment.