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https://www.youtube.com/watch?v=ibKhrIEHX_0&feature=youtu.be
There are moments where he reminds you of discretion after a mission but I don't know if that can be avoided. (e.g. "killing" the Murdower Hotel receptionist might annoy your employer)
Not sure if you have to trigger absolutely everything to piss him off, but there isn't that much you have to do and only a few missions must be played in a specific way for this.
I got the receptionist killed
I spoke to electrohead
I told him ♥♥♥♥ you whenever I could and interrupted him all the time
I killed everyone in the prison level
what the hell am I missing
Did you try refusing the drug after killing electrohead?
I never got a choice to refuse a drug
After the Electrohead mission you can talk to your therapist and refuse the drug if you pick the right dialog options. It seems to be the only thing you're missing to get the achievement.